Ask Me This Instead

Flip the Interview to Land Your Dream Job

Kendra Haberkorn

I’m going to tell you a secret. The most important questions asked in an interview process are those the candidate asks the interviewer, not the other way around.
110 pages and 30 links — last update 20 days ago


Rachel JepsenEditor

Introduction10 minutes

I have 15 years of experience interviewing thousands of people, expertise in designing interview processes, and I coach individuals as they search and interview for new jobs. I’ve read books, dissected online reviews and articles, consulted hiring managers and leaders in order to build a series of conversations that let teams hone in, assess, and hire the people they need and believe can do the job. I know a lot about interviewing.

And I’m going to tell you a secret. The most important questions asked in an interview process are those the candidate asks the interviewer—not the other way around.

Of course, this isn’t the way we’ve been trained to think about interviewing. When you sit across the table from a hiring manager or prospective team member, you’re focused on sharing your experience and skills in a way that convinces the interviewer that you’re the right person for the job. While hiring teams are making a single decision—whether to move you to the next step—you are making many decisions throughout the process. Decisions that will change your career, and possibly your life. I wrote this book because I believe candidates can get a lot out of the interview process. Whether or not you receive an offer or decide this is the job for you, preparing for and ultimately sitting through the interview is an opportunity to think about yourself, what you can offer, and what you really want.

Throughout my career, I’ve done the job I was hired to do by creating systems, hiring criteria, question guides, and scorecards. Those tools, as well as the training and techniques behind them, were valuable. At the same time, I always felt like the hiring process was missing the mark in a major way. The interviewers, questions, and type of assessments are designed to help the team get a 360° view into a candidate’s capabilities and potential to fulfill the responsibilities of the role. With the emphasis on designing to achieve the company’s objectives, I rarely had the time, the directive, or the incentive to design for the candidate (aka, you, the person reading this book and preparing for upcoming interviews). I didn’t have the chance to ask myself, what would make this process better for you? After all, what was best for you had benefits for the team and company as well. When both the individual and company get what they are looking for out of the process, there is an increased likelihood of success and satisfaction as well as the opportunity to proactively address any gaps before someone starts, setting the stage for a smooth onboarding process.

When I’m conducting the interview, I save time for a candidate to ask me questions. Several years ago, I realized that this portion of the interview felt like déjà vu; a significant portion of candidates, regardless of their discipline, seniority, background, or other factors, were asking me the same questions.

In return, I recited the same answers. My responses were true—I always wanted to give an authentic answer but the words were “canned.” I didn’t have to reflect on my experience or think critically about some aspect of the company to provide a compelling answer that was relevant to that candidate. I would customize or connect dots in some way, but the building blocks sections of my responses rolled off my tongue with ease.

I started to keep a document of the most common questions, particularly the ones I was most tired of answering. Every now and then, I’d open it and add to the list. Over the course of a couple of years, the list grew. Sometimes, I found myself wanting to intervene during those last few minutes of interviews. I would feel the urge to stop the conversation and share a few ideas about what I thought the candidate should ask to get the most out of our time together. After asking them questions for 30 minutes to an hour, I knew about their experience, motivations, strengths, and development opportunities, and had insight into the things that they might want to know, but hadn’t thought to ask.

Most of the questions candidates did ask were so broad and generic that I responded in kind—saying what amounted to a lot of nothing. It bothered me. I was invested in the process. I wanted the team and their new hire to be successful. Yet, the interview process for many candidates barely broke the surface of the discovery and exploration that would have enabled the candidate to really dissect, digest, and determine if this was really the right opportunity for them. For candidates to have those revelations was in our best interest—the more we all knew about what the real working relationship and environment would amount to, the better off we’d all be. As a talent leader, I knew that the gaps in the interview process on either side were often the roots of the problems that would follow later.

As a team member, I also knew the dirt—the pain points and problems they were likely to encounter. I understood the organizational and interpersonal challenges that would emerge when the politeness of the interview and onboarding process faded away. I remembered the responsibilities that didn’t make it into the job description. With my broad view into different departments, I had insight into the hidden aspects of the company and team. I wanted them to ask me about those things! To challenge me in order to uncover the real details of working at the company or for a particular manager. Then, if they had the chance to step into the role they wanted, they would do so with eyes wide open.

When those issues came up, or when someone left because the job or team didn’t meet their expectations, I was often left thinking, “I wished you’d asked me this instead. I would have told you what you wanted to know.”

I want you to get as much value out of the limited time available within the hiring process—to be able to explore the priorities and topics that will make a difference in your decision. And that’s what this book will empower you to do. There are five sections to this book that will help you proactively plan for and adeptly navigate the interview process as you seek out and succeed in getting your next role.

  • Target Companies and Evaluate Roles. In this section, I’ll help you evaluate open roles and companies, interpret incoming information and available resources and start to prioritize and refine what really matters to you, right now. With this information, you can target your search, effectively prepare for interviews, and stand out relative to other candidates.

  • Write a Resume That Tells Your Career Story. In this section, you’ll create a stand-out resume that reflects your experience, your priorities, and where you want to go. Activities will help you identify the characters in your career story, map out pivotal moments, connect your story to a company’s needs, write a cover letter, and much more.

  • People and Power in the Interview Process. In this section, I’ll break down the obvious participants and those who can play critical, if less visible, roles in determining whether or not you get the job. I’ll provide you with insights to navigate these conversations and develop strong relationships. You’ll learn how to target your questions to each specific person to get the information you need, and make the right impression.

  • Ask Me This Instead. In this section, you’ll find the Ask Me This Instead question database, with over 100 questions that can be filtered by targeted interviewer and topic. I’ll help you reframe typical questions that candidates ask interviewers to go deeper so that you get more honest, authentic, and unplanned answers. The more you can get beyond the canned, sales-pitch responses, the more you’ll gain. Great questions will give you confidence. You’ll learn why you shouldn’t leave the “asking” up to the interviewers and how you can drive the process. In this section, you’ll also complete an activity to help you design your interview game plan and keep track of what you learn.

  • Warning Signs in Interviews. In this section, I’ll highlight behind-the-scenes scenarios that could impact your hiring process and eventual experience on the job so that you can recognize and proactively address potential issues.

  • Developmental Career Strategy. In this section, I’ll make the case that the cycle of reflection and interviewing will help ensure you get the job you want now and the career you want in the long-term. I’ll direct you to change the way you approach the job search from a time-bound and outcome-focused task to an ongoing, developmental career strategy. This proactive strategy will ensure you have options whenever you need or want a new job.

Target Companies and Evaluate Roles2 hours, 18 links

At many points throughout our lives, we decide that it’s time to find a new job and we begin to search, evaluate, and take steps to pursue specific companies and positions. The search often starts with Google or LinkedIn and a specific current or aspirational job title. There are geographic, industry or functional job boards that curate a more tailored list of roles and there are professional and personal networks too. Jobs and opportunities are more discoverable than ever. In fact, they find you! If you start searching online, you’ll begin to see ads or postings pop up wherever you go. Then, if you look at recruiters representing a particular discipline or company, you might see their name pop up in your inbox asking to connect. With so much information it should be easy to find the right opportunity. It’s not, and that’s not for lack of information or access.

The more information and choices you have in front of you, the harder it is to narrow your focus on the right opportunities. Pair information overload, inbound requests from recruiters, and jobs ads that find you with the sales and marketing messaging built into the recruiting process, and there is the chance that you’ll end up applying to, interviewing for and accepting a job that sounded great all along but is not what you’re interested in doing. I’ve seen this play out time and time again and even had it happen to me.

I thought that I was good at making decisions about my career. But as I reflected on the last couple of years, I realized I had trusted the companies and teams to do the evaluation for me. As they became more excited about my candidacy for their position and my ability to fit their needs, I became more excited. I ended up not asking the tough questions and did not orient my decision around the things that truly mattered most to me at that particular time in my life and career.

If you’re reading this, there is a good chance you’re looking for a new job or starting to interview with companies. Interviews are exciting, time-consuming, and stressful for many people. With the impact of the decisions resulting from these conversations, that’s not surprising. A significant portion of the stress is tied to the end outcome. When we put ourselves out there and find a role or company where we can see ourselves working, succeeding, and thriving, we get attached to that future version of ourselves. We start to daydream about what the new role will do for our careers, bank account, and reputation. We begin to spend time reviewing our resume, pulling up old performance reviews (“What are my strengths, really?”), and practicing responses to interview questions in front of the mirror, on our commute, or with a trusted friend or family member. As the process progresses, so does the investment we’re making in that outcome. We might start telling our friends, shopping for a new work wardrobe, even apartment hunting.

important The cost (personal, financial and otherwise) of accepting the wrong job is high. And, the prospect of finding a new job is daunting. We shouldn’t have to rely on other people’s excitement or on our own imperfect instincts—with all our blind spots and gaps in self-awareness—when making choices in our careers. Luckily, with thoughtful and diligent preparation, you won’t have to, and the entire process will be more manageable and productive. My preparation strategy will take you through a variety of specific activities and actions that build upon one another.

You’ll begin by reflecting on and designating your top priorities for your next role. Then, you’ll research roles that align with your priorities, starting with those titles and positions you’re most familiar with.

Next, you’ll broaden your search through an activity that will enable you to find roles with unexpected or unique titles that are tied to your priorities, so that you understand the full landscape of opportunities you can pursue.

Moving beyond research, you’ll analyze the job descriptions to determine which roles and companies most closely match your objectives and excite you.

Once you are familiar with the opportunities, you’ll work through a chapter and some exercises that will help you tell your career story, refine your resume, and solidify or update your priorities before you apply.

Together, these activities will help you understand how your past experiences, interests, and aspirations are connected. You’ll reconfirm the type of environments and teams that led to your most fulfilling, fun, rewarding work, as well as those experiences that you’d prefer not to encounter again. With this preparation as the foundation, you’ll be ready to articulate your accomplishments throughout the interviews and have a targeted list of questions you’ll want the interviewer to answer.

Determine Your Job Priorities

You can’t optimize for everything. It is incredibly rare for a particular job to meet or exceed all of your expectations. There are many aspects of the work experience that you will have to understand and evaluate while you are looking for a new job. Some, such as the role, your pay and benefits, and the people you’ll collaborate with on a daily basis, are easy to connect to your personal experience right away. Others, including broader company context and long-term career opportunities, may not be as tangible from the start, but may be among the most important criteria for you.

As you pursue the application and interview process, you will receive a lot of information about each of these topics. Most of the time, the messages will be subtle and embedded into a larger conversation. This is why a clear understanding of what you want to prioritize will enable you to proactively listen for signals and ask specific questions to get a comprehensive picture of how a particular opportunity aligns with what matters most to you. When your core priorities and actual work experience complement one another, you can focus on your achievement and fulfillment. However, if aspects of your work experience don’t match the factors you know are most important to your satisfaction and success, problems will emerge. Initially, the problems might be subtle frustrations. Over time, those annoyances will build and the cumulative impact of an ongoing, growing issue can become intolerable.

As you read through the priorities outlined in this section, reflect on your past experiences and take the time to complete the activity, Rank Your Top Priorities. By doing so, you’ll have clarity about what priorities you should focus on as you interview for jobs. Later, in the Ask Me This Instead section, you’ll have the chance to select questions tied to your priorities that will help you get to the heart of these matters in each of your conversations.


The combination of responsibilities and expectations that fill your days at work are what constitute the role. For many people, the role is, without a doubt, one of their top priorities in the job search. Choosing to focus on the tangible foundation of what work represents, particularly as we spend many hours of most days focused on those activities, makes sense.

So, what are the indicators that the role might be one of your top priorities?

  • This role is a critical stepping stone on a longer-term career path.

  • You are pursuing an educational certificate, degree, or training program to gain access to a specific type of role (e.g. a coding bootcamp, MBA or apprenticeship program).

  • The position represents a meaningful promotion or acceleration of your professional trajectory.

  • The way you spend your days—the activities, tools and interactions—is key to your satisfaction, productivity, or fulfillment.

  • You are making an intentional shift or pivot in a new direction.

If the bullets above resonate, focus on the following aspects of the role in your interview preparation and conversations.

First, people often think the job description is an accurate representation of the role. I’ll go into more details about job descriptions later, but for now, know that they are not as indicative of the work or experience as they should be. You will need to push to get a real, tangible view into what the day-to-day looks like. For example, it’s incredibly helpful to understand which meetings you will attend, the cadence of deadlines and how much of your time is spent in various activities. You’ll want to make sure the team can articulate these elements of the job in more depth than what is on the job description. You’ll need to ask them to show you the day-to-day experience via a glimpse into weekly calendars, reviewing agendas or letting you audit meetings. The title section of this book, Ask Me This Instead, will help you develop a list of questions to do this! If you don’t know what you’ll actually be doing, it’s hard to know if you’ll enjoy it or be successful.

important Job responsibilities are distinct from expectations, though they often get bundled together. To understand the role, you need to get clarity on the responsibilities as well as the expectations. Responsibilities are the tasks, activities, and meetings that fill your day. Expectations are the more subtle measures of success, the “how” you get the work done, the way the team wants you to show up. You could be an expert in the execution of the tasks and still not meet expectations.

Responsibilities may be metrics—quantifiable, demonstrable outcomes you need to achieve or projects and documents you need to deliver. While there might be subjectivity associated with the approach, quality, value, or impact when it comes to responsibilities, there is also a binary element that is more easy to discern. Did you reach the target numbers or submit the report on time or not?

You often find out there was an expectation when you fail to meet it. It’s the nuance—the unsaid beliefs about what really matters that will ultimately shape your experience and how people perceive your performance. These underlying expectations might include whether you answer emails or Slacks “on time,” whether you work “enough” hours, whether your attitude and presence in meetings “mesh” with the team’s, or whether you adeptly navigate office politics without ruffling feathers. The quotes are intentional. Most of the time, leaders know what they mean when they say “on time,” “enough,” and “mesh,” but they don’t communicate their expectations properly. It’s frustrating and can be the result of intentional manipulation or poor management. Either way, it’s hard to recover.

Your references can also be extremely helpful when evaluating a role and throughout the rest of the interview process. While preparing your application, ask them to review the job description and highlight examples of why they think you’ll be a strong candidate (or if they think it’s not the right next move). They will likely share insights and examples that you wouldn’t have come up with otherwise. It’s also possible that they’ll point out areas where you will need to grow and learn to fulfill the responsibilities of the position. These tips can help you proactively consider a learning plan and prioritize where you might want to proactively prepare to address questions that will come your way during interviews. The added bonus of this exercise? You’re prepping your references to have examples ready to share with hiring managers or recruiters as you get to the final stages of the process!

Spend extra effort on the questions database later in the book to hone in on getting the answers you need to these questions! If you know the responsibilities, understand the expectations and are excited to step in, work hard and live up to all those “asks,” your success will follow.

Inclusion and Belonging

Many companies are focusing more on diversity, equity, inclusion, and belonging. For individuals, the existence or absence of a feeling of belonging can transform their work experience, performance, and satisfaction. When you belong, and when you can show up as your authentic self, you are more likely to not only survive at work, but thrive. An exclusionary environment, one that denies you the opportunity to be yourself, or expects you to withhold certain parts of yourself, can chip away at your confidence, relationships, and commitment in meaningful and often painful ways. We all want to be accepted for who we are, including those aspects of our identity that are visible as well as those parts of ourselves that we hold more closely or that are not visible.

important This conversation is evolving, and thankfully, becoming one that is top of mind for leaders and businesses everywhere. As this book is being written, dynamic discussions and debates are influencing the “what”, “when” and “how,” but also the “who” and “why” for initiatives and actions tied to diversity, equity, inclusion, and belonging. The language and priorities are shifting while leaders react, respond, and commit to a path forward. In this section and throughout the book, I’ll use the abbreviation DEI for diversity, equity, and inclusion. Belonging and justice are part of the equation, though not as familiar as part of an acronym at this time. On the note of acronyms and language, different terms are used or preferred in different contexts and awareness about the nuance and significance of these terms is beneficial (find out more about exclusionary words you might come across in the hiring process here and culturally conscious identifiers here). The landscape will change by tomorrow and your own perspective may be very different from that which is presented here or elsewhere—and that’s the point! As you approach your career and find the opportunities that are right for you, your own experience and opinions and how they relate to the company and team you’re considering joining, matter.

In a contrived structure like a hiring process, it can be difficult to know when to bring your full self into the conversation and to anticipate how others will respond to what is uniquely you. Though the topic is nuanced and conversations can be difficult to initiate, it is important that you realize you have permission to ask questions and advocate for yourself. Before you’d make a decision about accepting a role, you need to understand whether or not the work environment will build you up or break you down. Your happiness and health, not to mention your success, will depend on it.

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There is a reason why “people are our greatest asset” or “the people are the best thing about working here” are quotes you often hear about the work experience. Who we spend our long days with, and how we interact, communicate and collaborate with them, are meaningful elements of our jobs. Later in the book, we’ll take a deep dive on specific people you’re likely to meet in the interview process to help you think through the importance of different relationships. This section will focus on a broader spectrum of relationship-oriented criteria, including team dynamics and leadership influence.

How do you know if people, and specifically the team dynamics and leadership influence tied to those relationships, are one of your top priorities?

  • You value and emphasize work relationships over work responsibilities.

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Offer Package

The components and value of the offer package—the salary, benefits, bonus program, stock options, vacation time, volunteer opportunities, and more—are parts of the work experience that most people can’t ignore. These are the factors that help us determine whether a particular job will enable us to live our lives. What you focus on within the offer package is highly dependent on your needs and desires.

Within the key aspects of an offer package, you might prioritize with the following in mind:

  • Are you responsible for financially supporting yourself and/or others?

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Work-Life Balance

Work, whether we want it to or not, often crosses over and impacts the rest of our life. Understanding how a prospective opportunity complements or disrupts your personal priorities and interests is necessary. The language and conversation around “work-life balance” is evolving. Depending on the path you pursue and your personal preferences, how work plays into the rest of your life—and vise versa—varies significantly. It’s also likely that what “balance” means to you will change throughout your career. At its core, work-life balance is about whether or not this particular role provides the space and flexibility for you to enjoy your life outside the office or bring parts of yourself into the office, for example, establishing friendships, celebrating holidays and heritage months, or sharing more about your weekends than commentary about the weather. Because I touch on relationships, community, and inclusion in the people, employee experience, and inclusion belonging sections, I’ll hone in on schedules, boundaries, and how to evaluate the time commitment you’re willing to give to a role.

What signals in your personal life might indicate that you’d want to focus on work-life balance in your next opportunity?

  • You have personal or family obligations.

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Career Path

Some people know early on what they hope their long-term career path will look like, or even the culminating role or accomplishment they aim to achieve. Others will find their path as they go or even explore multiple different paths while searching for the work that inspires, fulfills, or compensates them. There are many ways to move through your career. Some individuals might be focused on ascending through a particular promotion track, others might take lateral moves through different functions or departments, and some might find the role that will carry them throughout their career and stick with it. Whether you are looking to climb that career mountain, happy at the plateau, or seeking to find a role to build a home around, figuring out if your expectations are likely to be met by a particular role is beneficial.

Here are some questions to consider that might lead you to prioritize the career path available in your next role:

  • Are you intentionally looking for career advancement?

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Company Mission

Why a company exists, the problems the team is focused on solving, and the steps they’ll take to get there represent aspects of the company’s mission and goals. A company’s mission is its reason for existing. Some companies treat their mission statements like inspirational quotes about changing lives, or the world. Others are more straightforward: to provide a product or service that people need. The work that the team does, as well as the goals the business is focused on, is tied to that purpose, that reason for being. The mission, and the underlying goals and values that the company has will drive decision making, influence team structure and role design, and help shape the culture. In mission-driven organizations, the pull to participate and make a difference is a leading factor why people choose to work there and the resulting camaraderie and commitment can create a unique environment.

To determine whether or not a company’s mission and goals will rise to the top of your priority list, consider the following:

  • Are you purpose-driven when it comes to your career?

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Company Goals

Once you understand and assess the company’s mission, it’s time to understand how the organization’s goals are structured. Some companies can plan effectively multiple years out and cascade relevant information, goals, and responsibilities throughout the organization. When you’re interviewing with a company with that level of sophistication into their multi-year planning, you’ll be able to ask about their objectives and get reliable information in return. Many companies, especially early-stage startups, are still working on next week or tomorrow and the ability to pinpoint specific initiatives or outcomes multiple months or years out is… out of the question. There may be ideas or aspirations, visions, and dreams, you should explore with your interviewers, but you can’t put too much weight into information that falls into one of those categories.

The sophistication of a company’s goal-setting process, communications, and ability to cascade and distribute that information effectively throughout the organization will vary significantly. A scrappy, small company might do this well with a refined approach, accurate data, and synchronized responsibilities and cross-functional efforts. Some of the world’s top companies might be successful despite a broken or overly complicated and slow goal-setting process that is disconnected from most employees' experience. It’s valuable, if not imperative, to care about the purpose the team is working toward and understand the categories of goals they will focus on in the near term (often tied to revenue, growth, margin, client, or customer satisfaction). The “what,” “how,” “how fast” and “with whom” are the type of details that you’ll have to push to learn more about during the interview process.

With that in mind, prioritize getting a very clear picture of what’s going on right now concerning how the team operates and what they view as their organizational strengths or weaknesses during the interviews. The more you know now, if “now” sounds exciting and aligned with your aspirations, the better you can feel about “later.” If you can get behind the current initiatives and see yourself working well with the people who are on the team and find yourself curious about how a particular project might turn out, those are good signals. Perhaps that company is a place where, regardless of where they or you end up in 5–10 years, you’ll have benefited from the experience.

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Company Operations

As you search for opportunities and pick roles to pursue, another important factor to consider is where a particular company is on their journey as well as how that stage impacts the way the organization operates. The way work gets done, and the philosophy and technology that drive a company’s operations, can impact not only your day-to-day, but your overall experience and success.

In order to determine if a company’s operations supports your ability to do your best work and if that is something you want to focus on in your job search, think about these questions:

  • Is the company a brand new startup or established player?

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Company Reputation

Choosing a new role and working at a specific company has implications now, and later. There are certain companies that inspire trust, others that are recognized for their innovation, social impact, or growth, and some that are known for developing exceptional leaders across a number of disciplines. On the other hand, some companies rise and fall, are known for toxic leaders and internal strife, terrible customer experiences, or failed products, and are the subject of editorials and exposés. Some companies that have amassed billions in funding or revenue can be the same companies with bad reputations in other arenas.

The surprising reality is that companies on either end of the spectrum can offer valuable learning, growth, and opportunities, so it’s up to you to decide how the company’s reputation on different fronts will impact your decision. As you reflect, consider:

  • Do you need this role/company to be a launchpad for future opportunities?

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Employee Reviews

Before interviews, one of your primary sources for learning about employees’ experiences working at a particular company is the internet. There are endless websites with content and information including The Muse and city-focused Built In sites as well as sources for employee reviews and rankings such as Glassdoor, which can provide interesting tidbits and candid feedback. As you read through the information, try to balance it with your own real-life experience as you go through interviews as many of the inputs are anonymous and thus hard to qualify. What didn’t work for someone else, could work well for you—no two employees will have the same experience even given similar circumstances or timing at a company.

Beyond the sites we might seek out when we’re doing research, we’re inundated by messages about work everywhere we go. While scrolling through your LinkedIn feed you see updates from your network about the exciting jobs someone’s just started or the company milestones that they’re “so lucky” to be around for. Sometimes, you’ll see an intriguing headline about great perks or high salaries and click into it. It’s hard to escape. Those messages, particularly the constant flow of them, can be helpful or disruptive at different periods during our career. Those messages can also be very persuasive. When targeted by messages with positive “filters,” we’re likely to fall prey. Especially on those hard days, the days when we’re down or disappointed. The days when our boss or co-workers frustrate and exasperate us. The days when someone else gives notice, and excitedly talks about their new opportunity and we wonder, “What do they know that I don’t?” Spoiler alert—they don’t necessarily know anything more than you do.

important It’s important to read reviews and social posts with a thoughtful and objective perspective. Think about when people write reviews or share content to their social feeds. Actually, no, don’t think about people, think about yourself. When have you been moved to share your thoughts or opinions with people who you don’t know and likely won’t meet? My experience has led me to think of three primary situations when people post work-related content:

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Employee Experience

One of my least favorite questions to be asked by candidates during the interview process was some version of, “What’s the culture like at [COMPANY]?” Because I was asked this question so often, I had many handy responses to rotate through or customize to the candidate I was speaking with, but those answers were never really that great. Culture, for me, is a living, breathing experience made up of and dependent on the behaviors, words, and actions of individuals, team, and the company collectively. There can be dominant themes, and also micro-patterns, present in different pockets of the organization.

And what matters most about culture is a special combination for each and every person. I knew my answers about culture didn’t stack up to reality, but with such a generic question, I often couldn’t do much more. Eventually, I started asking a follow-up question of the candidate to ask them to specify a particular aspect of the culture that they wanted me to talk about so that I could give them information that they might actually find useful rather than a pre-packaged blurb that could have been copied/pasted at one of many different companies.

Because culture is so hard to grasp, I now focus on and emphasize the “employee experience” working somewhere rather than the culture. You can get at “an experience” in much more tangible ways through questions, conversations, and observations throughout the hiring process. They are the foundation of what you might choose to label as culture, and since that’s what I know hundreds of people have asked me about, they are the topics I want you to diligently investigate at each step of the hiring process.

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Activity: Rank Your Top Priorities

Thinking about your priorities is only the first step. To pursue them requires an extra layer of attention and intention. Putting your priorities at the foundation of your job search enables and empowers you to focus your efforts and target the roles and companies where you’re most likely to find your match.

If you do not put yourself at the center of the search, the company’s priorities will take precedence throughout your conversations and in the final outcome.

Use this section to proactively articulate what you’re prioritizing at this stage in your career. Once you write it out, you’ll find yourself evaluating everything—a job post, a benefits package, a prospective team dynamic—more confidently.

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A Job Title Is Just a Starting Point

important Titles matter so much and also not at all. During the job search, titles help you align your understanding of how your experience, career stage, and existing leveling might transition into an open role. Similarly, the titles on your resume will help others understand how they might work with you. Some companies will use industry or functional standards for their titles and others will have bespoke titles because the job doesn’t exist somewhere else. Companies may also label the same or similar work in distinct, unique, or seemingly contrary ways, even within their organization! A director at a Fortune 100 is quite senior within the organization and often deep into their career, whereas a director at a startup might run a function and have seniority within the company early on. Their experience and expertise is unlikely to be the same, though the value that each brings to their organization can be significant.

Occasionally during the recruiting process a title evolves or changes because the team learns more about what they are actually looking for and makes a more precise commitment to a level or framing. Perhaps the original title wasn’t attracting the right talent or the right talent changed the context for the role, and subsequently the best way to label it. In other scenarios, the team is testing titles—putting out the same or similar job descriptions under separate titles to see what attracts the people they’re looking to hire.

The variability, the evolution, the testing are all possible scenarios. What’s most important is for you to understand what the label represents and determine if it matches your expectations and aspirations. If the title doesn’t, but everything else lines up, it might be worth doing some research on how comparable organizations title similar roles in order to start a dialogue with the hiring team about whether a change is possible (note, I’d only do this at the late to final stages—it could be too disruptive to the process early on).

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Activity: Assess the Landscape

In order to find the right opportunities to pursue, you need to expand your search and become aware of the broader landscape of opportunities that could be available to you. This exercise will bring you from the starting point of a single title to a more comprehensive view of the type of roles that encompass the type of skills and abilities you possess (with any number of different titles!).

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Activity: Create a Personal CRM

Don’t just search for jobs, look for people and keep track of them!

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Break Down a Job Description

The truth behind most job descriptions is that they are lightly edited, kind of plagiarized, branded marketing documents with a lot of words that often don’t say that much. Once hiring managers know they have an opening, they think of the most common label that exists that represents the position they have in mind and put it into a search engine. This results in a bunch of job descriptions from other companies. With all these examples, they begin to skim them and pull out the “best parts,” copying them into a document before massaging them into a more coherent and relevant version to post (or simply doing a “find and replace” for the other company and substituting their own). Oh, and they try to make it sound fun and compelling (you’ll learn, you’ll make a difference, we’re changing the world, and free beer on Fridays!). They do their best to make this job, this work, this grind, sound appealing or at least more appealing than the grind that you know or that other companies might be offering.

It’s almost impossible to encapsulate the experience of a job in a short list of bullets, even if you start from scratch. Because of that, most job descriptions are also too long—both in the list of responsibilities you’ll have and the qualifications you’re supposed to bring. And yet, when we’re searching for a job we tend to believe them. It’s magical thinking. One way to ground yourself in this reality is to stop everything you are doing right now and look at your company’s careers page. Do the job descriptions sound like they represent the work and environment that you experience every day?

Although job descriptions might try to make it seem otherwise, there are few truly original jobs. You might have had this realization while searching and comparing titles. Because the job description as a “tool” is so broken, you have to look beyond, dig deeper, and discover what is actually going on for this position and within this company. To do this, you need to break down a couple job descriptions.

Activity: Break Down a Job Description

Once you have found several postings that you’re drawn to, pick two to break down. This will help on multiple fronts. First, it’ll help you more quickly and critically evaluate job descriptions. It will also help you tailor your application materials and will kickstart your reflection on your experience in anticipation of interviews. Remember, you may not be able to check off every line of the job description, and that’s OK!

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Write a Resume That Tells Your Career Story24 minutes, 4 links

Once you think you’ve found the job you want, it’s time to move to the next step—preparing to apply and interview. Yes, preparing. If you have really found the job you want, don’t send off a resume on an impulse! Time is of the essence, but sending off an incomplete or rushed resume or application could shut the door now, and for future opportunities. Once you have your target roles and companies, it’s time to build your collateral. For now, a resume and LinkedIn profile are still part of that solution. The flaws of the job description are mirrored by those we all put into our own marketing documents—our resumes. Truthfully, the resume is a relic that definitely needs to be innovated. We spend countless hours writing bullets that make sense to us but that might not connect with anyone else. We curate a document that highlights what we think are our top or most impressive accomplishments, but that might not reflect our real capabilities or our interests. We edit the statements over and over for space, change the vocabulary so much so that often what we end up with is a list of generic jargon.

important Just because the resume structure is outdated doesn’t mean your experience isn’t compelling, or that your passions and what you want to learn aren’t important when seeking a new opportunity. My approach to building out your resume will help you see your experience holistically to bring out the best of what you’ve accomplished. It’ll take extra work—more than dusting off the last version and adding some new bullets. In fact, you’re going to start thinking about your resume as a story. Perhaps you haven’t thought about your resume as a story before. But if you take a storytelling approach to reflecting on your experience before you craft a document, you will unlock a more interesting and comprehensive version of your experience. As an added benefit, thinking through the events, people, and context is valuable interview prep as it enables you to add more nuance and depth to your responses.

To start, you’re going to begin to view yourself as the central character on a journey with heroes and villains, struggles and successes, learnings and legacies. This exercise will help make this process less of a task… you might actually enjoy it (maybe just a little bit).

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Identify Your Main Characters

  • The Protagonist. You! This story is about what you want and need—a new job. Your resume needs to include the information that puts you on the best path to get to your end destination. Think through the moments you’re most proud of, the feedback you’ve received, the contributions, and impact you’ve made in each of your roles, and what you’ve learned.

  • Other Primary Characters. Along the way, you’ve worked with and met people who have influenced your story and success. Understanding their influence as well as thinking about the context of your relationships will unlock plot points you might not have previously considered adding to your resume. What type of characters should you think about?

    • The Heroes. There are surely people who have inspired you, pulled you along and served as role models throughout your career. You may envy their abilities at the start, until you realize the hero will help you see your potential and achieve it. Whom have you admired, who shined the light on your capabilities and cleared the path for you?

    • The Villains. Every now and then, you encounter someone who makes work harder, frustrates and exasperates you and seems to find joy in crushing your spirit, productivity, or results. There are important insights to be garnered from your experience with villains that may represent some huge lesson, impact, and growth in your career. We often tend to put these experiences aside, but I recommend you evaluate them closely to see what positive results came out of them (especially as there will be a lot of interview questions that you can connect back to these experiences!).

    • The Crew, Squad, or Posse. When have you been better because you were together? Thinking about the people who were by your side during periods of peak performance or intense creative collaboration as well as the day-to-day will lead you to remember moments and challenges that you wouldn’t recall if you were only thinking about yourself.

    • The Teacher. Hopefully you’ve had a manager, mentor, or colleague who took you under their wing and accelerated your ability to be effective in a given role. Think about people from across the companies you worked with who opened your mind about new ways to solve problems or who pushed you to gain the skills you needed to progress and advance.

    • The Protégés. As you have developed expertise and experience, who did you support along the way? How have you built stronger peers or direct reports by stepping in and stepping up to support collective outcomes? When did your insight or contribution change the way others approached a problem or project?

Like in any good story, characters may switch between roles as they learn, grow, and evolve… or devolve. I’ve had villains become valuable members of my crew and heroes fall to the dark side. Those can be particularly engaging stories to consider as you think about what interactions created the most growth or led to the most important professional relationships and experiences. You’ll have the chance to workshop your resume at the end of this section and in the workbook.

Consider the Place and Time

The setting, or place and time, are often included on a resume without much extra thought—this role was at that company, located in this city. Seems simple enough, right? In the most basic sense, that is the setting. However, now is the time to start to think about setting more broadly, specifically where the companies you worked at were in time and place, that influenced your experience. How you operate in a well-established company with hundreds of people is dramatically different than a high-growth startup. The distance the company traveled while you were there impacts your role and responsibilities and contextualizes why you might have pursued a specific path or hit certain roadblocks during your tenure. The more you can connect dots and make your experience come to life in relevant and specific ways, the more the hiring team will be able to assess if your skills and capabilities will be effective in their environment.

As you consider the setting, ask yourself about the situations below to reflect on how they might have evolved during your time in a particular position. This will surface new awareness about how you changed and grew in response to the world around you. With the context fresh in your mind, you might see the events and accomplishments through a new lens and with more clarity about the impact, reasoning behind, or significance of a particular experience.

Examples of Place or TimePrompts to Consider How the Setting Impacted You
Strong economy vs. recessionWere you able to choose the job you wanted, or did you have to take the job that was available? Did you have part-time or contract roles rather than a full-time, regular position? Did your trajectory (title or pay) flatten or slow down? Did you have to take a role outside your preferred industry or function? Did the company have layoffs or did your compensation and/or benefits decrease?
LocationWere you in a role at a company’s headquarters or a smaller satellite? Were you in a city where there was a density of talent to hire and a strong team to work with and learn from? Were you in a larger city or market with diverse industries and opportunities that you could access or were there limits? How did a remote-first or distributed team structure impact your experience in previous roles?
Company success or failureWere there periods of rapid growth (hiring) or contraction (layoffs, turnover) that impacted you? Did the company raise venture capital or go through a merger or acquisition? Did the company have a competitive advantage, was it disrupting an industry or fading out of relevancy? Were there news stories or features about the company, its leadership or products? Were these stories positive or negative? Was the company meeting or exceeding goals or missing expectations? Was there steady and consistent leadership or new executives stepping in and changing the course?
Your own place and timeDid you have a well-defined role or did you “wear many hats?”Were there training programs available or did you have to drive your own development? Were you just starting out in your career, hitting your stride, or angling for the next step? Was work a priority or were you more focused on other aspects of your life?

Map Out Pivotal Moments

Your career, like a plot, is made up of a series of events. There are events of a more significant magnitude—new jobs and promotions, for example. Then there are those that may seem small, but that are, upon reflection, deeply meaningful and important—perhaps that first tough conversation with a direct report or turning a bad relationship around.

Though time facilitates a natural sequence and order of the events that take place, it may not always be the most compelling way to tell your story, specifically within the context of a particular role or period of time. The moments that are most relevant, impactful, and indicative of the journey you’ve been on as the protagonist might need to be put into a structure that will catch attention, build suspense (OK, probably more like interest in this scenario) and keep the reader curious and wondering about what they will read next.

Start to think about events, accomplishments, and activities that were important to you at the various stages and steps of your career and that would be interesting to the reader (like a recruiter assessing your potential, a hiring manager wondering if you’ve got the capabilities, or a future direct report trying to see if you’re someone they think they’ll learn a lot from).

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Include Tension and Conflict

The desire to move beyond and even forget particular conflicts we have throughout our careers is natural. However, conflict in your career, like the tension in a story, is where some of the most interesting and important moments occur. In fact, these moments often represent the catalyst for characters to transform. Being able to articulate how these tests impacted you will add depth, interest, and a dose of reality to your resume. Without realizing it, you’re also preparing for the interviews by thinking about the experiences that pushed you and those that you might want to avoid in the future. These memories can be helpful in building the list of questions you’ll ask certain interviewers.

Interpersonal conflictConsider a broader lens
Relationships that got off to a bad start that ultimately turned aroundExternal factors that shifted timelines, product design, or even internal operations
The dynamics in meetings during periods of stress or high stakesWhen a customer backed out of a deal or a colleague unexpectedly left the team
Trust, or rather the lack thereof, within a team or organizationHard moments, unexpected changes, or big surprises
Failure that led you to quit, change course, fire someoneTimes when you made a mistake or intentionally disrupted progress
The times you cried or lost your temperA moment or experience that was embarrassing
Tough conversationsA period when you were bored or unengaged in your work
New hire or new manager changing the status quoWhen you didn’t believe in the company, its product, or people
Moments that made you look for another roleLack of a feeling of belonging, being “othered,” or needing to assimilate

As you reflect, acknowledge the frustration, pain, and problems, and the context that surrounded them. Then, think about what positive growth, lesson, or change happened as a result. That is where the magic lies and what will be most helpful as you craft your resume, prepare to respond to interview questions, and evaluate if you’d encounter similar challenges in a new role.

Connect Your Story to Their Needs

One of the reasons I recommend taking the storytelling approach to updating your resume is that it helps you think about your journey and accomplishments in a new light. When confronted with a blank document, the pressure to put the “right” examples down is real and there is a tendency to fall into self-doubt. This can result in bullets that are bland (when you’re writing something to fill space) or even untruthful (when you don’t think a particular bullet is strong enough so you modify the details to sound more impressive). Then, because many people write resumes in isolation without feedback from those who worked with them or know them well in a professional capacity, resumes often fail to capture the reader’s attention—and that’s the entire point! Recruiters and hiring teams want to connect dots quickly between candidates and their role. Think about what they are looking for and how you can specifically and clearly connect your experience to their needs.

important If time and capacity were unlimited, resumes should be customized to a specific company and role. Because that level of tailoring often requires more time than you have available, consider developing one or two versions, each emphasizing a unique angle on a potential company’s needs. For example, you might be open to manager and individual contributor roles. Consider framing one resume about management and leadership, going deep into your ability to get results through others via coaching, delegation and feedback. For the other version, you could focus on the depth of your expertise, technical or functional accomplishments, and examples of your ability to collaborate.

Or, let’s say you are applying to a Fortune 500 company and a Series A startup. For the Fortune 500 company, you might choose to include more information about your cross-functional talents, project management capabilities, and communication skills. For the version you’d submit to the startup, you’d highlight examples of your flexibility and resilience, when you delivered results under pressure, and your ability to take on new and diverse challenges.

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Activity: Translate Your Story Into a Compelling Resume

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Activity: Connect Your Story to the Roles You Want

It’s time to bring together all the previous activities, align your experience to key themes, and then select the most compelling examples of your experience to highlight under each role as you pull everything together into a resume.

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Activity: Pair Your Resume with a Cover Letter

Cover letters are one of the aspects of the application process that cause a lot of angst, confusion, and frustration. Candidates wonder if the hiring team even reads them or if the time they spent is wasted. While I cannot vouch for every company’s application review process or every hiring manager’s approach, when I’m recruiting I open the cover letters attached to applications as often as possible. I find they give new insight and add breadth and depth to the resume bullets, which are often generic. Though I cannot guarantee that everyone, or even someone, at the company will read your cover letter, refining your thinking and how you articulate your experience, readiness, and alignment with the requirements of the role is additional practice and preparation for you.

A well-written cover letter is a short, to-the-point pitch about why you are the candidate for this job. It should add something new about your experience and abilities to the application—building upon rather than restating what is in your resume. If you cannot customize your resume to every position, you must tailor your cover letter! To miss the chance to bridge your list of accomplishments and skills with their opportunity and highlight why you chose this position over others out there might mean you don’t get to interview.

You don’t have to overthink or spend hours crafting your cover letter. Building upon the framework below enables you to complement the information presented on your resume, customize the application to the company, and highlight some of what makes you a great candidate.

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People and Power in the Interview Processan hour, 1 links

The interview process is often just a few hours spread over several days or weeks. That is not a lot of time to get to know the company, responsibilities, and expectations, let alone all the people. You’re going to spend 40+ hours a week over the course of many months or years working with these individuals. It’s important to recognize each person’s unique contribution to the process, work, and your experience. The people you spend your days with can transform the mundane into meaningful or turn a dream job into a toxic, miserable slog. Your interviewees are a small representation of the company in most cases (unless you’re interviewing at a tiny company or new startup) and your time with them is your primary chance to get a window into the broader employee and team experience.

Throughout a standard interview process, you’ll encounter a handful of prospective colleagues. Some of these interviewers could play a key role in your experience and others you will just know in passing, but they are all valuable guides to your future work experience. Each person brings a different lens to the company, role, and team and can unlock new perspectives and information that others wouldn’t be able to share. Crafting a targeted set of questions for each interviewer profile that addresses specific areas of interest based on your established priorities will help ensure you efficiently and effectively gather information.

To get the best 360° view of the company, you’ll need to take advantage of the opportunity to ask a tailored set of questions to each person. In this section, I’ll explore the roles, personas and priorities of the people commonly involved in the interview process so that you can incorporate them into the plan you create later in this book. Some sections are more expansive than others—these are people who are more pivotal and influential in the recruiting process. For example, the recruiter is someone you’ll almost always interact with, and the hiring manager is probably the most important person for you to get to know. In some cases, a single person can play more than one of the roles outlined, which is why it’s so important for you to know who you are interviewing with, why, and what their role will be in the process. Remember that titles or roles do not always equate to influence or trust within the hiring team—anyone participating in the process could be the key vote or veto in interviews. Make sure you take an inclusive approach to engage with each one of your interviewers. Later, in the question section of the book, you’ll see questions designed for each of these personas so that you can create your specific interview plan.


Put simply, the recruiter is your guide throughout the process. Often the first person you talk to, the recruiter wants you to succeed. This is both a positive and complicated reality as they have diverse motivations to consider throughout the process including, but not limited to, those of the hiring team, those of the candidate, and their own.

This is not a game of love, but there are parallels. Recruiters play the role of matchmaker. Recruiters spend time networking and interacting with lots of different people at any given time including hiring managers, candidates, external partners or agencies, cross-functional interviewers, and executives, and are constantly trying to understand, manage, and meet their varied expectations for the role, hiring process, and the eventual new hire.

They fulfill this responsibility with a combination of intuition, judgment, and influence. Even when someone (either an internal team member or a prospective employee) is being transparent and direct, there are “unsaid truths” that a recruiter has to reflect upon and process within the bigger picture. A talented recruiter is always listening, as they work to understand a broad set of factors to see where and how they will converge toward the desired outcome—getting the right person in the right role as quickly and efficiently as possible. Typically, recruiters are natural conversationalists and make that initial conversation relatively easy for candidates by conveying information, enthusiasm, and support.

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important Put simply, a great manager can transform your career while you work with them and long after. Finding that kind of manager is magic and worth several percentage points on top of any salary. They influence so many aspects of your experience day-to-day and over time. As for the bad manager, think back on the vent sessions you’ve been a part of with team members, partners, and friends. What is one of the aspects of the work experience that everyone bemoans the most? Their boss. As a recruiter, I know this is one of the things candidates need to focus on the most throughout the hiring and decision-making process.

During the interview process, managers play the role of mentor, motivator, and evaluator. Their accomplishments and experience at work depend largely on the strength of their team. If anyone is more motivated than the candidate to find the right hire, it’s the manager. In navigating the interviews, the manager must weigh the capabilities and experience of the candidate within their understanding of the work to be done as well as how this prospective hire will complement and extend the expertise and output of the rest of the team.

While they may seem to be all-knowing or all-powerful in the process, in most cases, the manager will not be. There will be other voices represented in the process, other interviewers for example, as well as other decision-makers, such as their boss or a more senior executive.

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Department Executive or the Boss’ Boss

Depending on the nature of the company, role, and makeup of the hiring team, you may or may not encounter the hiring manager’s boss or a department executive. Even if you do not meet them, understanding their role and influence in the hiring process and your ultimate path at the company is valuable information to gather during interviews.

Put simply, this leader is responsible for the hiring manager’s team’s success and likely a broader scope of work. With this bird’s eye view, they want to ensure there are capable, engaged, and talented individuals in each position and, importantly, that those individuals come together to form a high performing and productive unit working toward a collective set of priorities. The department executive is tasked with operationalizing a higher-level set of functional or company priorities and building an organization (vs. a team) that delivers. As with the hiring manager’s motivations, a strong group of teams reporting to an executive enables and impacts their success so their attention and commitment to the process takes into consideration the full team’s performance, capabilities, and expertise.

In most cases, the leader will have collaborated on, reviewed, or approved the job description. Depending on the size of the company or the seniority of the role, they may have weighed in on the content of the job description, as they help drive and delegate priorities and goals for the overall team. Typically more tenured in their career (though not always), a department executive will have institutional, industry, and team context that enables them to interview and evaluate with confidence and a perspective that is long-term and beyond the scope of many of the other interviewers. At the same time, they remain close enough to the details and day-to-day operations that they can credibly determine an individual candidate’s strengths and gaps while calibrating and comparing those attributes across their teams.

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Activity: Craft Your Interview Elevator Pitch

The elevator pitch—what you say when you have 30 seconds to make an impression—is a great tool in the job seeker’s toolkit. The elevator pitch can be used in passing at a networking event, or to kick off an interview with someone who may not be as close to the role or hiring process (like an executive). As you refine your job search to a specific type of role or company, having this quick pitch ready is in your best interest. (Having it ready means you’ve practiced actually giving it!)

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Elevator Pitch Example

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Activity: Craft a Thank-You Note

If you want to get the most out of the effort you put into your elevator pitch, consider incorporating a very similar structure into your post-interview thank-you notes (or more likely, emails). It’s not required to send a follow-up and it can even be controversial—after all, the company is looking for someone to fill their position, maybe they should send you a thank-you for coming in! But, if you view the follow-up note as a chance to highlight your candidacy, build a relationship with someone who could be a team member—now, or down the road—and to re-connect dots between your conversations and potential to contribute based on your post-interview reflection, taking a few minutes to send these notes can be worthwhile.

The most efficient way to do this is to add a personal sentence or two at the start of the elevator pitch structure highlighting why you enjoyed meeting a particular interviewer and an insight you took out of the conversation.

A Thank-You Note Example

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CEO, Founder, or Other C-Level Exec

Put simply, a chance to talk with someone in this position is incredibly valuable and they may play a variety of different roles during the hiring process. In smaller-stage companies or roles in their direct reporting lines, they may be evaluating you based on functional, industry or technical expertise, leadership potential, or a wide set of competencies and capabilities they believe are key to success in the particular role, and also within the overall organization. It’s possible that they are close to the operations of a given team, project, or position, but don’t expect them to spend time getting into the weeds and don’t take them there with your questions (but do ask questions!).

If you’re interviewing at a large company or in an entry to mid-level role, you may not interview with the CEO. However, if you’re pursuing a role at a small company or startup, there’s a decent chance you’ll be able to cross paths during the hiring process with the CEO, a member of the founding team, or another C-level executive. Regardless of the company size, C-level leaders and founding teams have to operate at the 50,000-foot view, bringing together diverse topics, priorities, people, and processes into a cohesive, structured, and viable path forward. In some ways, these senior leaders are accountable to “no one” (they don’t have a boss), but they are also accountable to everyone (the full team, investors or board members, customers, shareholders and beyond).

In an ideal world, there is alignment from the leadership team all the way throughout and across the organization. In reality, that’s tough, so focus less attention on the specifics of the position and listen to their insight on themes, long-term priorities, and aspirations for the team and company to get an impression of how their leadership flows throughout the organization. In anticipation of this conversation, refine your elevator pitch and do extra research on the company and the leader’s background (by reading blog posts or articles, listening to podcasts, following them on social media, and watching interviews). During interviews, be prepared to speak not only to your own background and experience but a set of connected and expanded topics as well. This is a rare chance to demonstrate your presence, articulate your talents, and leave a lasting impression.

Peer or Team Member

There is a good chance you’ll get to meet someone during the process who would be a peer on the specific team you’d join. This conversation can be a powerful glimpse into an important business relationship, and the information you’ll gather from the interview as well as the questions that a peer might ask will illuminate critical elements of the role. Put simply, prospective peers are often closest to the details of the work to be done, understand the status, challenges and opportunities, and what it takes to be successful relative to the goals the team is responsible for achieving. They might also have a similar background or set of skills and capabilities and therefore ask very targeted or specific questions to evaluate your expertise and determine if you have the qualifications to meet the expectations of the role and work well with the team.

During the interview, they may play the role of a companion or partner that would be a trusted collaborator on projects and someone who will bring internal insight and context to support your integration and success. It’s also possible that they will take a more competitive approach and step into the interviewer role as someone who is not necessarily a judge (they are not the hiring manager), but also not a friend. They may challenge you subtly or directly to test the boundaries of this potential relationship while weighing the trade-offs of how you might make their life better or potentially worse.

In an ideal world, people in these roles want nothing more than a super talented, smart, capable team member to work at their side, but others will be threatened if they believe you will outshine them, “take away” something they enjoy doing, or upset a status quo that works for them.

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Cross-Functional Colleague

A strong company is rarely built in silos with a narrow group of functional experts driving the process or product development from end-to-end. With that in mind, most hiring managers will include relevant cross-functional team members in the hiring process. Cross-functional team members will be key contributors to company initiatives that are complex and large-scale, with dependencies rooted on the team and associated with responsibilities listed in the job description of the position you are targeting.

Put simply, both in the interviews and on the ground, cross-functional team members play the role of the translator—bringing their expertise and skills to bridge the gaps, add value and get stuff done. It’s because of cross-functional collaboration that work happens, that connections, barriers, or breaks get identified, and that collective success is possible. Being able to effectively navigate the distance between different teams and disciplines, as well as find the commonalities to move quickly and productively through problems and toward big picture goals, is helpful for the candidates and hiring team alike.

Because of these factors, the cross-functional team member may serve as an astute judge for a specific set of your skills and capabilities, or might provide a more general read on how they believe you will collaborate, communicate, and contribute to relevant initiatives.

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Human Resources (HR)

Put simply, HR helps shape the employee experience via compensation, benefits and administration, talent development and training, and cultural programs, and are called upon to solve other people’s problems. They aim to design with all team members in mind while keeping an eye out for consistency, fairness, and legal requirements, balancing their responsibility to the company and its employees.

Depending on the environment and your own experience, HR might be a team that you trust and value and that you see as a partner and advisor, or you may view them as a cumbersome administrative function that complicates what should be simple and reduces what is actually complex to an annoying form or checklist. In fact, these are two of the more positive views into the role that HR plays in organizations. In some companies, and for many people, HR enforces outdated policies and the law, serves to protect the company rather than support the employees, and caters to those who do wrong rather than those who have been wronged. Pair that with the perception that HR doesn’t have a real seat at the table, takes a resource-focused versus human-oriented approach to problem solving, and fails to innovate or adapt to an ever-changing workplace—it’s not surprising that seeing a HR team member on your interview list may not excite you.

As someone who has had roles within this function in startups and established companies, I’ve seen the positive and negative impacts of what these teams and individuals can do. I often talk about how I think the function is desperately in need of dramatic change and do my best to support innovation and the infusion of new ideas as part of this transformation. 2020, and the layered impacts of a pandemic with its health and remote work implications (childcare, technology, and more!), reckoning with racial injustice, and layoffs, furloughs, and economic recession have further tested the HR function. With these acknowledgments and my personal beliefs, and despite my passion and intentions, I know I have also missed team members’ expectations before. I see these challenges and look back on my own experiences as an ever-present chance to learn more, do more, and grow in my expertise and capabilities. I, like many HR professionals, come into the function because they care about making the work experience better and want to do it for people, with people. Sometimes broader company policies, hierarchy, access to information, or legal requirements interfere with HR’s ability to take what would be the best, most efficient and practical path. Additionally, an abundance of employee questions and concerns can take up more time than the innovative culture-building activities that may have inspired them to get into the field.

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Direct Report

When you’re interviewing for a managerial or leadership position, you’ll want to learn about the dynamics of the team situation you’ll be stepping into. Early in the process, start to flesh out the overall picture:

  • What is the size of the team?

  • Who are the team members?

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How Companies Learn About You Outside the Interview Process

The concept of a back-channel may or may not be as familiar depending on how often you’ve been part of interview teams or interviewed yourself.

Put simply, “back-channel” refers to the conversations prospective employers might have with people who know or have worked with you that you have not proactively shared as references. These conversations can happen at any stage of the hiring process, from before they get on the phone to after an offer has been extended. Often companies take this approach to get the “real” story about you, as your official references are most certainly enthusiastic champions—and prepared ones at that! Like references, back-channel conversations are most often used to complement and validate existing beliefs about a particular candidate (mostly positive) and rarely change the course of the process entirely (though, it can happen) so don’t beware these conversations, but be aware that they might occur.

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Ask Me This Instead1 links

Imagine wrapping up final interviews with a company knowing that you not only had the chance to share your story and skills, but that you gathered all the information you could about the company, team, and role in order to understand whether this is the right opportunity for you. Asking focused questions connected to your personal priorities is empowering and builds your confidence at each step of the process, especially when you need to determine whether to accept an offer.

If you want that feeling, it’s time to design a 360° strategy for your interviews. Building your plan will enable you to get the most out of the process, just like structured interviews help interviewers achieve their objectives. Asking targeted questions around your priorities to specific people will make the conversations more illuminating and productive. And, candidates who ask the best questions stand out.

This section of the book exists to help you create the plan and take action to make your interviews work for you. As you dig into the question database, you’ll find a common question paired with insights about why it will not get you the information you need. Each of the common questions is then reframed with what you can ask instead, and highlights about why that framing will unlock valuable details about the role, team, and company. This is a chance to bring your voice and power into the process and builds upon the content and exercises from the previous sections of the book. I have aligned questions by persona and topic as a starting point. I encourage you to think about what questions you need to ask and who is the right person for you to ask them to—you may align the questions differently!

Ask Me This Instead Question Database

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Activity: Build Your 360° Interview Plan

Find the activity in this Google Doc!

Warning Signs in Interviews9 minutes

As you progress through the interview process, you’ll get unique thoughts and opinions about aspects of the role, its purpose, and what the person who will step into the position will be responsible for achieving from each interviewer. If the interviewers are in general alignment—that is, they have a defined set of clear talking points and their answers are complementary rather than tangential—that’s great! You will be able to focus on resolving the differences around the edges or get valuable insight into where potential friction or disagreement might emerge should you join the team.

Unfortunately, not every interview team is aligned. While it may be hard to get visibility as an outsider looking in, if you’re aware of some of the dynamics that interviewers may be dealing with among themselves or within the organization, you can pick up on clues to read the room and identify warning signs more effectively. As you go through each conversation, take in the information provided by each interviewer as well as your gut reaction to what you’re observing and learning. These tangible insights and instincts can help drive your lines of questioning as you progress, or influence your decision to continue in the interview process or bow out.

Is the Hiring Team in Agreement on Why the Role Is Open?

A role often gets posted when someone who has been doing that work leaves, when a new initiative is launched or when there is a gap or pain point that needs to be addressed and no one internally has the ability or capacity to solve it effectively. There are other reasons why new roles come into being, but those are by far the most frequent.

In early conversations with the recruiter and hiring manager, ask questions to understand why this position is open. As you continue through the interview process, pay attention to what other team members share to see if they continue to reinforce or contradict what you’ve already heard. Gaps in alignment may seem inconsequential. However, they have the potential to grow and complicate working relationships and outcomes over time. Understanding if everyone agrees on the need for the role and how the position’s responsibilities will be integrated to complement and strengthen existing efforts is key.

dangerWarning Signs!

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Is There Clarity on the Responsibilities for the Role?

For there to be clarity on responsibilities, whether a backfill or new position, the hiring manager would need to assess relevant changes to the business and how those might impact the profile of talent, goals, or requirements associated with the position. It’s the combination of reflection, forward-thinking evaluation and effective communication to the hiring team that will lead to a consistent view into the role and set an interview process up for success. To do this requires extra work. Often, the hiring manager doesn’t have the ability to reflect and assess thoroughly so the burden to connect what you are seeing and hearing is your responsibility.

dangerWarning Signs!

  • The way the interviewers describe the work does not align with what is outlined in the job description. Do the interviews add new responsibilities into the mix or talk about an entirely different type of work? It’s possible that, depending on their own role, people will highlight and focus on different things so be cognizant of the nature and significance of the gaps.

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Is the Hiring Team Invested in Your Success?

Often the person writing the job description and crafting the expectations has a credible understanding of what needs to be done, the skills required, and how the role fits into the broader context or team. Perhaps they have done similar work themselves or managed a team with similar positions and goals. If this is the case for the role you’re interviewing for, it will be to your advantage. However, it is possible that the hiring manager is scoping a role that is distant from their own expertise and experience. In this scenario, there is a chance that, despite their best intentions, they miss the mark on defining the work and aligning the requirements to specific skills, capabilities, and knowledge and may not be as targeted or effective in screening candidates at every stage of the interview process.

dangerWarning Signs!

  • There is a significant disconnect between the title and responsibilities. For example, they are hiring a “Director,” but the responsibilities represent those typically fulfilled by entry-level positions or use terms and descriptions that don’t quite align with what you’d expect to see in that position.

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Developmental Career Strategy18 minutes, 6 links

By this point, you’ve put in a tremendous amount of thought and preparation into getting the best outcome from the interview process, which gives you a meaningful advantage relative to other candidates. You have done more in that effort than the large majority of candidates ever will, and you’ll be better off in your next job and throughout your career because of it.

Hiring is hard and companies have an advantage. They know the pool of candidates they are working with, they can click through resumes, peruse LinkedIn, and control the flow of the process while they decide who is the “best.” They have the chance to test, compare, and see how everything settles. Hiring teams get to ask, ask, and ask some more. Then, at some point, they make a decision. If it’s an offer, they push, nudge, and smile to get you to accept and join on their timeline, and with their terms.

Companies often talk about hiring the “best people.” Realistically, teams hire the right person to do the work well enough, and who is also interested, available, and known to the company. I realize this is less impressive from an ego perspective and less punchy as an employment brand headline, but it’s closer to the truth. Someone can be the right hire in one environment—succeeding, thriving, and delivering impact all day, every day—and fail in another environment. It’s the mutual match that matters.

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Take Power in the Process

Now, I want to remind you of your power in this process so you can seize your potential.

  • When you know and commit to your priorities, you have power. With reflection and preparation, you’re going to hone in on what is most important to you as you go through the job search and interview process. Then, when you’re in the interview room, you can focus on being authentically you. If you feel yourself putting on an act, projecting something that is not naturally you, or compromising on one of your priorities, beware! Think of the effort it’ll take to sustain and maintain energy, engagement, and commitment to the work if you’ve made compromises on the things that matter most.

  • When you have a plan, you have power. You might have wondered while reading why you should take all these steps to prepare for your interviews and might still be doubtful about your intent to follow through. Having a plan gives you power; you aren’t only subject to the company’s process but can take steps to ensure that your priorities are covered as well. When you walk in with a plan, you can maximize the limited amount of time you have with each interviewer and target your follow-up on the most important items. Getting to interview for a job you’re really excited about is hard enough. If you don’t know what you want out of the process, you’ll miss the opportunity to get the job that could be right for you.

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Nurture Your Network

You should start looking for a job long before you’re ready to apply or make the move. This is the interviewing equivalent of “always be closing.” You should “always be looking.” To do this successfully, you need to find credible websites that focus on the roles and companies that are most in line with your interests (for example, B Work for mission-driven job seekers, Jopwell for Black, Latinx, and Native American students and professionals, or FlexJobs for remote or work-from-home roles). To find these niche boards, pair a role or function, for example “design” with the words “job board” and you’ll quickly discover sites like Dribbble or Behance. These are not the big job search engine sites. Those sites, including LinkedIn or Indeed, can be helpful when you know precisely what you’re searching for and want to see what openings might be available within your geographic area or search criteria. Next, you should subscribe to newsletters or updates that you can consume on your own timeline (or when an interesting subject line catches your eye) and that include reliable highlights about leaders challenging the status quo, companies making a difference, or products that are changing the way people perceive, experience, or spend their money within a particular space.

Even if you do not want to have a prolific voice on social media, establishing a presence by following interesting people who comment on relevant topics, have roles that you’d aspire to have or who surface articles, podcasts, or posts that intrigue you is beneficial. “Using Twitter,” by Fadeke Adegbuyi provides expert advice on how to use Twitter to find a job (including those that are never posted!), build your network, and advance your career. This is important to start and sustain before you need a job, you never know when you might hear or find something worth pursuing!

important You should also cultivate and invest in your network on an ongoing basis. Your LinkedIn connections are only valuable if you can activate them (i.e. get a response when you reach out)! One strategy is to organize your connections into three groups.

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Interview, Interview, Interview

You build on your power and seize your potential when you interview every chance you get. To the job of your dreams, you have to show up at your best. You don’t show up at your best without practicing. I want you to interview every chance you get, or at least every year.

important Why should you look elsewhere when you have a job you like? It’s the best way to make sure you are there for the right reasons—engaged, enthusiastic, and all-in. Thinking clearly about your career path and preparing to succeed in interviews is more easily approached when you’re not under the pressure of needing a new paycheck, and when you have the chance to weigh your current role’s pros and cons relative to any move you’d consider making. This provocative approach to interviewing opens the door for honest reflection throughout your career. It gives you the freedom to see what else is out there and determine if what you have is better than other options available. You can explore and have conversations to learn more about yourself and how a role and company can support your interests and priorities. It also helps you understand how your experience and skills are valued in the marketplace, which can help you negotiate an offer or go back to your company and ask for a raise. These realizations unlock something powerful—you have options.

If you keep your skills fresh, do your best in the role and cultivate relationships with current, former, and prospective colleagues, you won’t be stuck. So, even when you love your job, answer recruiters’ emails and apply for jobs that look amazing. Sometimes these efforts will go nowhere. Other times, they’ll yield worthwhile conversations and new insights. And maybe, they’ll end up pointing you to the next best opportunity for you—one that you wouldn’t have found without looking at your career as a journey with multiple destinations and a variety of ways to get from here to there.

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Get Ready to Run

So how do you know if you’ve found the “one”—the job that’s right for you, right now? You should answer one of my favorite questions to ask candidates for yourself. I like to close final round interviews by asking, “What would make you run toward this opportunity with enthusiasm and what would make you run away?

I give this advice because, though I have asked this exact question dozens of times to others, I didn’t ask it to myself a few years ago. While working long hours in a demanding job, I found myself daydreaming about quitting during the day and casually scrolling through job postings or venting about my job to friends in the evenings. Though I couldn’t see it and truly didn’t realize it, I was already running away. So, when a compelling opportunity with awesome people came up, I took it. It was, objectively, a great job, but it wasn’t the right job for me. Had I taken the time to evaluate my priorities, explore what options were out there—and crucially, had I asked better questions of my interviewers—I could have saved myself and a team I cared about a lot of time, effort and… emotional turmoil. Look, this type of thing happens, and it’s not necessarily anyone’s fault, but the work and approach outlined in this book can save you and others from having to have the same experience I had.

It is best to intentionally move toward a new role rather than leave a job for any role other than your current position. As an interviewer, the “run toward” question gave me some of the best clues and cues about what mattered to the candidate, where their mind was, and what our risks were if we wanted to hire them and bring them onto the team. I knew it was getting at something when I started to see how people reacted to the question. It often made them sit back, smile, and genuinely reflect before they answered.

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