Learning From Rejection

14 minutes


Updated October 11, 2023
Land Your Dream Design Job

You’re reading an excerpt of Land Your Dream Design Job, a book by Dan Shilov. Filled with hard-won, personal insights, it is a comprehensive guide to landing a product design role in a startup, agency, or tech company, and covers the entire design interview process from beginning to end, for experienced and aspriring designers. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, commentary and future updates, and a high-quality PDF download.

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

Figure: A Generic, Cryptic Email

You might get this generic, cryptic email. 🤔

It’s easy to blame yourself and feel terrible as your thoughts race to think of what you did wrong. Before you get caught up, I would encourage you to take a deep breath and step back.

important You can choose your reaction. If your friend went through a similar situation, how would you talk to them about it? Approach yourself the same way—self-compassion helps you take the learning in and bounce back stronger.

In this section I’ll cover why candidates get rejected. Think of failure as a stepping stone—use it to improve your chances of success next time.

important Rejection along your interviewing journey is inevitable. It means you’re pushing yourself and not settling. How you handle it determines where you ultimately end up.

First Step—Ask for Feedback

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

Here’s a general template to follow:

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  1. Thank them for giving their time.

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

  3. Ask for feedback. You’d like to improve and it would be helpful to know about your growth areas so that you can be an even stronger candidate the next time around.

  4. Close by thanking them again for the opportunity.

Companies are hesitant to share feedback. In short, it might expose them to litigation if the candidate feels they’ve been rejected unjustly due to discrimination. Unfortunately this incentivizes most companies to avoid feedback altogether.

Most of the time, you might get a carefully worded response mentioning an area of concern in no specific terms. You’ll need to read between the lines here. For example, if the recruiter said your soft skills need work—think of how you presented yourself or how you came across. It may be beneficial to cross-reference this feedback by asking a current or former colleague for their (radically honest) assessment.

The granularity of feedback will vary from nonexistent to vague, but even then I would still encourage you to ask for it as it may uncover your blind spots—mistakes that you’re completely unaware of.

Framework for Working Through Feedback

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

Figure: Breaking Feedback Down

Break the feedback down into quadrants.

Another way to prioritize is looking at feedback through a dual lens of effort and control. Obviously, high-leverage actions need to be done first, but on the flip side, let go of things that you can’t control—no need to stress out about things that can’t be changed.

Reasons for Rejection

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

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

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

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

This question usually breaks the wall and allows the interviewer to communicate what they’ve seen so far. Then you act on this feedback immediately and set the right impression.

Let’s look at a couple more factors that are in your control that you can use to your advantage.

Interview Performance

Even after having prepared and practiced ahead of time, you will still make some mistakes during interviews. That’s OK. Things don’t always go according to plan, so it’s important to take the new learning in. If you haven’t already done the post-interview retro, I recommend you start there.

You might discover areas that you want to practice or improve upon, such as the whiteboard exercise or the app critique.

While this book gives you a structure that you can take and adapt, I also recommend practicing with a design friend. This will help you see past your own blind spots and open up new perspectives.

You find and win a great job against a pool of very competitive candidates who may want that job as much, if not more, than you do.Debbie Millman

Interviewing can feel like hard, thankless work. If you’re good at your work, shouldn’t they just hire you already? The truth is, even in our current age of design abundance, competition is high. So don’t forget to practice and put your best self forward.

Few “Real-World” Projects

Design is a hands-on discipline—the closer you can get to tangible results in practice, the more convincing your argument to employers that you can do the work. In other words, the more “real” your work is (getting a product fully built, shipped, iterated upon), the more prepared you’ll be, compared to “simulated” work environments (for example, only working with other designers on static mocks).

Figure: Spectrum of Design Project Types

Based on your current experience, where in this spectrum do your projects fall?

If you’re new to the field, getting the first job will be hard, as employers might feel like they’re taking a bet on you. But you can alleviate their worries by showing proof that you’ve done this work before. My recommendation is to look at internships, side projects, open source projects, or hackathons—to name a few. If real-world experience is a barrier, continue filling your portfolio, showing that you’re serious about your craft.

Years of Design Experience

Even if you have the “real world” experience… you might not have enough. Everyone wants a senior designer with at least three-plus years of experience. But how do you get experience without experience? The reality is that most design jobs don’t need a senior designer—mid-level or even entry-level designers can hit the ground running and deliver impact.

Figure: Unrealistic Design Job Requirements

These design requirements are getting out of control…

Dig deeper behind the title. What are the responsibilities, what kind of experience are they looking for? Can you deliver on these expectations or rise to the occasion? You can address the experience gap with examples that show how you were able to transfer your skills to solve increasingly complex challenges.

Companies aren’t looking for someone with five-plus years of experience anyway. “X number of years” is shorthand for someone who’s done the work, has experienced different environments, and is able to do the work without supervision. You can get that experience in two years, depending on where you work. Or you might stagnate and not reach a level of proficiency even in ten years—be careful where you work and which environment you choose.

Lack of a Specific Skill

Sometimes you might get rejected due to a lack of a certain skill or the company’s need at this time; for example, they’re strong in UX but need more visual designers. If so, this is an opportunity to get better at a specific aspect of your craft. However, maybe you also don’t care about this skill (visual design, for instance), and if that’s the case, you might look at opportunities where you can play more to your strengths while finding resources to help you level up your growth areas.

Domain Experience

Sometimes companies may hesitate to bring on designers who don’t have deep domain expertise. For instance, your experience is in enterprise design, but they want consumer designers. Or a company may want someone with an intimate knowledge of the entertainment space, but you don’t have that experience. As a result, these companies may discount your non-domain experience heavily.

The thinking goes, if this designer hasn’t done the same thing elsewhere, they won’t be a good fit here. Nothing could be further from the truth. Design is a fluid discipline. Some designers prefer to specialize in one domain, but many also expand and grow their skills in different industries.

storyDuring one interview, I was preparing for my next stage, when I got a call a day before saying it would be a waste of time for both parties if I showed up because they didn’t think I had the skills necessary. The reason? They wanted designers with more consumer experience. This didn’t stop me from getting consumer design offers elsewhere. So don’t let one rejection deter you from applying to roles that may seem like a stretch.

So what does this mean for you? Have the conversation with your interviewers, show examples of where you transferred your learning successfully. These could be different domains (for example, consumer to enterprise), different platforms (web to mobile), or even different design disciplines (from graphic to service design).


Occasionally you might price yourself out of the market. When it comes to salary, recruiters ask about this question up-front, usually during the phone screen.

There are a few ways you can answer this, but it helps to do your research up-front from multiple sources, such as LinkedIn, Hired, or AngelList, to get a realistic estimate of what you’re worth and how much you should be thinking about as far as base compensation is concerned (especially when you’re applying to startups who compensate heavily with equity).

Ultimately, it’s a personal question. Sometimes it’s worth it to sacrifice higher pay for learning. Ideally you can be in a role that gives you maximum learning and compensation, but that’s not always possible.

Factors Outside of Your Control

Not everything is under our control. Sometimes the role might get closed due to budgets or other issues.

storyIn one of my roles, after I gave a two-month notice, I started looking for a replacement by posting on job boards and going to design events. I found someone who not only had more experience but also had deep domain expertise. She interviewed for the job and things went well. Unfortunately, the role was later cut. It happens. You may be the ideal candidate the company isn’t ready for.

Alternatively, a company might be in a low design maturity state. Your skills might not be valued enough or the role is scoped down tightly. In that case, the rejection may be in your favor, as it allows you to pursue better opportunities where design is valued more.

importantDesigners have more power than they realize. Yes, the field is competitive. Yes, there are many designers out there and, according to the latest #designtwitter, everyone is a designer. But many jobs also go unfilled. Certain markets and metro areas have more roles than designers. To paraphrase William Gibson, we live in the age of design abundance, but the roles are not yet evenly distributed.

Some Rejection Is Healthy

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

What to Do When You Get the Offer14 minutes

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

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

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

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