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Land Your Dream Design Job

A guide for product designers, from portfolio to interview to job offer

Dan Shilov

Whether you're looking for your first job or your fifteenth, you can find an opportunity that plays to your strengths, matches with your values, and provides support for professional growth.
250 pages and 231 links — last update 6 months ago

editione1.0.0

Courtney NashEditor

Introduction

I have a confession to make. Early on in my career I was terrible at interviewing. I would take months obsessing over every pixel in my online portfolio only to fail in the last round of interviews. That is, if I got lucky to get to that final round in the first place. Most of the time, after submitting my application, I never heard anything back. As a designer I was comfortable generating ideas on a whiteboard with colleagues, but doing a whiteboard design challenge in front of an interview panel gave me performance anxiety. And don’t get me started on the take-home design exercise assignment. Trying to read the lines of what the company was looking for while balancing a looming work deadline always put me in a tight spot.

Much has changed since then. Over the past decade I’ve personally interviewed with many companies, from small startups to large corporations. Beyond my own experience of interviewing, I had the privilege of being on the other side of the table. I conducted app critiques, whiteboard challenges, sat in on portfolio presentations, and talked with countless designers and design managers. If there was one thing that I learned, it’s that everyone struggles with interviews. Even senior candidates—strong in their craft with years of experience behind them—tend to hit some speed bumps in their interview process.

Designing is hard. We spend considerable time, effort, and money learning the craft, whether it’s through traditional education, new boot camps, or on the job. We invest time in our education because we believe the payoff will be worth it. But when it comes to looking for work, we frequently find ourselves on our own. Unfortunately, the job search and design interviewing process can sometimes feel just as mysterious, understood only by a select few. It can feel downright elitist. And, of course, the lack of feedback on how we’ve done or what we could have done better doesn’t help.

But it doesn’t have to be this way.

With the right approach we can take control of the job search process to land a role that’s both exciting and helps us grow. You can improve your interviewing skills and communicate in such a way that puts your best foot forward to let your skills and talents shine.

Who This Book Is For

This book is geared toward individual contributor designers who are looking to transition to their next or first role. If you’re a current manager or a manager-to-be, you may still find this information useful, but note that this material doesn’t cover manager-specific design interviews.

confusion Throughout the book, for the purpose of brevity, I use the term “product designer” as a catchall for various industry terms such as “interaction designer,” “UX/UI designer,” “experience designer,” among others.

New Designers

If you’re starting out as a designer, congrats! You’re on an exciting journey. To set you up for success we’ll look into strategies for approaching the job search in a way that gives you more autonomy. I recommend paying close attention to the first part of the book, which will help you think through your ideal role based on your strengths, growth areas, and interests. Starting with the end in my mind will sharpen your senses and get the most out of your search. And of course, the book is chock full of interview examples to help you on your journey.

Experienced Designers

You may think you already know how to prepare and what to expect from interviews, having been through the process a few times. This may be true, but design expertise does not always equate to excellent interview performance. So don’t leave this to chance. Whether it’s how to represent yourself during your final presentation or how to solve design exercises without missing a beat, you can skip around to sections that you may need more practice on or are looking for ways to distinguish yourself.

Teachers, Mentors, and Design Educators

Having been once a design student, I know the value of a solid education. Nothing beats dedicating the time and effort to learn design through and through. But beyond classes, few design programs help students in navigating the world post-graduation. Unfortunately, too often, students are left to their own devices. This book aims to bridge the gap between the two worlds—academia and professional practice—and will give you useful information for helping today’s students succeed in the competitive marketplace.

What Is Covered

This book takes the approach of covering the product design job search process from beginning to end. It’s meant to be your guide throughout the process, from when you first start thinking about where you want to go all the way to how you can create your new job and get up to speed quickly—and it’s chock-full of tips in-between.

You don’t have to read the book from cover to cover. In fact I encourage you to skip around. Go to the sections that are the most relevant to you now or where you need the most help.

  • Part I: The Modern Product Designer. Before firing up that portfolio, it helps to first understand who you are as a designer. We’ll look into skills and traits and of today’s product designers. We’ll also do a detailed breakdown of key job characteristics you should consider for your next role. By defining your ideal role upfront, you’ll be able to tailor your application thus increasing your chances of landing the dream job.

  • Part II: Taking Action and Finding Opportunities. We’ll build on the previous section by uncovering your superpowers, which will lay the groundwork for your pitch. You’ll use your pitch across various channels to communicate your unique competitive advantage as a designer. I’ll show you how you can tailor your portfolio to practically speak to your strengths. Lastly, we’ll cover several strategies for how to apply to roles.

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Part I: The Modern Product Designer

Product Design Skills, Traits, and Responsibilitiesan hour, 16 links

Product designer. UX designer. UI/UX designer. Interaction designer. Experience designer. There are just some of the many titles designers call themselves these days. But look deeper and you’ll quickly realize that one company’s product designer is very different from another’s. Before diving into titles, it helps to step back and start by asking yourself:

  • What type of designer are you?

  • What are your strengths and what are your growth areas?

  • What traits are second nature and what doesn’t come as easy?

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What Does a Product Designer Do?

The design industry has evolved significantly over the last few decades. Significant innovations in mobile computing have increased design scope to native and wearable devices. Larger tech companies translated psychology principles with the help of design into engaging, and at times addictive, products. All of this is to say that the roles and responsibilities of designers have significantly changed over the last few years.

The titles of design have also evolved. Previously, specialist skills present in roles such as web designer, service designer, interaction designer, UX designer, UI designer, and information architect are now commonly seen collapsed under the title of “product designer.” This sometimes adds more to the confusion since product design expectations vary by company.

confusion To keep things focused and less wordy, throughout the book I’ll be using the term product design to refer to UX/UI design as well.

While the definition of a product designer is in flux, here are some general things to keep in mind if you’re applying for this role:

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What’s Your Design Shape?

Different models exist out there to map out design skills. It’s a rough science and more of an art. IDEO popularized the T-shaped designer—someone who has deep knowledge and expertise in one or two areas (for example, interaction design and research) but has broad knowledge of other areas (for example, service design and brand design). Larger companies, usually with bigger teams, are composed of a mix of designers. Some of those designers tend to be I-shaped—deep specialists in their domain (motion graphics experts, for instance).

Figure: Assessing Your Design Skills

Assessing your design skills

The modern designer will typically have a variety of skills at their disposal.

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Creating Value in an Organization

Beyond understanding your own skills, you need to also think about how your skill sets translate to the needs of an organization. At the end of the day, you’ll be hired to solve another company’s pain point that they are not able to solve themselves. These pain points vary, but there’s some consistency depending on the company’s maturity.

Smaller companies, such as startups for instance, can’t afford to hire many designers, so they typically bring in a senior generalist to start. Typically this designer will have a strong grasp of interaction design and research, and some visual design skills. They’ll help establish a design direction for the company and ship product, while integrating design process into the product development cycle.

Figure: Assessing Design Team Skills

Assessing team design skills
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Craft Skills

To do strong design work, you have to be well versed in fundamental skills. It’s a prerequisite for the job. This is the raw ability to take inputs and transform them into something meaningful based on your technical knowledge of tools and concepts.

Craft is your knowledge of the tools, methods, and techniques to get the work done. A good designer has a solid grasp of the fundamentals that are usually studied in school, but not everything will be or is expected to be mastered at an academic setting.

important The most important skill of all? Learn how to acquire new skills or renew existing ones as the design field changes rapidly.

From a craft perspective you need to think about acquiring skills in these areas:

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Collaboration Skills

Design is a team sport. A designer is powerless if they can’t communicate what they’ve done and if they can’t work well with others. Strong collaboration and communication skills are key throughout one’s journey as a designer.

Initially, entry-level designers focus on smaller features and work primarily with oversight from a senior designer. As one’s career progresses, the scope and complexity increase. While strong craft skills are still a prerequisite, one’s focus shifts toward influencing others and working with other cross-functional senior leaders on ambiguous, long-term projects.

Cross-Functional Partnership

There are various models of how a designer fits into a company’s org chart. One of the more popular models these days is the squad model, where a designer, product manager, and a technical lead all work together to establish the team’s day-to-day and overall long-term vision. However, sometimes you’ll also frequently work with other specialists, such as researchers and data scientists. If this is a multi-team project, you’ll probably have regular syncs with the other teams and it’s not uncommon to interface with non-technical counterparts such as folks in sales, legal, operations and so on. You’ll be working closely with the team to get your work shipped. Unless you’re also an engineer, most likely you’ll need developer support to get the thing you’ve designed built.

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Strategic Skills

Should designers have a seat at the table? It depends on the organization and design maturity—some already do, while in companies with low design maturity, designers are merely decorators late in the process. But what does it mean to have a seat, and what’s expected of designers who create value beyond producing deliverables?

At its core, strategy is choosing what to do and what to leave out. It’s about deliberately prioritizing limited resources (time, money, people) to create value.

Not all designers will engage in strategy. Typically this is the domain of product managers or senior-level designers. Some designers might even eschew strategy altogether in favor of being a master at craft. There’s nothing inherently wrong with that, but if you do want to grow your influence in a company, then understanding the business, how it makes money and how design can help, will help you advance rapidly in the organization.

When you’re interviewing, demonstrating that your work has led to success will make you stand out. Yes, it’s hard to get crisp data and many designers struggle with showing results of their work beyond the deliverable. If you are in this situation, follow up with your team. Get the data. Get the information you need; not only will it be important for interviews—it’s important as a feedback loop overall.

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Professional Traits

Aside from having a well-honed skill set, designers possess traits that help them get quality work done while elevating people around them to do their best work. Strong designers raise the quality bar and are seen as leaders to emulate due to the positive examples they set in the workplace. Examine the following traits.

Growth-Oriented Mindset

Design is a team sport that continues to evolve and rapidly grow over time. No one knows everything, but how you handle the lack of knowledge makes a key difference. Having a “growth mindset” (as coined by Carol Dweck) as opposed to a “fixed mindset” helps you continue to push when the going gets tough and to learn from failure.

Designers with a growth mindset:

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Prioritizing Career Growth

As you can see, the modern designer possesses a tremendous amount of knowledge about various aspects of design. If you’re starting out in your career, don’t worry, you don’t need to know everything all at once! Naturally, there will be some areas you’ll gravitate toward and enjoy, and others where you may need to pay extra attention in order to improve.

If you’re an entry-level designer, the core expertise and strength that you should bring to your team lies in your craft. This means you should be spending more of your time on the tactics and execution, getting stronger and faster with production. How companies determine your level of craft will vary and this is a good conversation to have with your manager. But in general you’ll probably want to hone in on your interaction design and visual design skills. When you have the basics down, you should pay attention to execution and strategy. All of these things take time, so don’t stress out if you don’t feel like you’re growing as fast as you’d like. It usually takes a couple of tries on multiple projects to improve your skills.

As a senior designer, your work will be more strategic. You may not be pushing the pixels as much day-to-day, but you’ll find yourself in meetings and strategy sessions. You’ll be responsible for leading the team toward new ideas and innovations on par with your product manager and engineering lead.

There are of course exceptions to these rules. In larger companies, for instance, there are dedicated specialist roles for visual designers, interaction designers, and motion designers If you’re working at a small company or a startup, you might find yourself stepping into strategy more often than not, and doing the design, while also running research studies and maybe even coding some of the concepts yourself. For some designers, this can be a nightmare. Others will relish the opportunity to do multiple things at once and learn a lot. Ultimately it’s up to you to decide what’s the best fit.

Defining Your Ideal Rolean hour, 25 links

Being intentional in your job search will help you find a job that’s a great fit. Defining what your future role should look like will help you dismiss options that don’t fit with that vision and help you make decisions that are based on values that are important to you.

If you’re just starting out in your career or you’ve been recently laid off, it’s tempting to jump at the first offer, end the search, and start doing the work. Of course everyone’s circumstances vary, and if that first offer checks all the boxes for you, then definitely pursue it.

The trouble comes sometimes when we haven’t taken the time to define those boxes. In those circumstances our opinion may get swayed by shiny things like the perks that companies like to advertise: happy hours on Fridays, various discounts, Ping-Pong tables, and so on. While these may sound cool, the reality is that they might not be applicable to you at all. Maybe at this stage of your career what’s important to you is mentorship, guidance, access, and the ability to work with senior professionals closely so you can level up and grow quickly.

Finding a Job That Fits

This is why it’s important to define your own criteria when looking for a job. Let’s apply the jobs-to-be-done framework by Clayton Christensen. Don’t think about getting any job—think of hiring a job for your needs. This will help you identify a company that can support your growth and help you reach your potential faster with wind at your back.

Think through the company’s characteristics that are important to you as if you’re evaluating a candidate. What makes them great? Who would you pass and who would you hire? Not all of these characteristics will play an equal role, and you may choose to include others, so treat this list as a starting point:

  • Design maturity of the company.

  • Your future manager.

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How Design Maturity Impacts the Type of Work You’ll Do

A mature design company has internalized and established proven design processes that it has honed over many years. Design is not a layer sprinkled at the end of the product development cycle but an integral piece at the heart of the process, a core competency that’s well funded and properly staffed.

Table: Design Maturity Tradeoff

Low maturity companyHigh maturity company
Opportunity toEstablish a practice of design from scratch in-line with your vision, go beyond the work and shape process and design culture.Focus on the core work and develop strong individual contributor skills in craft and collaboration.
Best suited when…You’ve been in industry for some time; you can do the work.You’re starting out and need guidance and mentorship.
You’re interested inOperations, processes, design management, policy, and governance.Improving your core individual contributor design skills, focusing on deliverables.

High design maturity companies are great places to learn quickly and with rigor. You can continue to stay and develop your skills further to become a skilled specialist (that is, design lead) or a manager. Alternatively, you can seek a different challenge altogether by going to a low design maturity company to build the design culture there.

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Your Future Manager

Your future design manager will play a key role in your career. They will have the final say about your performance. In many companies a combination of peer and manager reviews are common, but at the end of the day, the manager wields a significant amount of influence. They will ultimately decide how well you’ve done compared to your peers and whether your performance was satisfactory or not.

While we sometimes think of managers as omnipotent supervisors, the reality is that we still have control over who we decide to work for. In fact, during your interviews, you want to think of interviewing your manager as much as they’re interviewing you. What kind of manager would you like to hire? Think about the skills that you’re trying to improve and how they can help.

The Design Manager

Having a manager who’s come from a design background can be helpful. If you’re just starting out in your design career, they’ll get you up to speed quickly on the craft side of things. But not all designers make great managers. Some may have turned to management reluctantly because it was difficult for them to advance otherwise. So when you are interviewing with a design manager, take note how they show up and the type of design team culture they’ve established (more on that in the next section). In the later stages of your job search when you get an offer, be sure to talk with other designers who currently work with this manager or have worked with them in the past.

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Assessing Company and Design Culture

Trendy Ping-Pong tables, fun swag, cool off-sites. Some of these things may come to mind when we reference a company’s culture. In reality, perks are just surface characteristics of a culture, which usually runs much deeper—it’s the way things get done in an organization. Some companies may look great from the outside, but inside the reality is different. When interviewing for companies, it’s important to find out the real deal (usually by interviewing the company after you’ve got your offer, and at the same time it helps to think about companies’ characteristics that are important to you—that is, which environment aligns best with your values.

How do you determine a company’s culture? One way to understand culture is by looking at how the company wants to present itself. Usually that’s a company’s mission statement or its list of values. But beware, what’s preached is not always practiced. To ensure it performed at the highest level of ethics, one company put together a statement of human rights and espoused values, such as respect, integrity, communication, and excellence. The company, Enron, is now a popular case study in values gone wrong—the value they rewarded was the opposite of what was written.

One way to think about a company’s culture is through its actions. How does it get things done?

Company: Moving Fast Versus Approaching Things Deliberately

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Designing at a Large Company, Agency, or Startup

In-house (big company or startup) and agency roles offer different advantages. This is a simplified model, but it should give you a rough idea of the work you’d be doing at those types of companies.

Table: Types of Companies

NameBig companyAgencyEarly stage startup
IndustryYou’ll gain deep expertise and, depending on the company, may work within a limited subset of industries.At an agency (unless they’re specialized) you’ll work with a variety of clients who come from different industries.You’ll become the in-house design expert, knowing the ins and outs of your industry and how it relates to the company.
Variety of design projectsIn a large company this will be highly dependent on the team. However, the benefit of large companies is that you have many teams to choose from.You’ll be exposed to different clients and organizations. Some engagements last a week and others may last months, but variety is usually the norm.As the only designer or as part of a small team, you’ll have your hands full in a variety of design projects for the company from product, to brand, to marketing, and so on.
SalaryTends to be higher as large companies are sustainably profitable.Usually runs lower as service businesses aren’t easy to scale and most of the cost is due to human resources.Most of your compensation here will be derived from equity, not so much cash.
Risk and longevityUsually highly stable, less risk for the company to go under.As a service business, agencies are inherently risky in that they depend on a continuous stream of clients.Not many startups survive beyond their first year, and many don’t turn in a profit.
StructureUsually highly structured, defined processes, much slower than a startup.Depends on the agency, newer agencies typically don’t have as much structure.Usually no structure, the primary focus is on getting the company off the ground.
You’ll learnSpecialized individual contributor skills with an opportunity to get into design management.Similar to the big company, you’ll develop specialized craft skills, and you may also choose to advance in the client-relationship track.You’ll wear multiple hats and may cross over domains (marketing, front-end, and so on). If the company grows and starts hiring, there may also be an opportunity to manage incoming designers.

Big Companies

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Designing Consumer or Enterprise Products

If you’re going in-house, two more factors to consider are enterprise or consumer. If you’re going the agency route, most specialize in consumer products, but some exclusively focus on complex enterprise apps.

Table: Consumer versus Enterprise

NameConsumer companyEnterprise company
Places a premium onSimplicity, high polish, solid craft, aesthetics.Solving for complex interactions, extensibility.
Who do these companies serve?Usually many every-day individual consumers.Usually fewer buyers, who get the product on behalf of a company.
Watch out forFlurry of activity that leads nowhere.Sales-driven culture that doesn’t value design’s input.
Update cycleTypically moves faster with limitations driven by platforms (for example, mobile slightly behind web).Slower, sometimes determined by sales cycles or mandated updates that happen a few times a year.

Consumer Companies

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Designing for Platforms and Devices

Over the last two decades the world of product design and its potential applications has exploded. Previously, desktop computers, slow connections, and basic-feature phones used to dominate the digital landscape. Now with more powerful computers and ubiquitous connectivity, new platforms have emerged on the scene. Mobile is no longer the hot new trend but is a mainstream, mature platform with guidelines that have been refined over time. Emerging platforms like virtual or augmented reality are not brand-new either, but the best practices for them are still evolving.

So what does this all mean for design? In part, it depends on where you want to take your career. Working on a mature platform will offer you a safe space to leverage existing patterns and to quickly shape new features that can help solve user and business problems. Emerging platforms, on the other hand, offer an exciting opportunity to define and pioneer the space since there are no set best practices and standards yet.

Table: Mature versus Emerging Platforms

Mature platformsEmerging platforms
ExamplesWeb, mobile.Virtual reality, augmented reality, wearables, autonomous vehicles.
Design patternsEstablished and concrete, evolving slowly.Fluid and changing, opportunity to pioneer and set the precent.
Risk levelNone, these platforms are here to stay.High, these platforms may not be the right solution or may not be economically feasible.
AdoptionHigh across enterprise and consumer markets.Varies, for example, the use of autonomous vehicles is restricted to certain regions.
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Company Location and Surrounding Ecosystem

In today’s largely digitized world, the physical environment still matters to a degree. Living in a city that has a vibrant tech ecosystem confers a number of advantages. Take for example the San Francisco Bay Area. The venture capital industry creates an opportunity for many new companies to kick start growing. A few of these companies go public and become your regular big high-tech company like Google or Facebook, thus creating even more opportunity. Even in the case for startups that don’t make it, and that’s usually the case for many of them, the ecosystem makes it easier for employees to transition to another company. Because tech opportunities are abundant, the risk of being unemployed for a long period of time is significantly less compared to places that don’t have a tech ecosystem.

Aside from employment opportunities, there’s a higher chance to run into other like-minded folks and to strike new connections. San Francisco, for instance, has no shortage of tech- and design-related events happening every day. Every summer, San Francisco Design Week allows companies to open up their doors, giving eager designers a sneak peek into the space. Aside from connecting with other designers, there are courses and training for product managers, bootcamps for new engineers, and overall a vibrant ecosystem that supports professional development.

story When I first moved to San Francisco, I found one of my jobs by waiting in line for a product management event. Outside the venue, in the uncharacteristic San Francisco rain, I struck up a conversation with a couple of folks behind me. One of them happened to be a data scientist who was looking for a designer for her startup. I applied and a few months later got the job. This is the power of serendipitous connections and being in the right place at the right time.

Of course the Bay Area is a well-known place, but it does have its challenges, such as rising costs of living that promotes a transient population, making the Bay less of a destination and more of a spring board. According to Hired’s 2018 report in the U.S.: Seattle, Austin, and Denver are some of the top cities for relocation for tech workers. New York City boasts its own tech hub, while having far more diversity than the Bay Area. Boston’s high student population and medical focus create a unique culture of health tech innovation.

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Remote Work and Location

In the times of COVID-19 many companies are now going remote. Some, like Facebook, Twitter, and Coinbase allow employees to permanently work from home. While not all companies are following this trend yet, it’s highly likely that in the future more opportunities will be geographically distributed.

If you are interviewing for a remote role, it’s important to dig into the details of the remote arrangement. Has the company done remote work before, or is this a first-time experiment? It’s not necessarily a red flag if you’re the first remote employee. That said, you should learn more about how the company will support you if you are the sole remote pioneer. Holloway’s guide on Remote Work is a good resource for anyone figuring out how to navigate the remote work experience.

Considering Industry Specialization as a Designer

One decision to consider when you’re looking for your next job is whether you want to specialize in a particular industry or domain. For example, you may want to specialize in the healthcare sector because you think that’s an area where you’ll make the most impact and you may already have some prior industry knowledge that can put you at an advantage. As an industry specialist, you’ll be able to get up to speed quickly on new projects and command a premium for your salary. Typically designers choose to specialize later in their careers, but there is no right approach as it’s largely a personal choice.

You can also consider remaining an industry generalist. This may be a good choice when you’re not yet sure if there’s a particular industry you want to focus on and if you still want to double down on your design skills. Your lack of context sometimes may also be an advantage as it may lead to breakthrough solutions that a specialist may have missed.

Specializing in an Industry

As a designer specializing in an industry, you’ll understand the domain deeply and will be able to make a faster impact to the company that hired you. If you’re coming to the design from another role (education, for instance), this could be a good way to get an in. For example, new designers who have worked in your field (let’s say as a nurse practitioner) will have a domain knowledge advantage over designers who have never done work in this space.

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Design Impact, Ethics, and Diversity

Problems Worth Solving

As you’re considering companies and opportunities, it’s helpful to also to step back and think about the type of impact you may want to create and the legacy to leave behind. Are you more comfortable working on a deep problem that impacts few but has the power to change their experience significantly? Or would you prefer to cover a smaller problem that affects millions? There isn’t a right or wrong answer here, and just like the question of different cultures—some of these problems may resonate closer with you than others.

When we make decisions, we’re usually well aware of our present surroundings and our current situation. While usually it’s good to be present in the moment, sometimes it may deter us from taking on an opportunity that might seem risky in the near-term. One way to get over this risk is to reflect on this experience as if you’re looking back at it. Jeff Bezos calls it the regret minimization framework—if you were to look back in your life as if you’re 80 years old, how would this experience feel? Sometimes this additional perspective can help us see things in focus when viewed from a broader lens.

But First, Do No Harm

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Mapping Your Design Futures3 links

Now that you’re familiar with the job criteria, take a step back to brainstorm what aspects of that criteria are important to you. You can use this job evaluation template to get started. One way to think about your next role is in the context of your previous positions. What lessons did you learn there? What was useful and what wasn’t as useful? What do you want to do more or less of?

Mapping your design futures

Envisioning Different Futures

When we think of career paths we might think of a linear, incremental line steadily progressing as we’re improving a little bit every day. But oftentimes progress is not linear. Sometimes you hit a plateau and stagnate, other times you break through and grow fast. Imagine how your design career and your life can unfold in the next five years. You can look at this from a couple of perspectives.

Here are a few futures to experiment with:

  1. What would your future look like given the current trajectory and if you stayed in the role that you’re currently in over the next few years?

  2. What if you specialized in a specific domain, for example healthcare or e-commerce design, over the next few years? What would your path look like?

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Additional Resources

If you want to learn more about applying design thinking to your life, take a look at Designing Your Life: How to Build a Well-Lived, Joyful Life, by Bill Burnett and Dave Evans. If you’re interested more in futures thinking, check out What the Foresight, by Alida Draudt and Julia Rose West. We commonly think about the future on a linear scale, where things improve gradually over time. This book challenges this notion by introducing multiple futures.

Part II: Taking Action and Finding Opportunities

Shaping Your Identity15 minutes, 8 links

Before diving into portfolio case studies it’s important to step back and think about the type of design prowess that you bring.

Uncover Your Superpowers

Product designer is a generic title. In companies like Facebook, regardless of seniority, everyone is a product designer and so it’s hard to understand who is senior, which level they’re at, or even what their strengths and weaknesses are. That’s why it’s important to define the type of product designer you are—one way to do so is by highlighting your own superpowers.

When we typically think of superpowers, the first thing that usually comes to mind is the mastery of a specific skill. Obviously this superpower should be highlighted, but don’t worry if you’re not there yet or if you can’t point to one skill that’s excellent.

What skills do you have that are above average? What work using those skills are you proud of? It could be something as simple as rough illustrations and storytelling. What missing skills or perspectives can you bring to a team? What’s your unique point of view? What unique experience do you have based on your previous roles?

Transferable Skills as Superpowers

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Beyond Skills—Show Personality

You are more than a collection of skills. When you start interviewing with employers, they also want to see who you are as a person—after all, they’ll be with you and you’ll be with them for eight-plus hours each workday. Now this might seem a bit like you’re revealing too much, or maybe you’d rather be a chameleon and blend in with the environment to fit in. Don’t.

In addition to your skills, you’re hired for your opinion—your views and your unique perspective that you’ve been honing all your life. Of course, there’s a subtle art to showing your personality strategically, as you don’t want to go overboard by revealing everything all at once. Focus on things that are unique, relevant, and that people can relate to.

As part of my portfolio I would sometimes include photos of dishes I made in the past to tell a more compelling story of cooking and design:

Figure: Food as Portfolio Work

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Write Your Pitch

Great! Now you have your superpowers and you have highlights of your personality. Next, put it together in an easy-to-consume narrative. If a stranger met you today, how would you introduce yourself? What impression do you want to leave behind?

By drafting a couple of versions of your statement, you’ll get a better sense of the narrative you want to convey and will have a response at the ready when you’re responding to emails or hitting up networking events.

As with uncovering your superpowers—don’t be afraid to step away and ask for help. If you were to ask a friend or a co-worker, how would they describe you or pitch you? What would they say? Try this exercise with others or a group of friends—you might discover new qualities or some that you’ve taken for granted that others find valuable in you.

Figure: Designer Bio Generator

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Update Your Resumé

Before diving into the portfolio, start with your resume or LinkedIn. When someone will be looking over your profile, they’ll want to understand your story and have the right context when looking through your work. A lot of these initial impressions are based on quick scans of your profile.

  • Where are you coming from?

  • What have you done in the past?

  • What impact were you able to deliver?

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Building Your Portfolio42 minutes, 12 links

Portfolios are a prerequisite for a design role these days. Just like with design exercises, sometimes industry experts also bemoan this point—what if the designer is too busy to make one? What if the portfolio is out of date? It’s rare to get an interview without a portfolio, and even if you might get to a phone screen, you’ll still be expected to present your work during the final interview. But building a portfolio needn’t be a painful process.

You want to build two portfolios:

  1. Your online portfolio. This may be private; you’ll share it as part of your application. Your number one goal with this portfolio is to land the phone screen. It should pique your viewer’s interest without revealing too much info (you’ll talk about that during your on-site).

  2. Your on-site portfolio. When you get to the final interview stage, you’ll need to create another portfolio. This one will be less verbal and more visual. You’ll typically present one or two projects in depth and may have additional slides in an appendix to go over details. The goal of this portfolio is to make a winning impression and get an offer.

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What If You’re Fresh Out of School?

One of the common challenges that new designers face when putting together their portfolio for the first time is the lack of so-called real-world design projects. If you’ve just completed a bootcamp or graduated from an undergrad or graduate program, you may not have a lot of working experience. By all means, if in your school projects you worked with a client—a startup or a large company—be sure to feature that work, including any internships that you’ve done. But if you have none of these?

Hiring managers, especially those without a design background, sometimes don’t give as much weight to candidates who don’t have many real-world projects in their portfolio. Sometimes they see it as a risk to take on an entry-level candidate, thinking that they’ll have to spend a significant amount of time training and developing the employee.

story In a recent interview, a founder mentioned to me how he was afraid of hiring junior designers: “Yeah, we’ll get them in, they’ll do exactly what they’re told, and that will be a complete failure. What we need is people who can push back and tell us we’re wrong and come up with a better solution than we would have on our own.” So don’t be afraid to showcase your process and frameworks that you’ve used to push back on problems to come up with better solutions. As designers, redefining problems is our core competency—no matter the seniority.

So if you find yourself in this situation, what can you do? Generally, you can take a couple of approaches, and my recommendation is to experiment with some of these while you’re still applying to your dream role.

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Consider Your Portfolio Personas

The main goal of your online portfolio is to land the phone screen. It is not to be exhaustive in describing the rigor of your process (save that for the on-site!) but rather to start the initial conversation and continue the momentum from online, to phone screen, to an on-site interview.

Be choosy in what you show here and focus on curating the best representative image of your work. Because you will not present this portfolio, your portfolio must stand on its own when a recruiter or a hiring manager is looking through it.

Recruiter

A recruiter’s job is to source qualified candidates and to present them to the hiring manager. Good recruiters understand the design process, have worked with other designers before, and know what a hiring manager needs. Since their job is to get many qualified leads in the pipeline, they’ll be scanning your portfolio and resume for signs of good work and process.

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Gather Your Content

Before you begin your portfolio, it helps to have everything all in one place. It’s common industry advice to “build your portfolio before you need it.” But let’s face it, free time can be hard to come by, and spending it on building a portfolio doesn’t feel like it’s time well spent. So my recommendation is to go an easier route and to develop the habit of capturing your work as it unfolds.

important To make portfolios, build the habit of capturing key screenshots or changes in your work throughout the process.

A portfolio project often tells a compelling story of design execution from beginning to end. Having artifacts of the experience will help you substantiate your story and provide the evidence you need to come across as an expert in your craft.

Figure: Collecting Artifacts of Your Process

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Portfolio Formats to Consider

These days, portfolios can take on many different formats. In the past, designers would create a customer site with six thumbnails for each portfolio project. Now there are more options to choose from. Remember, the goal of your online portfolio is to get a phone interview. During that interview you’ll do a light portfolio review with a hiring manager and the recruiter, so you want to show work that you’re proud of and that’s relevant to the job at hand.

Once you’re in the final rounds, you’ll have to create a different portfolio that’s specifically tailored to the company and the presentation format. So don’t spend so much time on building your online portfolio that you don’t submit it anywhere.

Table: Portfolio Format Comparison

TypeBenefitsWatch out forLearning Curve
Note-taking app (like Notion)No technical knowledge to get started.Navigation and organization of your case studies. Don’t get stuck writing a book that has no visuals to tell your story.None. You’ll need to understand some basic mechanics of linking pages together, but it’s a small time investment.
Deck (like Keynote, Figma, or Google Slides)A deck helps you optimize for the right balance of content and visual while building interest.By default, decks aren’t as accessible on smaller devices like phones.Some learning curve, as you may need to know the ins and outs of deck design and the app to get a good handle on your presentation.
Site building app (like Webflow)Fastest way to get started with ability to customize and make changes rapidly as you go.Over-indexing on layout and site design while not having strong case study content.Some learning curve, but not as difficult as learning front-end development from scratch.
Your own siteUltimate freedom and control; you can structure your content however you see fit.Debugging your portfolio. You may also get unfairly judged if your site is broken.High learning curve if you’re starting out or if you’re brushing up on the latest CSS/HTML.
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Organize Your Portfolio

Design portfolios can feel like never-ending work. Sometimes we avoid the effort altogether in favor of “research.” We go online, we look at other designer portfolios, and maybe even get a little intimidated by some of the work out there. Can my portfolio be just as good?

Other times we dive right into design, skipping the important writing process altogether. Or we agonize about the content so much that we write a book, only to discover nobody wants to read it online.

A solid portfolio can be hard to pull off. We’ll take a look at what a hiring manager looks for in a portfolio and note how to avoid mistakes. I’ll use a deck format (via folio—a free portfolio template deck that I’ve created) to illustrate these examples, but rest assured you can adapt and use any portfolio format as long as it communicates these key ideas.

You’ll want to address these things in your portfolio:

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Prototype Your Portfolio

If you really want to maximize your chances, prototype your portfolio before submitting. You only get one shot when it comes to making a first impression, so make it your best one.

Playing Hiring Manager

Is there a dream job you have in mind? Print out the job description, then hand it to your friend and let them play the role of the hiring manager. As they go through your work, ask them to speak out loud. Seeing their gut reaction to your portfolio in person, as they’re voicing what they see, is powerful.

If you have industry contacts, reach out to designers or design managers and get their feedback. Managers usually look at portfolios regularly, and designers, too, may sit on interviews, so they know what to expect.

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Promote Your Portfolio

As we talked about earlier, generally it helps to be very tailored and specific with your job search and your portfolio as well. But if you’ve already done the work, if you’ve created and organized your case studies, then you should also consider promoting your work in other places. Think about your online site as a landing hub—a place where you have fine control over what to show. Within this hub you have content about yourself, your curated work in the form of a portfolio, as well as any other side projects you’re working on that make you stand out.

Figure: Your Online Portfolio Is a Hub

Your online portfolio is a hub

Your online portfolio as a landing hub.

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Applying for Roles37 minutes, 15 links

What’s the one unfair secret way of getting your foot in the door when applying to jobs? Easy. Connect with people first. The best strategy is not to cast a wide net by applying everywhere but to be focused on the few opportunities where you can make an outsize impact. Your future employer appreciates this effort too—they’d rather hire someone with the necessary skills, with a passion for the company’s mission, and who has done their homework over someone who’s just looking for whatever they can get.

When you are applying, your best bet is to use a variety of channels, from reaching out to alumni to promoting your portfolio in other channels. All of these will help you raise visibility and increase your chances. However, these tactics won’t be as effective if you haven’t figured out the strategy first—understanding how your skills fit with the types of jobs you’re looking for.

Two Strategies for Applying

Broadly speaking you can apply to jobs in two ways: casting a wide net by applying to several dozen companies or targeting your search to companies and roles that fit your skills and needs best.

Casting a Wide Net

By casting a wide net you can reach out to several dozen companies in a short amount of time. Unfortunately, that means you’re right there in the sea of resumes and portfolios, with a lower chance of standing out. You’ll get some responses, but the rate will be in the low single digits.

Even if you do get a response, it’s hard to tell if the role is a good fit for you. When you’re desperate, it might feel like anything that looks decent enough is a good fit, but it might not be the right opportunity for you, leading to frustration when you actually start working there.

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Using Referrals

One effective way to apply to jobs is through an employee referral. With a contact inside the company, you shortcut the tedious part of the process and your portfolio lands squarely right in front of the eyes of a recruiter or a hiring manager. How you ask for a referral makes all the difference.

Getting Referred by People You Worked with Before

The best referrals come from people you’ve developed a strong relationship with by working together. Think of these folks as people in your tight-knit inner circle. These are the folks that not only can get you in the door but write a glowing review so that the interview completely flips. Instead of selling yourself, they work hard to get you in and sell the opportunity to you.

However, these are not the only referrals to act on. As a designer you’re uniquely positioned to interact with people cross-functionally. This means right out of the gate you have a broad and diverse network of folks that you’ve worked with before, such as:

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Reaching Out Directly

The best way to connect with a company is by reaching out directly. Whether it’s identifying the hiring manager or the recruiter, you want to initiate the conversation and start there as opposed to submitting your portfolio online and hoping for the best.

Yes, this approach does take work and it won’t be easy. You may need to ask around and reach out to a couple of folks before finally reaching the hiring manager, for instance. However, because it’s not easy, most people won’t take this route. So this is yet another way for you to differentiate yourself and reinforce the trait of taking action and being proactive.

Talking with the Hiring Manager or Recruiter

If you know the hiring manager for the role, reach out to them directly with your application. If you don’t know the manager or who’s doing the recruiting, look them up. This will be harder for larger companies, but for startups or mid-size companies, usually you can poke around their site, LinkedIn, or AngelList to at least find the recruiter who posted the listing.

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Working with Recruiters

Recruiters come in all shapes and sizes. To simplify things, I’m going to focus on in-house and recruiting agency recruiters. This model is not unlike that for designers. In-house recruiters have a deep understanding of the company and are sometimes embedded on the teams they’re hiring for (design or engineering, for example). Agency recruiters work with multiple companies and bring the advantage of breadth—potentially placing you in a company that’s a great fit for your (and their) needs.

In-House Recruiters

In-house recruiters are usually your first point of contact when it comes to getting the lowdown on the company, the team, and the job itself. A good recruiter will do their best to answer your questions and make sure you’re left with a good impression (even if you might not be the right fit just now). Use them as a resource to understand the role.

important Recruiters can be your best ally. Treat them well. Focus on high-quality recruiters—equip them to succeed and they’ll in turn help you.

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Reaching Out to Alumni

If you went to college, you have an alumni network. Universities usually do an adequate job at keeping records on their alumni—after all, who else are they going to call for more donations, though in my experience, they don’t do a good job of promoting these resources to the alumni themselves. Most of the time they do exist, so it just takes a bit of time to search for them on your alma mater’s website.

As an alum, you’ve paid a ton of money to go to school, so make sure you get the most out of your investment.

Here are some resources your school might have:

  • Official local alumni events in your area, or see if you can find your local event organizers to potentially organize an event together.

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Here are some low-effort online strategies to help you land the first interview. Using a blend of different methods, both offline and online, will help maximize your chances of landing the phone screen.

Make Companies Apply to You

What if instead of applying to companies, the companies applied to you? Reverse job auction sites flip the traditional model of filling out the same form repeatedly for different companies. Instead you submit one candidate profile and companies bid on your profile over several rounds.

Although you won’t find the giants like Facebook or Google here, the caliber of tech companies is high. You’ll get outreach from smaller startups and mid-size companies, as well as larger and more mature organizations like big consulting companies that are building up their design teams.

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Waiting Proactively

When you’ve applied to jobs, there’s often a delay on the other side in getting back to you. The hiring manager may be busy, reviewing other applications, or gone on vacation. That said, when you’re looking for work while unemployed, every day counts. Believe it or not, you have more control over the situation. You can either continue applying to more places, or follow up with places you’ve applied to.

Since we already covered various strategies for the former, we’ll focus primarily on the latter half—the follow-up. A big part of getting the first (phone) interview is figuring out what’s happening on the other side. Did they get your application? Is the job still open?

You can get to an answer by proactively reaching out to the employer:

  1. Send a personalized email. Reiterate your interest and let them know about your application.

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Networking Authentically16 minutes, 17 links

Think of networking as another powerful tool in your job-searching arsenal. Aside from the short-term benefit of finding a job by networking, it opens up the possibilities of making mutually beneficial long-term connections that can last over the course of one’s career.

Figure: Discover New Ideas and People at Events

Discover new ideas and people at events

Events are great for exposing you to new ideas and people.

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Networking During a Pandemic

new With COVID-19, the rules of networking have shifted. More events take place remotely, so the opportunities for a casual chat before an event are going away. But in some way, it’s also an opportunity to connect with the person you’re interested in talking with after the event is over. Reaching out to them via email or a LinkedIn invite and letting them know that you’ve both attended an event recently can help you establish common ground in addition to the topic.

Figure: Remote Conferences

Remote conferences

In 2020 the biggest design conferences and events primarily took place online. Adobe Max streamed hundreds of sessions across the globe from the US, Europe and Asia. Who knows, remote-only conferences might be the future.

Tips on Talking with Strangers

You might not feel like going out there because you’re not an extrovert and prefer not to be the life of the party. That’s OK. It’s a common myth about networking that you need to get out there, shake hands, and hand out business cards left and right while jumping from one person to the next.

When I first started going to design events I usually froze, latched onto the first person that I met, and kept talking to them as if they were my lifeline. But over time, by attending many events, networking has become more natural. Today, I still enjoy spending my time alone, but going out is no longer a fear-inducing activity—it’s fun to meet new folks and find ways to give back.

At its core, networking is about finding mutually beneficial ways to help each other. If you’re new to it, here are some things you can do. If you’ve gone to events before, feel free to skip.

  1. Don’t be afraid to be the first one to strike up a conversation. You can start by asking what brought them to the event? What are they hoping to learn? Have they attended similar events?

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Deciding on a Conference

If there aren’t many events in your part of town, see if you can attend a conference that brings design professionals together, ideally for a couple of days so that you can make a couple of high-quality connections. There’s no shortage of conference lists these days and, with talks now going remotely, attending is easier than before—no need to figure out the logistics of scheduling flights, hotels, and transportation to the venue.

Organizers and Topics

Before going, it helps to familiarize yourself with the conference itself. What’s the theme? Who are the organizers? Have they done this conference before, and how were those (you can usually find reviews online). Next, look at who’s going to be speaking and what their credentials are. Based on this info, start comparing conferences and earmarking the ones that look good.

important Aside from looking at the speakers and companies that are attending, take a close look at the schedule. One major thing to watch for are the breaks between presentations. The magic happens between, not during, the talks. More breaks equal more opportunities to connect. Is this conference packed back to back with little time to spare, or is there enough time for breaks between talks? Are there also dedicated food breaks—lunch, extended coffee, and treats?

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Picking Events to Go To

Depending on where you live, the cadence of events varies. It’s usually easier to find them in larger cities. When I used to work in a suburban area, I would drive an hour to Boston just to attend some of the events there and stay close to the community. Here are a couple of things to consider when evaluating where to go.

Interest-Based Design Events

One way to choose events is based on a topic or theme. Over the years I’ve been passionate about healthcare and design and have attended multiple events in that space, from hackathons, to quantified self meetups, to design events with a focus on healthcare. Attending these types of meetups is a great way to meet people in the broader industry and especially good if you want to focus your career on a specific vertical.

Figure: Theme-Based Events Focus Deeply on a Topic

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Where to Find Events

Where can you find events? Start by searching for “design” on Eventbrite, Meetup, or even Facebook Local. It’s as simple as that.

Here are a couple of well-known organizations that are good to check out:

Connecting with Local Professional Communities

In addition to the more prominent orgs such as the ones above, you can also search for local chapters or local orgs. Usually these have more clout and can better connect you to the local community. I’ll list the ones that I know of in San Francisco, but even if the same ones don’t exist in your city, it’s possible your local organizations follow a similar format. If not, that’s something you could pitch to them (for example, organizing a portfolio review event or a mentor night).

Aside from talks, mentoring and portfolio events provide opportunities to connect with people and companies you’re interested in and improve your skill at showing the work itself.

Andi Galpern organizes the Cascade SF events. In addition to design talks, she hosts mentor nights where attendees get to show their portfolio (or ask for career advice) with up to four mentors. I’ve been mentored there and provided mentorship and can’t recommend this format enough.

Julie Stanescu runs Rethink, which hosts informative events (you can also find recorded talks online) and they pack a big crowd. Interestingly enough, Julie started Rethink when she first moved to San Francisco as a way to build a forum for design discussion and connect with great designers here. So if you find yourself in a place that has no design communities, consider bootstrapping one yourself.

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Don’t Stop at Design Events

There are many others! Once you go to an event you can ask the attendees where else they like to go. Don’t limit your events to product design though. Here are some good ones that I’ve attended in the past and found useful:

  • Products That Count. Founded by SC Moatti, in-depth events with presentations from PMs, VCs, and other big movers and shakers in industry.

  • Product School. Hosts informative events from speakers of top-tier tech companies in addition to doing PM training.

So if a product management or an interesting engineering talk comes around, consider going. Not only will you learn something new but you’ll have more opportunity to connect with folks who are potentially looking for design talent, and you won’t be competing against other designers at the event.

Get Started Now

With most events going remote this year, the opportunity to connect and attend an event is becoming easier and easier. Here’s how you can find some good ones:

  • Search for design on EventBrite, Facebook Local, and Meetup. What’s coming up?

  • Sign up for one event you’ll attend this month and go there. Post on your LinkedIn that you’ll be attending that event and you’re looking forward to meeting folks there.

  • Look for conferences. Make it a point to find one or two great conferences this year and attend. If money is an issue, reach out to the organizers and ask to help out.

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Additional Resources

Here are three books that I think are a must-read:

  • How to Win Friends and Influence People, by Dale Carnegie. The classic in the field, still just as relevant today.

  • Never Eat Alone, by Keith Ferazzi. Although it has mixed reviews, Keith does a great job of providing tips and frameworks you can use to meet people. At the heart of it is the genuine message that we’re better off connecting and sharing resources than hoarding away our contacts.

  • Networking for People Who Hate Networking, by Devora Zack. For those shy persons jumping into their first event, this is a great step-by-step guide. The book leads you through a series of exercises to make networking fun and enjoyable, especially for those of us who would actually prefer to spend our time (and eat) alone.

Part III: Preparing for Design Interviews

In this chapter we’ll dive into the various interview types that you might encounter. During the interview cycle you’ll be talking primarily with a recruiter and a hiring manager. For the final interview you’ll interact extensively with the cross-functional team—engineers, researchers, data scientists, product managers, and so on.

The same tips in the previous sections apply here as well. You want to know the role requirements well enough so that you can clearly sell the team on your candidacy. In the case of behavioral interviews this means thinking about the specific situations that can speak well to the desired requirements.

By knowing what to expect you can practice and prepare ahead of time. This will make your responses sound natural and you’ll be able to focus more on the interviewer’s questions and understand what they’re ultimately trying to ask.

Lastly, it’s likely that during this process you might encounter design exercises, such as the take-home design exercise, the whiteboard challenge, or the app critique. Since design exercises are a special type of interview, I’ve outlined them in a following chapter with a few sample solutions and practice prompts to help you get better at these types of interviews.

Preparing for the Phone Screen Interview12 minutes

Your first interview will start with a voice call where you’ll typically speak with a recruiter. This interview is usually preceded by an email—sometimes multiple emails from recruiters trying to get your attention. To be successful at this interview type, you should do your homework ahead of time, prepare your pitch, and be able to tell a compelling story demonstrating value so that you can advance to the next stage of the interview.

Screening Calls at a Glance

Design phone screens are usually short, about 15–30 minutes interviewing with one person. They give you an opportunity to present yourself, your work, and your interest in the company.

If this is your first phone conversation with the company, a recruiter will usually reach out. They’ll talk about the role, ask some questions, and will try to gauge your interest. Aside from screening, they also want to leave you excited about the opportunity. Take advantage of that by treating the recruiter as an ally in the interview process.

important Your 30-second intro should be punchy, specific, and short.

A call with the hiring manager is usually next. On occasion I also had these calls with peer designers. Either way, since both parties have domain expertise, they’ll dig deeper on your design process and case studies.

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Preparing for the Call

Before the call, review what you already have about the company, the role, and the person you’ll be talking to. Have your list of answers (based on anticipated questions) and your list of questions printed so you can take notes without getting distracted by typing noise.

During the Call

It goes without saying that you should be in a quiet room with strong cell phone reception. You might even consider getting a phone number from Google as a backup, but in that case make sure you have a strong wifi connection.

As the conversation wraps up, you’ll usually have a few minutes for questions. Your questions should be tailored to the person who’s interviewing you and the role itself. Focus on a few specific questions to open up the conversation and follow the thread from there. You can think of this as doing user research. What important questions should you ask first? What’s a deal breaker? What are some nice-to-haves to follow up with?

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Preparing for the Hiring Manager

This interview usually follows a few days after the recruiter screening call. Generally you’ll talk to a hiring manager, or occasionally another designer may field this call.

Similarly to the screening call, this interview should last about 15–30 minutes. By this time the recruiter should have relayed some of the information to the hiring manager so they’re on the same page. But you should still expect to introduce yourself and have your pitch ready, in addition to mentioning why you’re excited about this particular opportunity.

Your Design Approach and Process

The interviewer is interested to see if you have a specific process when approaching problems. What framework do you use? Is your approach rigid or flexible based on the context at hand? Are you able to bend and break the process while focusing on outcomes?

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Final Interview Preparation9 minutes, 1 link

The final interview is a big step in the process. Congrats on making it this far! This is an opportunity for you to arrive with confidence, be prepared for the unexpected, and, finally, leave your interviewers excited to work with you.

new With COVID-19, the traditional on-site or final interview is now conducted remotely. While the format is changed, many of the steps are similar. It’s important to prepare and to test out your remote interviewing setup ahead of time.

So what’s next? By now you should have received an email from the company with an interviewing schedule to help you prepare for the big day. If you haven’t received the schedule, now’s a great time to ask for it. This is a good way to communicate initiative while also properly preparing ahead of time.

Table: On-Site Schedule

TimeInterview typePresent
1 hourPortfolio presentationCross-functional team and designers
45 minutesWhiteboard exercise1–2 designers
30 minutesApp critique1–2 designers
30 minutesProduct collaborationProduct manager
30 minutesDesign collaborationDesigner
30 minutesEngineering collaborationEngineering manager or engineer
30 minutesTeam fitHiring manager
30 minutesWrap upRecruiter

Learning About Your Interviewers

After learning the schedule, now’s the opportunity to learn more about your interviewers—if this company has already invested time in getting to know you, it’s only fair that you should get to know them too. Start with LinkedIn and look at each interviewer’s profile: their experience, common connections, and recent posts. Look for their other online social networks or sites where they were mentioned or shared their work. If you’re applying to a startup or a smaller company, be sure to research the leadership team too.

This info will be useful during the interview itself, as it will help you:

  • Anticipate types of questions you’ll get asked.

  • Address potential concerns relevant to portfolio pieces.

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Creating Your Own On-Site Packet

My deliverable at this stage is an on-site packet composed of:

  • Summary page. This has the name of the company, schedule, street address, and point person for the interview and their phone number, in case I need to call when I arrive or get lost.

  • Pages for each interviewing event. Covers any interesting facts and questions I want to follow up with for each person.

  • Extra pages. Just in case, for note-taking during interviews.

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Day of the On-Site

For your on-site, it’s important to have the basics covered. That means eating well a few hours before and getting proper rest. Think of this as a test. You have the knowledge and skills, now it’s important to demonstrate your major skills and accomplishments in one go.

Gather Your Belongings

If this is a full or a half day of interviews, it will probably be demanding, so be sure to bring your:

  • laptop (even if you’re presenting on an iPad, have it as a backup) with a charger

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Presenting Your Portfolio: Crafting a Compelling Story14 minutes, 3 links

As part of your final interview you’ll be asked to present your portfolio. Out of all interviews, this one is priority number one. See this as an opportunity to show the great work that you’ve done, reinforcing the fact that you can do it and more again.

important The in-person portfolio is different from your online portfolio, which the interviewers have already seen. This is an opportunity to feature one to three best projects and go in-depth on how you’ve achieved and exceeded objectives given the constraints.

Here’s how you can create a gripping narrative that gets your interviewers excited to work with you.

How Your Portfolio Will Be Evaluated

Your portfolio presentation will be evaluated from multiple angles. The criteria here are broader than the design exercise since you’ll be showing work you’ve done as part of a team. Your interviewers will be interested in seeing the following:

  • Problem scope. How complex were the problems you were addressing? This in part determines your seniority—did you lead multiple projects in parallel, with ambiguous goals, across various channels?

  • Collaboration. How did you work with your team? What conflict did you encounter and how was it resolved? Were you able to inspire and bring out the best in your teammates?

  • Adaptability. What approaches did you try? What failed and how did you iterate on the process to keep things moving?

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Your Audience

A variety of folks will see your presentation, each with a different focus:

  • Design manager. Craft skills, quality, process, and style.

  • Product manager. Prioritization, business outcomes, impact.

  • Engineering. Productive collaboration with engineering.

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Building Your Deck

The number one person you’re building this deck for is yourself. You’ll want to create a modular portfolio that you can remix at a moment’s notice if you’re called in for an interview with another company. To help you get there, I recommend you start an assessment of your recent work.

Stacking Your Projects

What were your recent projects that you consider to be your best work that show a variety of skills? Highlight projects that played to your unique identity as a designer—your combination of skills, point of view, and process that led to a result no other designer could have achieved.

One way to put together a project stack is to evaluate each project individually on your craft skills, such as user research, interaction design, visual design, and affected platforms.

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Storytelling for Success

To make an impactful presentation, turn it into a story. You’re the hero of your own script. What trials on your path gave way to triumphs? Let’s break this down into three parts: presentation, project, and process.

Figure: Presentation, Projects, and Process

Presentation, projects, and process

The majority of your presentation will be spent on process, but don’t skip context.

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Portfolio Presentation: Public Speaking Tips14 minutes

Amplify your message and engage your audience. Your speech will be part script, part improv. Here we’ll cover presentation basics from where to sit to how to end on a high note. These days many companies are shifting in-person portfolios to online conference calls. While the context is different, many of the same tips still apply.

Your Content on a Silver Platter

Think about the last time you went out to a restaurant. What did you order? Where did you eat? If it was a high-end restaurant—the light (or the lack thereof), the ambience, the music, and the way your dish was presented all played into a delectable experience at first bite.

Now think of the time you got a similar dish for takeout. Most likely it came in cheap, disposable packaging. The food might have come in different packets that you had to mix yourself. Same basic ingredients—completely different experience. The way you frame your presentation is the difference between fast food and fine dining.

Setting up the Environment to Your Advantage

Aside from getting the following basics covered, remember, this is your time to shine, not shy away. Carry a leadership mindset with an executive presence to your on-site interview. The goal is to tell your story, show the work, and connect with your audience.

Practicing ahead of time by yourself or with your friends will make a big difference. If you really want to get into it, I recommend joining a local public speaking group or taking an improv class. Both will give you structure and frameworks for scripted or spontaneous scenarios.

Build Rapport While Setting Up

Hopefully before you start your presentation, you’ll have time to set up your laptop and project on screen. But if you walk into a room full of expecting looks, fear not, now’s the time to say hello and ask questions about how to get your laptop to project with whatever setup they have. This usually takes a while, so get ready to troubleshoot.

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Setting up Your Remote Environment to Your Advantage

With COVID-19 taking most interviews from on-site to remote, it helps to set up your space in advance and to get familiar with the conferencing software.

Presenting with Multiple Screens

Depending on how your home setup works, you may have one or two extra monitors in addition to your laptop. Usually the laptop will have a camera but the displays will not. Since you’ll want to face your interviewers, my recommendation is to project your presentation on your display in front of you, while having your presentation notes (if you’re presenting in a note-style format) in front of you on the laptop.

Camera Setup

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Speaking Tips for Success

Now that you have all the technical hurdles behind you, it’s time to dive in. One way to kick off is to let the people in the room introduce themselves first. This allows for a nice segue into your own intro via the presentation deck.

Your intro is your unique frame of your identity as a designer. Use this opportunity to weave a story about your education, background, interests, and your unique perspective, ending with why you’re excited to be interviewing with the company today.

As an interviewer evaluating a candidate—this intro is critical. You want to confidently communicate your story to send a clear signal to interviewers that you’re deliberate and intentional in your career path. Don’t shy away from revealing relevant hobbies; this is an opportunity for you to come across as a whole person, not just as a designer who consumes coffee and produces pixels. As an interviewer I want to know what makes you tick, what are your strong areas, and what aspects of design excite you the most.

As I mentioned, if you’re really interested in getting better at presenting, I recommend taking a public speaking workshop. Many years ago I signed up with Toastmasters, a public speaking club that would meet weekly. The basic course alone was inexpensive and provided a good step-by-step foundation to practice various speech techniques in a safe space.

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Practice, Practice, Practice

When you’re heads down, operating on your presentation, it’s hard to step back and do a practice run. I get it. But I do hope that this will encourage you to think hard about how you frame your message, not just what you choose to present. Ultimately, a combination of strong content and engaging presentation will lead to a memorable experience in the eyes of your audience that will separate you from other designers.

important If you give speeches regularly (and most folks don’t) then you can get away with less practice. But if you don’t and are feeling rusty, a general rule of thumb is to spend about ten times as much time practicing a speech as giving it. Now this might seem like a lot—a one-hour presentation would equate to ten hours. But if you’re presenting your portfolio to multiple companies and you’re interviewing in several places, this number becomes much more reasonable.

Behavioral Design Interviews19 minutes, 2 links

Behavioral interviews usually follow soon after your design presentation and the various design exercises. I’ll break this interview format down by function: outside of design, you’ll learn how to build rapport with product management, engineering, and research. You’ll want to build rapport and get people excited to work with you. I’ll also share best practices with stories of success and failures along the way.

Behavioral Interview Format at a Glance

The goal of cross-functional interviews is to get a 360-degree view of how you approach your work and collaborate with others. Typically these will be one-on-one interviews about 30 minutes each or one-hour pair interviews.

If you’re applying for an in-house role (either at a startup or a large company), you’ll talk with cross-functional peers in product and engineering. You might also have a researcher or a data scientist sit in. For agency roles, you’ll be primarily speaking with designers.

The best way to prepare for your final interview is by actively working with your recruiter. Find out what to expect, the schedule, and the people you’ll be speaking with. Lastly, many companies are starting to do behavioral interviews over the phone or a video conference. While the format is different, many of the same principles apply.

important When you’re presenting your portfolio, you usually get into the details of the situation and provide specific examples because no projects are alike. Same with behavioral interviews—get specific and answer the question succinctly. Aim to respond to the question in about two to three minutes. Hypothetical responses that err on how one should or in theory might do things aren’t good responses as they don’t give the interviewer a clear signal of how you actually handled things in the past.

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Peer Design Interview

Usually, right after your portfolio presentation you’ll be slated for a peer design interview. If that’s the case, expect some detailed follow-up questions on your work. They’ll also dig into:

  • Your past experience. Anything that was mentioned in your portfolio, resume, LinkedIn, and so on.

  • Design collaboration. How you work with other designers.

  • Your working style. Preferences in process and your approach to work.

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Hiring Manager Interview

Most of the time the hiring manager for a design role will come from a design background, but in smaller startups they might be an engineer or a PM looking to establish a design team. Depending on who you get, the questions will vary slightly but the objectives are similar.

Usually you’ll talk to them at the end—by this time the other interviewers have submitted feedback or flagged additional things to probe on. In addition to these, the hiring manager will try to assess your:

  • Professionalism. How you carry yourself and how you come across.

  • Career aspirations. Where do you expect to be in the next few years.

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Cross-Functional Interviews

After interviewing with the designers, you’ll talk with your cross-functional peers: product managers, engineers, and researchers. The primary goal of these interviews is to understand how well you work with others and measure your level of empathy and consideration of others.

Product Manager

In many cross-functional teams, you’ll work with the PM closely on a daily basis. They’ll want to know:

  • How you’ve worked with PMs and any conflicts you’ve encountered.

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Behavioral Interview Tips

Even when you have your answers prepared, your delivery still matters. Here are a few best practices to consider.

Use a Story Format

Many behavioral interviews will ask you about a situation in the past to assess how you handled it. It’s not unlike the methods we use in user research. We don’t ask participants to predict what they’ll do in the future—we ask them what they actually did. In an interview setting, you’ll also have to get specific and use your storytelling skills to give an example and provide concrete learnings.

As an example, here’s how the structure might look like when you’re asked “Tell me about a time when your design failed”:

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Additional Resources

If you’re applying to a large company, it’s highly likely that some of those questions have already been documented somewhere. These questions may not be as easy to find for smaller startups but it helps to look around. You should consider using resources such as LinkedIn and Glassdoor. Note, these questions will change so don’t expect the exact question in your interview, instead treat these questions as practice.

Part IV: Acing Design Exercises

Design exercises are one of the most controversial interview types and are not without fault. It’s not uncommon for many designers to bemoan them, and with good reason. These interviews sometimes inadvertently screen high-quality candidates out. After all, not everyone can dedicate hours outside of work on a take-home design exercise. Sometimes the criteria for success can be confusing for interview candidates, and this is often exacerbated by the people who are conducting the interview when they don’t have a clear idea of what they’re looking for.

So why do companies do them?

The short of it is that design has become a competitive landscape with many candidates applying for design jobs. A portfolio, the strongest indicator of one’s skill as a designer, sometimes doesn’t tell the full story. Usually most design projects are team projects, so it can be hard to tell who did which part. So when you are presenting your portfolio, be sure to reinforce the role that you’ve played and the specific work that you’ve done.

For certain companies—those who cannot afford a design manager or who may just need a strong individual contributor from the outset—they may not know exactly what to look for. They frequently see designers as having nontransferable skills between industries; for example, if you worked in design for enterprise products, you may not flourish at a fast-paced startup. These are just some of the common misconceptions that you may encounter at a company that has a low design maturity.

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The Take-Home Design Exercise9 minutes, 1 link

As I mentioned previously, design exercises are not without fault, and as a candidate you always have a choice whether or not to accept one. Sometimes companies allow you to swap one design exercise for another—for example, instead of the take-home exercise, doing a whiteboard challenge.

Or you can choose to forego the design exercise altogether and end the interview—sometimes this is an option if you’re interviewing at other places and this one isn’t worth your time, and they’re not budging on pushing back the timeline.

caution Beware of companies that try to get free work out of you via a design exercise. The design exercise should be different from their business and the deliverable shouldn’t be a fully coded concept that can be implemented. That said, the companies who have challenges that are similar to their business aren’t necessarily trying to get free work out of you. Sometimes they don’t know how to evaluate designers and therefore they create a challenge similar to their business because they’re the domain experts.

At the end of the day if you have concerns or suggestions—these are all great points to bring up with you recruiter. Try to better understand why the company is doing a take home exercise and what they’re trying to achieve. Some companies are also starting to compensate their candidates for the design challenge thus making this interview type a little more palatable.

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Design Exercise Format and Criteria

Typically, candidates are given a few days to a week to complete the take-home assignment. Usually recruiters warn candidates not to spend more than “a few hours on it,” but in reality many candidates spend a fairly significant amount of time. After all, if you really want to differentiate yourself, you have to put in the work.

So you’ve got a design exercise on your hands and the clock is ticking. To make sure your solution is adequate, you’ll need to make sure you understand the evaluation criteria. Every company will vary, but typically they look for:

  1. Process. How you approach and solve ambiguous problems.

  2. Craft. Strong interaction design and visual design work delivered in a short amount of time.

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Nine Principles for a Successful Design Exercise

There are no shortcuts, but you can increase your chances by:

  1. Practicing. If you’ve never done a design exercise, practice by finding a problem you’re interested in. Give yourself a deadline, write a prompt, do it in the allotted time, and give yourself an objective evaluation.

  2. Understanding context and questions. Get to know the constraints and how your work will be evaluated.

  3. Going above and beyond. After understanding the baseline requirements, see how you can exceed expectations. As Paul Graham says, “The best protection is always working on hard problems.”

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Start with Context

OK, you have your design exercise prompt. What should you do first? Since this is a high-stakes project, it’s important to get context up-front to save time by executing in the right direction.

What Is the Final Deliverable?

What are they looking for? Is this a mobile app, a sitemap, a research brief, or a desktop app? Are they looking for you to show your skills in interaction design, information architecture, research, visual design? This should be clear from the prompt.

important When you’re working through a design exercise, know when to take shortcuts and know when to go bespoke. Creating every asset from scratch may take a long time and may not be necessary.

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Real-World Take-Home Design Exercise Solution13 minutes, 11 links

Here is a sample design exercise solution that I completed a few years ago. This presentation (as well as the rest of the interview) helped not only secure my offer but led to a higher design level than I anticipated and a higher salary as well. The prompt asked to design a car dashboard for an autonomous vehicle. For this exercise I didn’t have that much time (about five days) so I had to skip my usual approach of asking many questions up-front and started working right away.

As is usual with any design briefs, I began by reframing the problem. Instead of “designing a car dashboard,” I wanted to think about the experience broadly—from the car’s interior to its exterior and how the car can be part of a larger ecosystem. I sketched a few different directions before settling on one, which I fully fleshed out, and lastly, I sneaked in a surprise at the end of my presentation.

Looking at Analogous Domains for Inspiration

To start this exercise, while riding the train to my next interview, I began typing some thoughts on my phone in the notes app on how to approach the task. The train itself was an inspiration—could public transit be the answer? I pursued the mass transit idea further by looking into Emirates airlines and other luxury transit services, including the new luxury Japanese train. The luxurious interiors looked nice, but what about everyday mass commuters? What are their existing activities and habits when taking the train to work?

Figure: Your Own Private Autonomous Vehicle

Your own private autonomous vehicle

I didn’t have time to set up a proper study, so I relied on three 12-minute interviews with friends and asked them about their experience with riding trains, buses, ferries, and so on. From searching online and from the conversations, I identified four major categories of activities on mass transit: productivity, relaxation, social, and health.

Questioning Assumptions

When you’re going deep on the design exercise, it helps to periodically step back and remind yourself about the problem you’re trying to solve. In my case the prompt was asking for an in-car UI design for a self-driving car. I decided to take a slightly different approach because many car manufacturers have been addressing this problem for decades. Redesigning the car display would be optimizing for local maxima prematurely.

Figure: Interior Display vs Exterior

Don't take your eyes off the road

Manufacturers have spent their attention on the interior display taking eyes away from the road.

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Exploring Solutions with Storyboards

With problem discovery done, I did some rough explorations via storyboard sketches showing how a car interior could transform to a suitable activity from an interactive gym inside a car, to a productivity station, to an experience that connects two strangers by showing activities and people they have in common.

Figure: Bringing People Together

Bringing people together

Bringing people together based on shared connections and activities.

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Using Storytelling to Make the Concept Come to Life

To make the concept come to life, I wrote a story about a fictitious solo business traveler, Sarah, who has a few hours to kill in the evening in San Francisco by doing a tour of the city. The solution is an assistant in an autonomous car that understands Sarah and anticipates her needs. It also has a bit of snark to its personality, something Sarah appreciates.

Figure: Meet Sarah

Fictitious personas

Meet Sarah.

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Showing, Not Telling Sarah’s Journey

Here are a couple of highlights from the narrative that I’ve put together. Her journey starts on her phone near the place she’s staying.

Figure: The Journey Begins

The journey starts on the phone…

The journey starts on the phone…

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Putting It Together

The final presentation came down to 40+ slides in four chapters:

  1. Research synthesis. Show already-existing behaviors of people in relation to semi-autonomous and autonomous vehicles.

  2. Contextual scenarios. Show storyboards highlighting divergent exploration, ultimately converging on the final segment of the presentation.

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Outcome

The on-site presentation of this exercise was my third to last interview. I lucked out on the presentation space, as Sarah’s story came to life on a beautiful large display. The box and the rough sketches surprised and delighted the interviewers, as they had never seen anything like it.

This is one way to solve a design exercise but not the only way. I do hope that by showing some of my process behind the work and the deliverables, you can see how I’ve followed (or ignored) the design exercise principles (they’re not set in stone) based on the situation at hand.

The design exercise is an opportunity to leave your personal mark on the work. Take it and have fun with it. Find out what the evaluation criteria will be and use your unique perspective, experience, and knowledge to stand out.

Additional Resources

Coming up with a new design proposal from nothing can be a lot of work. Usually, when you’re joining a company you have frameworks already set up for you, be they design systems, brand assets, or just existing processes that can help you stand up a new concept quickly.

important When you are using outside resources for your design exercise be sure to properly attribute and credit the work.

Many of the assets that I’ve used for design exercises (including this one) came from popular, free-shared libraries. Here are some I recommend for the raw materials for your design exercise.

  • Photography

    • Pexels. Bills itself as a free and inclusive photo and video library.

    • Unsplash. One of my favorites, and the go-to resource for high quality photography.

    • Pixabay. Over a million images and videos shared, free for personal or commercial use.

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Acing the App Critique22 minutes, 10 links

The app critique is one of the easier interviews you’ll encounter when interviewing for a product design role. Unlike the take-home design exercise or the whiteboard interview, you don’t have to create something from scratch.

Unlike a critique of an app that you’re designing, you’re not encumbered by any internal constraints (tech, business, and so on), giving you an immense amount of freedom. The challenge then lies in how to come up with reasonable constraints to help you navigate the critique.

important As you’re facilitating the app critique, ask yourself—can I work with this team if I was hired? Do they seem like people I can bounce ideas off freely?

We’ll cover different techniques that you can mix and match to come up with evaluation criteria for your app.

Interview Format and Criteria

App critiques usually last 30–45 minutes. Typically, you’ll interview with one or two designers. Either you’ll be asked to bring an app for critique (based on interviewer criteria) or the interviewers will pick one for you.

Your interviewers will assess you on:

  • Collaboration. How receptive are you to feedback? How do you react to different opinions? How effectively can you facilitate the critique?

  • Craft. How well can you reverse engineer an app, breaking it down to its first principles?

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Establishing App Critique Objectives

Before diving into the app critique, it’s important to understand how the critique will be carried out. Your interviewers might give you a general prompt like “critique app X” or get specific: “how can app X maximize revenue from its existing customer base?”

In either case, start with high-level objectives:

  • Context. If you’re bringing in an app yourself, let the interviewers know why you’ve selected it. If an app has been picked for you, you can set the context based on what you know about it.

  • Goals. If the prompt is open ended, narrow the scope by establishing goals. What’s the business objective? What is the user trying to achieve? What are we trying to get at in the next 20 minutes?

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Six Frameworks for Critiquing Apps

Now the fun part. Here are six frameworks to help you examine the app:

  1. Jobs to be done. Uncovering the core objective.

  2. Personas. Goals, motivations, scenarios.

  3. User familiarity. New users, intermediate users, and experts.

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Avoiding Common App Critique Mistakes

From my time as an interviewer, I’ve seen a couple of mistakes that designers make when doing critiques for interviews.

  • Stopping at aesthetics. Sometimes it’s tempting to dive right in and point out all the things that look off on the UI. Don’t get stuck on aesthetics. None of that will matter if the app doesn’t help the user achieve its core goal in the first place. Establish your first principles based on the frameworks above and work forward.

  • Stuck on one approach. If you have an app that you’ve already picked yourself, then you’ve already come prepared with how you’re going to critique it. But be ready to adapt your approach and consider different methods when prompted. Doing so also allows you to show off other tools at your disposal, and handling ambiguity is a sign of maturity as a designer.

  • All praise, no substance. I’ve encountered situations where instead of critiquing, the designer lavishes praise on the app. As an interviewer, this tells me that you can’t reflect critically on the work and you assume that whatever’s been launched is best.

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Getting Better at Critique

Like any activity, you’ll get better at critique with practice. To make the most of your practice, I recommend critiquing an app with a group, isolating your weaknesses, and comparing and contrasting similar apps.

Critique in Diverse Groups

Practice critique with a partner or two. Get a group of designers who have different strengths and feel free to include other disciplines, such as engineering. Practicing together with a diverse group will widen your perspective significantly, compared to practicing alone.

Isolate and Focus on an Area of Growth

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Additional Resources

If you’re interested in growing your critique skills, here are some handpicked resources to help improve:

App Critique in Action20 minutes

In this example, we’ll go through Yelp’s iOS app, evaluating the app in a couple of ways. We’ll make our first impressions by examining the home page, and then get a sense of its structure by navigating to different pages. We’ll look into personalization and go through one of the core flows by looking for a nearby restaurant.

We’ll evaluate the app based on its visual and interaction design. We’ll also consider strategy, also known as “product thinking” or “business acumen,” to understand the why behind the UI decisions. Although it’s not our primary concern, we’ll also pay attention to copy and messaging.

First Impressions

You can tell a lot about the app based on its presentation. The visual aspect of design hits us quickly. Based on this first impression, we decide if we want to stick around or go elsewhere. At this stage, we get an idea of the feeling the app is trying to communicate to us—is it serious or playful, trustworthy, or suspicious? These are just some of the questions that go through our heads in a split second.

As designers, our job is to build an experience consistent and in tune with the impression that the business is trying to communicate. As a result, during the critique, we should be on the lookout when a design reinforces or contradicts this consistency.

Figure: Launching Yelp

Launching yelp
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We took some time to familiarize ourselves with Yelp overall and got some interesting data points from the landing page. Now let’s look around. What else can we do? Going through an app’s navigation will help us get a better sense of the content and how it’s structured.

Figure: Delivery, Me, Notifications

Delivery, me, notifications
  1. Delivery. Since most restaurants are either closed or operating at minimum capacity, it’s no surprise that delivery is made prominent as an item in the Tab Bar. One interesting visual element you’ll notice going through the app is that the icons here use a different style than Home and Search. I suspect these styles are probably an evolution of Yelp’s visual language. The carousel on the top implies there are about 20 restaurant categories available, though arguably, it can be visually simplified by removing the carousel dots at the bottom.

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Exploring Personalization

We’ve now done a surface dive on Yelp. Primarily focusing on Search, briefly popping to the App Store and then returning back and exploring the app via the tab bar navigation.

Next up, I’m curious about how Yelp is trying to improve its recommendations via personalization. As previously mentioned, getting personalization right can be useful for a business as relevant content leads to higher engagement and user retention. However it’s how apps implement personalization that makes all the difference.

Figure: Personalization Entry Points

personalization entry points
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Ordering From a Restaurant

Now, let’s take a look at one of the Yelp app’s core flows. Imagine I, the user, am looking for a takeout option in a new part of town.

Figure: Getting Takeout

getting takeout

One way to quickly find a restaurant is to make sure I’m only looking at places that have a takeout option (1). Tapping on Takeout on the Home page brings up the split map/list view (2). This view gives me primarily two paths to take: the map or the list. I don’t want to go far, so while the default radius of the map is useful to see all the options, I need something closer.

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Parting Words of Advice

In this critique, we walked through a common framework to evaluate an application based on its visual design, interaction design, and product strategy. We also tangentially covered motion design and considered copy.

important Remember, depending on the company and the role you’re applying for, you may want to emphasize certain aspects of a critique over others.

This is just one way of running a crit. Based on how you approach this exercise, you may come up with an entirely different flow and evaluation. What’s important is to have a rigorous framework in the first place to evaluate the app against.

Whiteboard Challenge23 minutes, 2 links

story It’s 1 p.m. I’m nervously standing by the whiteboard fidgeting with a marker. I’m only five minutes into the whiteboard interview but it feels like an hour has passed. What was the prompt again? I’m sweating. Is there air conditioning or do they blast heat on purpose? Anyway, I draw a persona and start making flows. Whoops, 40 minutes later I find out it’s the wrong persona, wrong flow, and I’m a hot mess.

Since that one awkward time, I’ve done many whiteboard interviews and had the opportunity to interview new and seasoned designers using the whiteboard challenge. I’ve seen some common mistakes but also best practices emerge from those interviews. While this interview is different from your everyday whiteboard sketch, it doesn’t have to be an enigma. Here’s a systematic approach to take on the challenge, avoid common mistakes, and prepare effectively.

Whiteboard Challenge Format and Criteria

Whiteboard interviews typically range from 30 minutes to one hour. Usually you’ll be interviewed by one or two designers. Similar to the take-home exercise, the whiteboard design challenge is meant to evaluate your skills in a short amount of time with a focus on interaction design and collaboration.

Your interviewers will assess you on:

  • Problem definition. How well can you explore the problem space and identify big problems to go after?

  • Solution finding and idea generation. How quickly can you explore multiple creative options without being married to any one idea and identify the best one to develop further?

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Going on the Journey Together

Since whiteboards are an artificial challenge, it will be up to the interviewer to properly set you up. As the candidate, you’ll be driving the interview. However, since prompts vary and companies have different expectations, clarify expectations with interviewers up-front:

  • What outcomes do they expect to see?

  • How do they want to be engaged?

  • What role will they play in the process: are they designers, product managers, engineering peers, users of the product, stakeholders, researchers, or someone else?

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Approaching the Challenge

Once you have an understanding of the interaction model, the process itself can unfold as predictably as the traditional double diamond design model that’s so often taught in school. Since you’ll be pressed for time, you’ll need to make the call on what steps to accelerate, where to skip, and where to dive into the details.

Figure: The Double Diamond Design Model

The double diamond design model

The double diamond design model. Source: Dan Nessler

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Managing the Whiteboard Space

Just like when you’re presenting your portfolio, you also want to position yourself in a good spot for a whiteboard. This means having enough space for you to write while having your interviewers clearly see what you’re doing. You should also keep track of time, ideally with a timer on your watch.

The surface area of your whiteboard should be proportional to the amount of time you’ll spend on it.

Figure: Managing Space and Time

Match surface area to time
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Finishing on a High Note

Even with great time management, there are usually more problems and more solutions to explore, so it’s very likely that you’ll run out of time. If you’ve been tracking time yourself, pause ten minutes before the end of the interview to take a pulse check—what do the interviewers want to see next? Do they want you to proceed further, or is this a good place to stop?

If you are at a stopping point or if you’ve actually “completed” the whiteboard challenge with time to spare (congrats, a rare feat!) take a moment to summarize and mention how you might have approached the process differently. Balance this self-reflection with time for additional questions that you might want to ask your interviewers.

As an interviewer, I’m also reflecting on our time. Could we work well together? How well did you respond to my feedback? Was your approach different from mine? Can you help me overcome my gaps? Have I learned something new here?

Common Whiteboard Mistakes to Avoid

When interviewing designers, I see many common mistakes made repeatedly. It doesn’t matter if the designer is fresh out of school, mid-level, or senior. Here are a couple of issues that stand out and can be easily fixed.

Overkilling It with Context

As part of the product design interview, it is important that you establish a strong foundation that’s predicated on context and the problem. But you can also go overboard with this and run out of time, so you don’t get to any solutions or you take a very superficial pass at the solution phase.

This is a problem of time management. Context setting and problem definition should take less than half of the interview time. For example, in a one-hour session with 15 minutes for questions, roughly 10 minutes should be used for understanding context, about 10 minutes for problem exploration and definition, and most of your time (about 25+ minutes) on sketching and iterating through solutions.

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Solid versus Amazing Whiteboard Execution

Once you’ve mastered the basics, it’s time to think about what can take your whiteboard execution from good to great.

Solid Execution

A good whiteboard execution hits on many of the things we have already talked about—proper framing, generating solutions, and collaboration.

You’ve taken the time to understand the problem by looking at it through multiple lenses from the business, user, and engineering side. You’ve defined a specific audience or persona to design this solution for. You’ve pushed back on the initial statement by reframing it, perhaps making it broader or more specific or by discovering a new problem altogether. The interviewers agreed this was the way to go.

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Practicing Better with Whiteboard Prompts

The best way to get better at whiteboards is through practice. Baseline yourself initially to gauge your progress. If you haven’t done any whiteboarding, grab a marker and start sketching. Don’t worry about perfection, just get familiar initially.

The prompts vary depending on the company and the space they’re in. Some exercises range from pragmatic to design fiction. Interviewer guides usually include the prompt, variations, and questions interviewers might ask, plus grading criteria. As an interviewee, you’ll be presented with the prompt up-front and then be asked to walk the interviewer through the process. Here are a couple of starter prompts to experiment with:

Growing Gardens, Growing Business

  • Prompt. Growing Gardens targets suburban families who are interested in gardening but have little to no formal knowledge. The business primarily sells plants but is also extending into additional products (pots, fertilizer) and services (landscaping). Create an application to help people learn more about gardening and getting them to

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Baselining Your Whiteboarding Skills

Now that you have some prompts and core criteria, you can start practicing by yourself. Imagine you’re running a think-aloud usability study, but instead of moderating, the participant is you. Record your first-time through and be sure to time yourself. Play back the recording and look for patterns where you pause, don’t speak, or speak too much.

Take a photo of the whiteboard and do a self-evaluation based on the criteria we mentioned in the beginning:

  • What did you wish you could spend more time on?

  • What did you miss?

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Whiteboarding Remotely5 minutes

If you’ve been asked to do a whiteboard challenge in 2020 or 2021—and perhaps even beyond—chances are it’s taking place remotely. Like the on-site version of this challenge, typically you’ll have about 30 minutes to an hour to complete this interview. Instead of a traditional whiteboard in a conference room you’ll be given a few options as to which tool you want to use.

In general, these options fall into two categories—analog or digital. Analog tools such as a notepad or an actual whiteboard may feel familiar and fast. Digital tools that allow you to share the document live in the cloud may make it easier to collaborate.

ToolProsCons
WhiteboardJust like the real thing at a regular interview setting.If you don’t have one already, buying a large whiteboard can get pricey. May not be readable through a laptop camera.
Paper notepadCan be a great way to sketch out ideas, cheaper than buying your own whiteboard.As with the whiteboard, camera quality will play a role in how your sketch looks.
Tablet (e.g. iPad)Using a tool such as Procreate allows you to quickly sketch ideas.Requires you to maneuver the device so that it’s visible to the interviewer.Taking notes may take longer compared to sketching.
Design tool (e.g. Figma or Sketch)No new tools to learn, easy to move around, sharing the file on the cloud makes it easier to collaborate.Be careful not to waste time polishing pixels.
Whiteboarding tool (e.g. Miro, Mural)Easy to get started with sketches quickly, and cloud share aids collaboration.Getting things precisely mocked up may take a long time and may not feel as fluid as a dedicated design tool.

If you’re not sure which tool is best, pick the one you’re most comfortable with. Interviews can be stressful enough and you won’t be doing yourself any favors if you try to learn a new tool at the last minute.

Set Your Environment up for Success

If you’re choosing to go the analog route, be sure to test your camera set-up and quality ahead of time. It may be worth it to invest in a standalone camera, as opposed to the one that comes with your laptop, because you can easily reposition the camera to point to your notepad or whiteboard while still seeing the interviewer on the screen. Alternatively, you can dial into the meeting with your computer and your phone—using your phone as a standalone camera to point to the sketch.

Modern design tools allow you to share your file on the cloud, which may make collaboration easier while conserving video bandwidth. As an example, if you’re whiteboarding on Figma, you don’t have to share your screen, thus conserving bandwidth. If connectivity becomes an issue you can turn video off and go with audio only.

Regardless of which tool you pick, you may still run into interruptions or connectivity issues. Make sure you account for those and think how you’ll respond when they happen. Having a plan for these now will make it easier for you to navigate these speed bumps as they occur.

Figure: Managing a Remote Whiteboard

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Keep Collaboration in Mind

One of the challenges of the whiteboard is that you may not be able to see the interviewer’s body language. This becomes especially challenging if you’re sharing your screen and the interviewer becomes a small rectangle off to the side. In these cases, it helps to pause and check in with your interviewer from time to time. Since you’ll be primarily driving the interview, you can stop periodically to ask, “Are you with me?” or “Do you have any questions so far?”

important As you know, the key criteria for a whiteboard challenge is collaboration. The remote flavor of this challenge offers a glimpse into how you may work with this designer in the future. Are they collaborative and encouraging? Make sure you write down your thoughts after the exercise.

Practicing Remotely

When you’re solving design problems, one easy way to get a hang of things is to start with the simplest method possible. This could just be a notepad where you could sketch and document your ideas and process. As you get further along in your practice, I recommend switching to the final tool of your choice. This could still be a notepad, or if you do want to go the digital route (which I highly recommend), practice whiteboarding there. Consider your practice complete when the tools have become second nature, you’ve developed a robust system for solving design challenges, and can quickly frame up the problem and the solution.

Part V: After the Interviews

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Interviewing is a process of continuous learning and self-reflection. Sometimes we find ourselves in the middle of an interview with one company just after having recently wrapped up a final interview with another company. Periodically stepping back and noting down your performance will help you continue to improve your interview skills and thus increase your chances of getting that dream role.

When you’re interviewing, inevitably your application will get rejected. Rejection stings, but by conducting your own retrospective and by asking for feedback, you can use it to your advantage. Instead of repeating the same mistake again, you’ll know what not to do next time. Don’t skip the step of asking for feedback—it may make a difference between getting a job or not in your next interview.

Once you do get the role, don’t stop. Accepting an offer too quickly can be a risk if the company has certain red flags (for example, poor culture or lack of runway). Be sure to schedule interviews of your own and do the due diligence to make a more informed decision while negotiating the offer.

Post-Interview Retro5 minutes

You’ve wrapped up your final design interview! At this stage, you might have an interview lined up right after or you may be early in the interview process with other places. Regardless, it helps to step back and reflect on the day. Also, don’t forget to close strong by thanking your interviewers for their time. Some say that thank-yous are passé. I disagree. Sending a specific and thoughtful email is an extra touch that reinforces your interest in the role.

Figure: Post-Interview Retro

post-interview retro

To begin, grab a piece of paper and fold it twice to make three columns: celebrate, improve, learn.

Celebrate: What Went Well?

When we’re in the middle of interviews, things happen fast. Sometimes there’s little room for thinking, and if you’re an introvert you may feel overwhelmed by the constant barrage of questions. So it helps to step back after the interview and celebrate the things that went particularly well:

  • How did I set myself up for success during the interview?

  • What question(s) did I pass with flying colors? What made it good?

  • How did I closely connect with one of the interviewers?

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Improve: What Could Be Better?

As you step back, try to view through the eyes of an outside observer, as if you’re watching yourself and the interviewer from the sidelines.

  • How did you come across?

  • What did you miss?

  • What could you have done better?

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Learn: What Did You Find Out?

I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.Maya Angelou

Another thing to note is what you learned and how you felt during the interview.

story “What’s your favorite brand?” asked the hiring manager during an on-site interview. I paused to think, as brand wasn’t my forte, but gave an explanation for why I thought Airbnb was doing meaningful work in experiences. “I hate Airbnb. What’s your next one?” she shot back. Later she proceeded to tear apart my portfolio. This interview was enough for me to learn everything I needed to learn about this company’s culture.

The interview is a two-way street. You and the interviewer get to know each other and build a shared understanding.

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Learning From Rejection14 minutes

You’ve wrapped up your product design interviews and are now waiting to hear back. But a few days later you get that dreaded reply thanking you for your application, but it’s “not a good fit at this time.” What happened?

Figure: A Generic, Cryptic Email

Generic, cryptic email

You might get this generic, cryptic email. 🤔

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First Step—Ask for Feedback

So let’s say you got an email similar to the one above. Now’s a good time to follow up with the hiring manager or recruiter or both and ask for feedback (thus demonstrating self-awareness and a growth mindset in the process).

Here’s a general template to follow:

  1. Thank them for giving their time.

  2. Mention how you’re interested in the role and would like to be kept on the radar even if now’s not the right time.

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Framework for Working Through Feedback

Over time you’ll accumulate different and potentially conflicting feedback. This is why it always helps to have a career roadmap for your next step in the journey. Some feedback will be relevant—some won’t be. A roadmap helps you prioritize.

Figure: Breaking Feedback Down
Break feedback down into quadrants

Break the feedback down into quadrants.

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Reasons for Rejection

Although a company really wants to fill that vacant design role, the cost of a bad hire is high. Companies hire conservatively. So even though they need help (and they stretch existing employees to fill the gap), many choose to wait longer to find a perfect match. That’s why it’s important to leave a strong impression and convince your interviewers that you’re the right designer for the job.

To be clear, “a perfect match” doesn’t actually exist. Don’t eliminate yourself by not applying to roles where you meet 70% of the requirements. If you have the skills, you can pick up the other 30%. What’s important is to communicate to your interviewers that in addition to your know-how, you have the ability to adapt and learn fast.

You can ensure you and your interviewers are on the same page by asking them point blank:

“Is there anything that I said or didn’t say that would make me not an ideal fit for this role?”

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Some Rejection Is Healthy

Sometimes a lack of rejections can be a red flag too. You might actually be setting your goals or aspirations too low if you’re not getting a good dose of rejections during your interviews. Think of rejection as inoculation against further rejections, helping you get better over time.

What to Do When You Get the Offer14 minutes

You’ve landed that dream design job after all those interviews. This may even be your second or third offer. In either case, good on you for coming this far. The hard work paid off and the tables have turned. Before you accept the offer, do some homework to set yourself up for a strong head start in your next job. Now you’ll get to play the role of an interviewer to see if hiring this particular job will be best for your career.

When companies hire executives, they usually go through an intensive interview process of getting the dirt behind the candidates. You should follow a similar process. With an offer in hand, take the time to get your questions answered about the company, opportunity, and team so that you can make a well-informed decision.

important Skip the email Q&A—set up a coffee chat (or a conference call) instead. Body language and voice can sometimes be more telling than the answers themselves.

Interviewing Your Direct Team

To start, you should talk with people you’ll be working with daily—a fellow designer, engineer, or a product manager. If there’s only one person that you can get to interview from your direct team, I would recommend talking with the product manager. So much of your day-to-day will be spent directly working with them. Understanding how they think about customers, design, and user research will help you get a much better clue of design maturity at the company.

Interviewing Your Design Manager

If you haven’t had a chance to talk with your design manager during the interview process, definitely make the time to do so now.

You should feel confident that this manager is someone who’s going to help you grow. If something feels off, now’s a good time to clarify. A good manager is like a coach—they’re there to set you and the team up to play your best. They’ll navigate tough decisions with poise. No manager is perfect, but finding someone you can get along with well will make a big difference over time.

important If you’re joining a small company such as a startup, consider requesting a skip level meeting by asking to talk with your manager’s manager or the CEO of the company. In smaller settings the leadership team has an outsize impact and can make or break your experience. How they respond to your questions will help you better gauge the company’s design maturity.

Interviewing People Who Left

Now of course, current company employees will be biased in favor of the company. It’s rare that someone will tell you that the org isn’t in good shape or that the work environment is stressful. So it helps to get a second opinion. Talk to a former designer if there was one. Sometimes interviewing the people who just left will give you an unbiased view of the workplace you’re about to join.

story When I was getting background info on one of my managers, I looked at his connections on LinkedIn. One of those connections—let’s call him David—worked with my manager a few jobs ago. Coincidentally, David also worked closely with a CEO of another company that I interviewed with. Small world!

Questions You Should Consider Asking

As you’re reaching out to folks and setting up coffee chats, it helps to have a strong question list ready that gets to the heart of the matter. Just like interviewing users, you don’t want to ask leading questions but instead get at the truth by asking about existing behaviors.

I recommend you get a clear signal on the work, work-life balance, the design team, the company’s design maturity, and—if it’s a startup—how much runway they have left.

The Work

Here are some good questions to ask your design manager.

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Making the Decision

When you get an offer, take the time to zoom out before you zoom in. If you were to take this role, how will it help you achieve your current and future goals? Ultimately, we’re all captains of our own ships. A good job is one that pays well, grows your skills, and advances your career. Of course, choosing a job isn’t all about career aspirations either. Work-life balance is also key. In the end, you should weigh factors based on how important they are to you.

Remember the mapping your futures exercise exercise that we did earlier on? Now’s a good time to reflect, since you’ve been through the process and a few weeks have passed by since then. Are your fundamental goals still the same? Have they changed with new information?

important There will never be a sure thing or an ideal workplace. Companies reorg, teams change, projects shift. The best you can do is to look at core factors (such as culture) and the key people who influence the process so that even in the times of reorg, you’ll still end up in a good place because the culture of the company is one that resonates with your values.

Choosing Among Multiple Offers

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Breaking Down Your Design Job Offer12 minutes, 10 links

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When we think of negotiation, we think of it as the final step between you and the job. The reality is that we’re always negotiating. Sometimes you’re not even in the room. Your work, your portfolio, is negotiating on your behalf, especially in the beginning—so be sure to make it strong. Show that you’ve achieved outstanding results in the companies you were with and this will lead to proper leveling and help the employer set the right expectations for a salary range.

Compensation FAQ

What Do I Say when I Get a Call Congratulating Me?

Stay positive and convey your excitement for the role. The next step is to get the offer in writing so you can pore over it in detail. The employer wouldn’t expect you to commit on the spot, and it’s reasonable to ask for time to think things over.

I’m Not Sure if I Want to Work Here…

If you’re still on the fence about taking the job, get answers to your questions first by interviewing your future teammates. As part of your interviewing, you can also ask about job expectations and career ladders. What does success look like? Who is a good example of a strong designer there? Return here when you’re mostly certain.

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The Compensation Package Breakdown

When you receive your compensation package, you’ll be leveled at a band, which comes with a range; for example, associate product designer makes $100K–110K base salary compared to a product designer who might make $110K–125K. In general, the company that you’re considering should have an objective standard for determining salary ranges, and you can always ask how they’ve arrived at their decision.

Years of design work serves as a rule of thumb when it comes to compensation, but years of experience doesn’t always equate to expertise. Ability to ship products that led to phenomenal outcomes does. Prove that you can perform at a certain band and have deep expertise that the company doesn’t have—you’ll get compensated appropriately.

Base Salary

Base salary is usually shown as a pre-tax annual number. If you’re moving to a new area, be sure to factor in your cost of living plus various taxes. According to Hired’s State of Salaries 2019 report, the average tech salary is highest in the SF bay area at $145K. However, Austin, TX, wins out since it has a better cost of living and so the same salary brings more purchasing power. In addition to your base salary, it’s helpful to understand how often the company does performance reviews, as these are additional opportunities to recalibrate your salary. Typically they happen either once or twice a year.

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Negotiating Compensation14 minutes, 9 links

Start with the end in mind. Before entering a negotiation, think through the factors that are important to you now. You don’t have to have a five-year vision—not many do. But having a solid plan for your next year, what you want to learn, and the type of work you want to be doing will help you meaningfully make trade-offs.

Not a Zero-Sum Pie

When we think of negotiation, it’s not unusual to think of it as a zero-sum game. One player takes most and another is left with less. But that’s a losing proposition. You should reframe a negotiation as a conversation to come up with a win-win situation for both parties. This will lead not only to a good short-term outcome for you but also to long-term goodwill down the road when your next assessment comes.

important A good negotiation should feel like a productive collaboration between two teammates.

Stay enthusiastic about the role throughout the negotiation process as you’re building rapport with the recruiter. Thank them for the concessions as you’re approaching the offer together. Mention that you appreciate their willingness to listen and be flexible. Graciousness goes a long way—don’t miss an opportunity to make the other party feel fabulous. You’ve already built trust throughout the interview process; use the negotiation as a way to further reinforce your goodwill.

In turn, be willing to listen. Empathy is a designer’s master skill. If you can truly understand their issues, and the true issues behind those, you can come up with a creative way to solve the compensation problem while putting them at ease and moving closer toward your end goal.

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Understanding Your Level

Your total comp is determined by a company’s leveling framework. The more senior you are, the more experience you have, the more money you’ll get. At higher senior levels your compensation will be predominantly based on your performance and will be closer tied to your equity.

In certain organizations, being brought on at a certain level sometimes acts as an anchor. That is if you’re starting out at mid-level you may need to prove yourself for a long amount of time before getting promoted to a senior role. That said there is also a risk of coming in at a level that’s too high or setting yourself for a bar that you cannot meet.

After you join the company, the leveling document will be used as objective criteria to evaluate your performance and determine whether you’re not meeting, meeting, or exceeding the criteria set forth. While the common hustle advice is to “fake it ’til you make it”, sometimes there is no making it. Instead you’d be better off in a place that strikes the right balance of playing to your strengths while giving you an opportunity to grow without so much stress that you’re not able to do your job.

Every company will have their own leveling guide which in great detail shows what one needs to do in order to perform at a certain level.

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Demonstrate Your Strengths

Negotiation starts when you first start applying, so look for opportunities to reinforce the unique skills and knowledge that you bring to solve a specific pain (or multiple pains) for the company.

story When I was applying through job boards (which is one of the worst ways to apply, by the way), I was able to score an interview at a well-known tech company due to advanced prototyping that I’d done previously. It was demonstrating the work in-person and letting the interviewers use my prototypes on their own that helped land an amazing offer.

Think of negotiation broadly. It’s not something that happens just at the end—a strong start can make a huge difference toward your final comp and leveling. But let’s say you already are at the end—it doesn’t hurt to reiterate the unique value that you bring.

important If you want to get compensated highly, you need to understand a company’s key pain points. Show that your unique strengths can resolve these issues.

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Use Multiple Offers to Your Advantage

If you’re in a lucky position to have multiple offers, be sure to compare and contrast. Talk with the recruiter about matching your highest offer’s salary. At this point you have some advantage here, as a company would hate to lose a qualified candidate to a competitor. Beyond salary, you can negotiate equity or maybe sweeten the deal with a one-time signing bonus.

Understand that interviewing candidates is a long process. They’ve just gone through rounds of writing the job description, reviewing candidates, going through phone screens, and getting designers to spend their time interviewing you and other candidates. Finally, they narrowed it to one offer—yours. This whole process usually takes money and time, and time is the most painful factor. They’d rather not go through a month and a half of work again.

important If you don’t have multiple offers outstanding—don’t let this deter you from negotiating. Even starting the compensation negotiation process already increases your chances of getting a favorable outcome.

Accelerate the Interviewing Process

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Conditionally Agree

The first step in negotiation is understanding the needs of your client. Since you’ll be working closely with a recruiter and they have a quota to fill, you can assure them that you’re serious about the offer by saying you’ll accept it right away if they can get you X. X can be anything that’s important to you and is not just restricted to salary.

Saying no can feel like placing an ultimatum. As we’ve talked about earlier, a negotiation is like a conversation (but with high stakes). If you’re getting close to what you hope you’re getting, you can say no in a non-confrontational way—“Thank you for showing flexibility on salary, this seems appropriate. Could we talk about other things that factor into compensation?”

Again, this will reinforce the image of your flexibility and allows you and the other party to examine compensation in a safe way.

When Your Dream Job Won’t Budge on Comp

You’ve played your cards right, done your homework, and negotiated with multiple offers, but still the company won’t budge. Hey, at least you’ve tried and you’re still ahead of most folks who don’t even ask. You still have a couple of options.

Shift Amount of Salary versus Equity

If you’re negotiating with a startup, the company simply may not have the money to give you a higher salary, as everyone is already taking a pay cut. Potentially, this is an opportunity either to ask for an increase in equity if you think your compensation package isn’t in line or to better understand how subsequent rounds of raising money will affect your compensation.

Finally, as a method of last resort you can also scale down salary in favor of equity or go the reverse route and ask for more cash with a lower equity stake. In doing so, you need to understand how this will impact your future performance reviews. Are you only going to be compensated with raises in extra cash, or can extra equity come into play as well?

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Final Words on Negotiation

When you’re joining a company, you’re not just getting paid—you’re also buying into their culture. Ideally, you’ll end up in a place that has good salary, good work, and good people. The day-to-day will be far more important to your long-term sense of achievement and success. If you’re always stressed about the commute, or if it feels like the co-workers don’t have your back, it will eventually translate to not just worse performance—it will ultimately lead to burnout, forcing you to look for another job.

important Negotiation is a critical skill for designers. It’s not just something you magically get better at during a few critical moments where it counts. We don’t get to practice it as often as we need. Aside from practicing, it helps to learn what to practice. If I had to recommend one book on negotiation, it would be Never Split the Difference. Written by an FBI hostage negotiator, the tactics are made applicable to many areas of life, “in the boardroom or at home.”

Additional Resources

To learn more about design levels and how various companies structure them:

  • Intercom’s individual contributor design levels and design manager levels, in addition to being open available and detailed, have specific objectives and growth tasks tied to each level.

  • Basecamp’s Titles for Designers. Although Basecamp is a small company by startup standards, their design framework is rigorous. Aside from describing what are the different expectations of designers, it also publicly lists the names of designers at those levels.

  • DoorDash’s Head of Design, Helena Seo, shares her thinking and approach toward creating a leveling system at the company.

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Leaving Your Job on a High Note7 minutes, 1 link

You’ve accepted an offer, negotiated it, and now all that’s left is to tell your current company that you’re moving on. First off—congrats! Success in design is often nonlinear. It’s not about going to an expensive university to end up working for a prestigious company. Great designers know that. They’ve oftentimes experienced different cultures, worked with different people, and have seen industries shift. They understand that you can’t learn everything in one place.

Here is how you can quit well, set your current team up for success, and prepare for your next opportunity.

Finishing Strong

The first person to tell about your leave is your manager. It’s likely that they’ll try to persuade you to stay and offer some sort of incentive, such as a higher salary. If your current job isn’t meeting your needs that you hired it for, stick to your principles. People usually don’t quit over salary. If you got to this point, it’s likely that there’s a list of things that aren’t going well at your current job. It’s bittersweet to say goodbye and venture into uncharted territory, but if you’ve done your homework, the move will be worth it.

important Ask yourself: If somebody were to pick up your job today, how can you set them up for success?

Depending on where you’re working, the law is usually flexible. In the United States, many states have “at will” employment, which means you can quit or get laid off at any time. You don’t even have to have the conversation with your boss; just write your letter of resignation and be done with it.

It would be, however, a disservice to your team to leave so abruptly. This is especially true if you’re the only designer at the company. If somebody were to pick up your job today, how can you set them up for success? Can you pay your expertise forward? One of the things that I appreciate in my current role is the strong design system that a prior team has put together. Even though I didn’t have the opportunity to overlap with them, their work stood the test of time on its own.

Recommend a Good Match for Your Current Role

We leave jobs because they don’t serve our needs well, but this doesn’t mean that this job can’t be a perfect fit for someone else. So if you know someone who’s interested, let your team know—doing so will help them get back their footing quickly.

story When I decided to leave one of my jobs for grad school, I started actively looking for a replacement. I reached out on local UX job boards and pitched the job at a number of design events as well. Eventually I met a designer who was not only excited about the role but also had relevant industry experience. I introduced her to the company, helping her get a head start on the interview process.

Saying Goodbye

If you already have regular one-on-ones with co-workers, now’s a good time to sync up for the last time. Take advantage of these to express your gratitude and thank your co-workers. This is your last opportunity to give feedback, highlight their successes, and share the good times you’ve had together.

One of the things that I appreciate about our design industry is its tight-knit sense of community. Investing in and developing professional relationships, regardless of the company, is key. These people may follow you later. Or you may follow them to another role in a new company. You never know. Companies come and go, but relationships last.

On that last point, make sure to send out an email thanking folks, and leave contact info (usually a personal email) to stay in touch.

When You’ve Had Enough

On the other hand, you may totally hate your job. This gig has been driving you nuts. You feel underappreciated and overworked. No one really seems to care. If that’s the case, resist the urge to (metaphorically) flip a table.

Yes, this situation isn’t good. A two-week notice isn’t required but is typical. Do the best you can and wrap things up. As Tina Seelig recounts in her book, What I Wish I Knew When I Was 20, an employee who was quitting refused to help during a critical time and as a result, “the damage she did to her reputation during the last weeks of her employment dwarfed all the positive things she had done in prior years.” Take the time to wrap things up as best you can and move on.

Take the Time to Reflect

While the recruiter or even the hiring manager at the next role might pressure you to start as soon as possible, don’t give in. The time that you spend between your (now) past job and your future job is just as important. Use it wisely to rest and reflect on your experience.

If your previous job has caused you to burn out (or if you’ve burnt out multiple times already), then rest should be top priority. Don’t try to do much work during this period. Disconnect fully. Catch up on what you’ve been neglecting.

Once you’re refreshed, take the time to reflect. This is a good time to revisit your original job framework:

  • Where are you in your career now?

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Starting Your Job Strong16 minutes, 2 links

In tech jobs, two-year stints are becoming the norm. If you started working at 21 and retired at 65, that’s potentially 22 jobs and 22 different onboardings. This number may be higher if you’ve worked for startups, since some companies don’t even make it past the first year. Regardless of the company, ramping up to a new role poses unique challenges. Although companies usually have an onboarding process in place, many of them are short and aren’t role-specific. Don’t leave this crucial part of the process to chance. By structuring your own onboarding, you’ll be able to build strong relationships, avoid pitfalls, and create momentum toward great work and your next promotion.

important Every onboarding will be different. Depending on the size of the company some phases may take about a month each. Some phases may be a quick affair while others may drag a little as you get into the details. In a small startup your onboarding may be compressed to a week or even a few hours. So take these as a starting point and be sure to adjust them to your context.

Before You Start

It may come as a surprise, but your onboarding starts with your first interview. Treat it as an opportunity to ask questions as if it’s your first day working at the company. Of course, you won’t learn everything here, so be sure to follow up with interviews of your own after you get the offer. When you accept the role, ask your manager if there’s anything you should study ahead of time. Even if there isn’t, this shows initiative on your part to get going fast. You want to be sure to do two things before you dive in:

  • Close the previous chapter. When you’re transitioning to a new role, take the time to rest and reflect. Even a small break will give you enough distance to close out the previous work chapter and savor the future possibilities of your new role. Don’t make the mistake of jumping right in without proper recovery—you won’t be able to start off as strong, and you may even burn out in the long run.

  • Create your learning plan. After a period of rest, plan what you need to learn and accomplish by the end of day one, week one, month one and so on. Adjust your plan as you gain new knowledge, of course, but planning now will help you keep your career priorities in mind, especially when you hit the inevitable snags. Even if there are none, this shows initiative on your part to hit the ground running.

Phase 1: Be a Sponge

During this phase, you’ll be in full-on learning mode. It might be tempting to start fixing things right away, but knowing the context, the system, and its people will help you push for change effectively later.

Key objectives for this phase include:

  1. Gather context.

  2. Set expectations with your design manager.

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Phase 2: From Learning to Execution

This phase, you’ll start to shift toward execution.

Key objectives for this phase:

  • Learn about adjacent teams.

  • Continue building relationships with your immediate team.

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Phase 3: Accelerate Impact

By the end of this phase, you’ll be a trustworthy, well-versed insider who’s up to speed on process, team, and the inner workings of the organization. Your challenge will be to keep this momentum going.

Key objectives for this phase:

  • Become efficient.

  • Amplify impact.

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Land Well and Own Your Career8 minutes, 2 links

By now, you should know the nuts and bolts of how to land your dream role. From taking stock of your various skills, building your identity, structuring your portfolio, and navigating the various interview types, to reflecting on the feedback and wrapping things up with negotiation and a strong start.

As we know, design is never a linear process from A to B, and often there’s a big, messy middle. Knowing how to get to your dream role comes with an understanding of what skills you bring to the table and how to properly communicate them in various stages of the process. Reflecting on your experience throughout these stages is key, as usually new information comes in to help us steer our job search in a favorable direction. While each journey is unique, having a destination in mind makes navigation easier.

Is Remote Work Here to Stay?

Over the course of writing this book, in the midst of the COVID-19 pandemic, the way we get work done (and how we interview) has shifted dramatically. The journey has been redefined. Gone are the days of in-person interviews—now you can talk to many companies all from the comfort of your home.

Of course this brings new challenges. It’s hard to get a feel for a place when all you see is a bunch of faces in rectangles on Zoom. Networking is no longer an in-person affair but has been pushed online as well. Maybe location isn’t as critical as we once thought. If we can get our job done remotely, especially in the midst of a pandemic, then this can usher in a whole new world of flexible work arrangements, opening up opportunities outside of the traditional tech hubs of the world.

When Should You Start Looking?

A common question that I sometimes get from folks who are already working is, “What’s a good number of years to stay at a job before you start looking?” Ideally, you’re in a place long enough to make an impact, and you outgrow the position or the company. There’s nothing left to learn, there’s not a clear or appealing path to growth, and you may see a more fruitful opportunity elsewhere. Sometimes this means being at a job for a few months, other times it means working at the same place for a decade.

Of course there are exceptions to this. The company may be doing poorly, is downsizing, or it has a toxic environment that wasn’t apparent during the interviews. This could all happen, and there’s no imperative to stay at a company that doesn’t invest in you. Today’s world offers designers a lot of challenges to address. The trick is to find the right alignment given your strengths and needs.

In her excellent book, Ask Me This Instead, Kendra Haberkorn recommends candidates ask themselves why they would want to run away from a particular job. Sometimes these reasons can be obvious. Other times you might need to do a little soul searching to think about what you value in work and see if these values have changed since you last searched for or accepted a job.

I encourage you to write your reasons out. Similar to the §interview retrospective exercise and your §reflection at the end of your onboarding—think about the things that are working, what could be improved, and what you’ve learned. In doing so, you may not actually need to look for work, potentially many of these can be fixed on the job through some conversations with your manager. Kendra also suggests asking yourself what job you would run towards. After all, you don’t want to leave a place out of anger just to find yourself in a new role that’s just as bad or worse. Preparation is key—and figuring out what you really want and really value is part of that.

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Own Your Future

If your job search is over and you’ve signed an offer, you might wonder, “What’s next?” First of all, congrats, landing a role can be a challenging process and you’ve proven yourself to be a top candidate. And don’t let that imposter syndrome get in the way—the decision to hire you has been made. Now it’s important to concentrate on the work at hand, to accelerate and grow.

When some time has passed, I always encourage folks to revisit their ideal role template. Take a pulse check about every six months or so. Are the things that brought you to this job still there, or have things changed? Depending on the company and market, the rate of change may be drastic. Or maybe there were no changes to the company at all but perhaps your own needs have changed. Revisiting your original dream role North Star will help you continue steering your career in the right place with new information.

Landing a dream job with a great salary is just the beginning. It’s what you do afterwards that will set you up for success, whether it’s in your current job or the next one. Take another look at your skills and traits. If you’re interested in getting promoted, make sure you bring that up with your manager so that you can work on a development plan together.

Design is a changing discipline. While fundamental principles of human behavior remain the same, technology is changing rapidly. Stay up to date, continue learning. These core skills will help you perform well on the job and will also make you a strong candidate so that you can write your own ticket and define your future.

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Appendix: Resources13 minutes, 80 links

All the resources that were mentioned in the book in one place.

Acknowledgements

A frequent question I get from folks is, how long did it take to write this book? Although the content took only two years to put together, the reality is that I’ve been thinking about the topic of design, careers, and development for over a decade. And although my name is on the cover, rest assured many people supported me on this journey; there wouldn’t be a book without them.

First and foremost, I’m grateful for the support of my family. I spent a fair amount of time writing parts of the book while on vacation, which sometimes meant locking myself away in my room for hours on end. Thank you for being patient with me during this time.

A big shout out goes to the fantastic team at Holloway. Courtney Nash helped start the conversation encouraging me to write. Her support and guidance helped me create a strong narrative from beginning to end. Taking the book to the finish line was no small feat either, and I have to thank Joshua Levy and Rachel Jepsen for helping me get there.

Big thank you to Fabricio Teixeira and Caio Braga at UX Collective for supporting my writing over the past few years. Shout out to Fabricio for feedback and encouraging words which buoyed me to continue writing during a challenging time in my career. And of course, I’m indebted to everyone who has read my articles, shared the work, downloaded the templates, and provided feedback.

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