Debug your design interview journey

In the year since I started mentoring folks on Merit, I’ve gotten a lot of questions that go something like this:

I have been actively interviewing for long enough time that I feel like I should have an offer, but nothing has materialized yet. What am I missing?

When someone asks me this, it’s a sign we need to debug their interviewing journey. Debugging is an important part of building products, and it’s just as important to use that iterative lens on your own job-seeking efforts. Many of the people I talk to are not tracking their job applications, have not considered the point where they commonly fall off the rails, and are struggling to figure out how to improve.

If you’re going to get a job, especially in a tough economy, you’ve got to apply design thinking to your employment search. How might we turn the distressing process of finding a job into something we can learn from? Let’s start with one of my favorite design artifacts: a journey map!

Design interviewing is usually broken up into four types of activities:

If you start to track your process according to these stages, you’ll recognize patterns. This is similar to how teams begin to notice patterns when they track and analyze usage data for their products. You can build a job search dataset with a Kanban board in a product like Notion, Figma, Trello, or Asana. There are many templates out there already, but here’s mine if you’d like to use the exact one I did to complete my two most recent job searches.

I'm going to walk through each stage in this article. I have many thoughts, so this is going to a be long post — but the job hunting process is long and arduous. You deserve every word. But if you want to read a step-by-step version, you can find that on my website. I have additional resources at the bottom of this post, too.

Now let's jump in!

Stage 1: Application

Before you start meeting members of the hiring team at your future employer, you’ve got to get noticed by them. This requires you to either submit your information to an online form or get referred by someone who works at the company. I’ve applied to countless jobs throughout my life. If things go well, it’s usually quite straightforward: you submit your résumé and portfolio, then you hear back from a recruiter within a week or two.

If you’re not getting bites at this stage, it might be because you need to seek out more direct referrals. Cold applications are a dime a dozen. Hiring managers don’t have the energy to wade through hundreds of applications, and referrals always get prioritized over manual submissions.

Let’s talk about how to get more referrals!

Building a referral pipeline

To get referrals, you’ll need to reduce the degrees of separation between you and the people who work where you want to work. Your likelihood of moving to the next stage depends on who recommends you. Here’s my personal hierarchy, based on quality and impact:

Tier 1: Former coworkers

The highest-quality referrers worked directly with you at a former employer and can attest to your experience. These people will have major sway with the hiring manager because they know what it’s like to be on a team with you. If their experience with you was very positive, they’ll even reach out to advocate on your behalf and help move your interview process along!

If you have any relevant experience in the field, you’ve gotta try to get recommendations from people you worked with. Maybe you’ve only done an internship. You could have a few freelance projects under your belt — or perhaps you’re more experienced with full-time roles. Reach out! Former coworkers and collaborators can have a huge impact on your future employment endeavors.

Tier 2: Friends and family

Next is someone who knows you fairly well (say, a friend or family member). While they likely can’t speak to your work experience, these people know you on a human level and might be able to influence on your behalf. Even if they don’t know what you’re like at a day job, they’ll definitely put a good word in for you.

Tier 3: Friends of friends

These folks are people you’ve met once or twice through friends. Or maybe you mentioned you’re looking for a job and a friend offered to connect you to someone else they know. These loose connections are wonderful to have, but the quality of the referral will be lower. For example, they likely won’t advocate for you with the hiring team because they don’t know you very well.

Tier 4: Social media connections

Maybe you met a nice person at an event in 2018 and connected with them here on LinkedIn. You haven’t spoken to them since. Now, they’ve posted an interesting role and you’d like to reach out for a referral! Be warned: social media connections are the loosest, and you should avoid asking them for much.

If your social media presence is well-curated and you have a fair amount of clout, you might organically get referrals from social media connections. However, most people who barely know you and only have your internet presence to go by wouldn’t refer you outright. I recommend getting on a video call before asking for a referral. Otherwise, this person won’t be able to vouch for you.

Getting referrals

Make a habit of searching for connections at potential employers before submitting an application. If you have multiple connections, use the aforementioned tier system to prioritize your contacts. Reach out to the highest-quality connection, ask to catch up if you haven’t talked in a while, and offer them the potential for a sweet referral bonus from their employer.

Newer to the industry? Or, maybe you didn’t have great previous employment experiences? It’s time to build your network by meeting more people. Attend local meetups, join some online events, or just chat with cool folks on a social media network.

Here are just a few examples of communities you can join:

• Merit - connect 1:1 with design mentors
• UXDX - A free Slack community and design conference
• Design Operations Assembly - A design community for education, jobs, mentoring, networking, and more
• DesignX - A Slack community that also hosts various events
• Design.Systems - A group of design systems practitioners

There are loads of communities and meetups out there, I know and putting yourself out there can be scary. But humans are often quite friendly and usually want you to succeed. Don’t be afraid to make genuine connections!

Troubleshooting the application stage

If you’ve gotten referrals and are still not getting to the screening stage, something else is up. You may need to modify your portfolio, for example. Are you showing your process or just the prettiest final mockups? Design leaders want to understand how you work, and that means not being afraid to show early thinking.

Your résumé could need tweaking. Is the layout easy to scan? Are the descriptions of your role easy to scan? Did you ship a project and forget to include post-launch stats? Employers do actually read this stuff, and design leaders have high expectations for the legibility of a designer’s résumé.

Perhaps the issue is more logistical. Did you forget to send the password to your portfolio along with your application? Are you password-protecting content that’s already been released to the public? These little details add friction, and most employers won’t put in an effort to overcome them before rejecting you.

Or, maybe the issue is that you don’t have enough recent work. Strengthen your portfolio by doing a few freelance, volunteer, or personal side projects — for example: a hackathon, nonprofit, local store, or that business idea you’ve been mulling over for a long time. Please avoid speculative redesigns of popular products, as they’re usually quite corny. Employers want to see work that is grounded in reality (even if it didn’t get shipped).

If your application meets all the criteria outlined in the job description and you got a referral, you’re almost a shoe-in to get to the next stage. Unless someone else got in before you and received an offer first. It’s brutal out here. 🥲

Stage 2: Screening

After you submit your application for a role, the hiring team must evaluate and narrow down the pool of interested talent. Candidates who are noted to be a good fit on paper will be invited to schedule a time to speak with someone at the company. This is usually done by either a recruiter assigned to the role, the hiring manager, or an IC designer.

If you make it to this stage, congratulations! You’re being screened. Now that you have a foot in the door, you’ve got to kick it wide open.

What to expect

Most screening calls are relatively short; you can generally expect to be done in 30 minutes. The agenda is usually as follows:

• Introductions (who you are, how you got into design, what you’re excited about)
• An explanation of the role
• Questions from the screener (how you think, past projects, relevant experience)
• Questions from you to the screener about the position
• Wrap up (next steps)

Preparing to be screened

Avoid going into a screening call without doing some prep work. Outline your talking points—what the person should take away from your conversation—and practice them until they feel natural. Many people swear by the STAR framework for talking about past projects since it focuses on problem-solving and impact. How might you integrate that framework into your storytelling?

A great screen interview will feel like a friendly, two-way conversation. Bad ones feel like interrogations, and you might even leave the call with a weird vibe. The goal is to make sure both you and the hiring team are excited to move forward, so trust your gut if something feels off (especially if you spoke directly with the hiring manager).

Some companies require multiple phone screens before moving to the onsite phase. For example, I’ve spoken to a recruiter, then an IC designer, and then the hiring manager in one screening loop. The first person you speak with should explain the company’s interview process while talking to you live, and you may also receive a timeline via email.

All in all, screening calls are an energy check. Even in a competitive market, you should be able to move forward if you can:

• Be respectful to the person you’re speaking with
• Confidently talk through your career highlights
• Clearly discuss your design process
• Show why you’re a great fit for the role

But sometimes you might find yourself constantly getting rejected after screening interviews. Not sure what’s going wrong? Time to debug!

Debugging the screening phase

If you don’t get moved from screening calls to an onsite, the person you spoke to likely didn’t see you as a good fit for the role. There are many reasons why that might be the case. Let’s dig into some of the most common ones!

Show your interest

Some interviewers may reject you due to bad chemistry. Maybe they thought you weren’t engaged, or maybe something you said didn’t hit the mark. Sometimes this can veer into discriminatory territory — especially for neurodivergent folks.

You shouldn’t need to be a manic pixie or corporate cheerleader to get hired. But showing interest in the role and the company can affect interviewers’ perception of you. So, let’s talk about ways you can show interest while still being you!

If you struggle to explain why you want to work at a specific company, you might need to clarify your own goals more. Try writing down qualities you want your next job to have. If the company or team you want to join has any of those qualities, you can reference them in the conversation.

Reviewing the job description and company career page can also give you fodder for topics to discuss on the call. For example, I might bring up a project that matches requirements in the job description. If the company’s business model has an impact on how design works at the company, I might also mention that. Or, maybe I’ll ask how the vision shared in a recent blog post might affect plans for the design team.

It’s a bit corny, but people appreciate the engagement. That being said, sometimes you do the best you can to show interest and still get rejected. Maybe the company culture would’ve been a bad fit and you dodged a bullet!

Learn to talk about yourself

Interviews are not normal conversations. You are fully allowed—encouraged, even—to humble brag in an interview. If this sounds intimidating, you likely need to improve at talking about yourself confidently.

You don’t have to be a jerk; no one wants to work with someone who puts others down! But you do need to show self-awareness, pride, and an interest in your career path. After all, if you’re not excited about yourself and your work, why would the hiring manager advocate for you?

It’s unfortunate to say, but presence does make an impact. Try writing 5–10 bullet points that walk through your career history highlights, then practice talking about them out loud until you sound natural. The added composure you’ll get from some practice can go a long way.

Focus on clarity

The person you’re speaking to doesn’t have the time or energy to look for reasons you might be the best fit. Many interviewers need to be spoon-fed what you might think is obvious! Show them how everything connects and you’ll have a strong chance of moving to the next stage.

Read through the job description before every call and identify any potential matches with your work experience. Practice explaining how past projects and employers, even if tangential, can be tied to your potential at the company. This was especially helpful for me when I switched industries—there were some surprising parallels between music streaming and eCommerce, for example!

Lots of interviewing advice talks about this already, but I’ll mention it here too: please make your contributions to a project as clear as possible. If you didn’t work on something alone, it’s okay to give credit to your collaborators as well! But your impact is what employers care about; don’t let that information get lost in an attempt to be humble.

Show your best work

If you do go through designs during a screening call, try to show the best match for the employer you’re talking to. And just like with the application process, don’t be afraid to show messy thinking. This is your chance to show what an amazing problem solver and member of the team you’ll be!

One common issue with design share-outs at this stage is a lack of attention to detail. Please use spell check and ensure you won’t be surprised by the contents of your presentation. It should be the best representation of your work possible.

Navigating pay talk

Sometimes recruiters will sneak in a question about your expected salary range. This question doesn’t benefit you at all. It helps them narrow the pool down to whom they perceive as more affordable candidates.

This practice is going out of fashion since it can reinforce pay discrimination, and it’s also illegal in certain US states. You don’t have to directly answer this question. And recruiters should know not to ask—it’s a huge red flag!

The company should have salary bands in their job description. If they don’t and a recruiter starts a discussion about pay during your screening call, turn the tables on them. Ask them about their design career ladder and pay bands.

If they keep digging (another red flag), say you expect to be compensated at the level that is commensurate with your years of experience. Never say a number before the offer stage.

Stage 3: Onsite

The onsite is the most crucial stage of the interview process. It’s an exhausting gauntlet — a consecutive series of 30–60-minute interviews with IC designers, your future manager, and other relevant stakeholders. If you’re lucky, you can do this process remotely. And if you’re really lucky, you can spread the process over multiple different days.

I'm going to share onsite stage thoughts from a variety of perspectives. I've presented in and sat through many onsite interviews myself. I've also given a lot of advice in mentorship calls — and I've had many conversations with peers about the subject. Let's talk about the onsite interview process and cover common reasons designers get rejected.

What happens at an onsite?

Onsite design interviews aim to assess the candidate’s design chops, problem-solving skills, and potential value to the organization. Usually, you will start by presenting select work to the hiring panel for 60 minutes. The work you present depends on the company; sometimes you’ll share two past projects of your choice, while other companies might ask you to prepare the solution to a design challenge.

After the group presentation, you’ll likely have a series of chats with different people who are honestly just trying to vibe-check you. If you’ve got a spicy company, you’ll probably also be asked to do a whiteboard exercise. When a hiring team is really trying to test your commitment, they will make you meet random people whom you may never actually collaborate with.

Debugging rejection after onsites

There are a variety of reasons for dropoff at the onsite stage. Some of them are outside of your control:

• Another candidate was a perfect fit
• The company did not care enough to remove bias from the hiring process
• The hiring team didn’t know what they wanted when they put out the original job description, and they decided they wanted something else after speaking with you

All of these outcomes are unfortunate and unfulfilling but ultimately have nothing to do with you. There are other reasons for dropoff at this phase, though, and you can change how you operate based on them. I’ll walk through each so you can bring your best self to the onsite boss battle.

They made you do a design challenge and didn’t see what they wanted

Let me start by saying: design challenges are a huge red flag. Most designers — even the entry-level ones! — already have a portfolio of work and can choose a few projects to talk through. Take-home challenges are a treasure trove of biases (for example, folks with more privilege can afford to spend more time on them).

Some companies require this step because they believe it’s the best way to analyze a person’s thinking. I personally think that’s incorrect and have avoided opportunities that require me to do extra work I don’t have time for. If you can afford to be choosy, I would encourage you to only complete a design challenge if you really like the company.

Now, let’s talk about what can go wrong here. The hiring team usually has a rubric of solutions along with details to look out for during the presentation. When you complete the challenge, the team will usually grade your response according to these pre-set expectations.

The issues with design challenges usually boil down to not having had enough time to deliver the outcome they want. Maybe they didn’t like the lack of consideration for customer insights, or it could’ve been that there were glaring holes in your process. But this is a hypothetical (and probably unpaid) project — it was kind of you to even spend time on it!

I usually don’t take design challenge rejections personally, and I’d recommend you don’t either. You probably dodged a bullet.

Unclear portfolio presentation

There are various ways in which your portfolio presentation could result in a rejection. It could be too high-level — this is likely the case if interviewers keep asking for more details. Can you edit your presentation to proactively answer their questions?

Your presentation could also be too in-depth. If you often run out of time before covering everything, have to speak quickly, or can’t take questions from the team, you need to cut some content. Try writing a 1-sentence summary describing what interviewers should leave the room thinking, then rearchitect your presentation to tell that story. Anything that doesn’t fit the narrative must go.

It’s also possible that your presentation is disorganized. If you find yourself tripping over content in your deck, you need to edit the parts where you stumbled. Your presentation should flow seamlessly, and you should never have to answer retroactive questions about the timeline of your work.

Finally, maybe the team couldn’t understand much about you from your presentation. A lot of companies run on vibes, so hiring managers want to know what value you’ll add to the business and the team. How can you make your presentation an expression of yourself? Have fun with it — the team does want to connect with you.

Collaborators didn’t get a good signal

After the group presentation, you’ll likely have several solo conversations with your future colleagues. If your portfolio presentation went smoothly, you may have stumbled in a 1:1 interview. Think about the experience; did you struggle to answer any particular questions?

Common missing signals include:

• Unsure if they can be a partner to Product Management
• Couldn’t tell how well they work with Engineering
• Unclear if they have experience with UX Research or Data Science
• Little to no mention of design systems

Each of these issues can be resolved by preparing to speak in detail about how you collaborate with others. Experienced designers can speak about past situations where they’ve worked on a product team, conducted user research, or contributed to a design system. If you don’t have past experience, you can talk about your ideal process and reference techniques you may have learned from resourcees such as books or blogs.

If you look at the job description again, you might also find more clues. Most hiring teams are looking to check off as many boxes from the job description as possible. If you go into future 1:1 interviews with the role requirements at the top of your mind, you can do a better job of explaining why you’re a good fit.

They made you do a whiteboard challenge and didn’t see what they wanted

One unique type of collaborator interviews might also be a “whiteboarding” challenge. The goal of these sessions is to understand how you plan your work, ideate in an innovative way, and (maybe) deliver solutions under time constraints. Sometimes these challenges are quite opaque, but there are some threads I’ve noticed across whiteboard interviews.

Here are some reasons your whiteboarding partner may have declined to hire you:

• Jumped into solutions too quickly
• Didn’t ask for or reference user insights
• Thought process was not structured and the facilitator had to step in too often (”not senior enough”)
• Solution was uninspiring

Whiteboarding challenges are stressful and uncomfortable, especially at first! It’s very normal to forget some steps or flub when adrenaline runs high. Be patient with yourself, remember to breathe, and always start by making a plan.

Get some whiteboarding practice with 60-minute design prompts of your own. Redesign a kiosk for your local transit system, create a new TV remote, or design an SMS-only system — these are three real challenges I’ve been asked to solve. If you’d like a book full of examples, check out Solving Product Design Exercises by Artiom Dashinsky.

Similar to take-home challenges, whiteboarding challenges are a design culture red flag. At best, whiteboard sessions give you a chance to bond with your future coworkers. At worst, they are an easy way for you to do unpaid work. Once again, you may have dodged a bullet if this was the reason for your rejection.

Concern about culture-add or values-fit

The last and hopefully least likely scenario is that the team is concerned about how you might impact the team dynamics. This is not about culture-fit — hiring teams should not look for what they already have. Instead, I’m specifically speaking about a company’s values, the way people work, and the effect new hires can have.

Hiring teams often look for people who will amplify their values. While every company has different values, you can usually expect them to include respect, accountability, and a customer focus. Consider ways to show you’d be a positive addition to the company’s culture. For instance, if a company had a value of collaboration, I might research new collaboration techniques and share examples of what I’d like to try next.

Sometimes the issue can be that a past workplace or academic culture has negatively impacted your conduct; an example of this might be a gatekeeping-heavy environment. If you find yourself bringing negative energy into interviews, you might need to undo past workplace trauma. I’d recommend reflecting on past experiences, defining your ideal company culture, and creating commitments as an individual in the workplace. You might need to work with a mentor or coach on improving this, as it can be hard to recognize and unlearn toxic behaviors by yourself.

One warning: please avoid faking for the sake of sounding more hireable! Anything you do in this regard should be genuine since you’ll be expected to bring the same mindset to the job. If you change your personality once you start a new role, the average employer would catch on quite quickly and let you go.

Stage 4: Offer

The offer stage is the final moment in the hiring process. You’ll first receive a verbal offer, which may include their intent to hire you and a breakdown of your proposed pay. The company will send you a contract to sign once you hash out details like your salary and start date.

This is an awesome moment. Congratulations! However, mishaps can still add friction to the beginning of your new chapter. Offers get rescinded for various reasons, and the practice has become increasingly common.

While I hope you’ll never have to worry about an exploding offer, it’s good to be prepared. Let’s talk through common reasons offers fall through and how to avoid them.

Salary expectations were mismatched

Companies and individuals often have very different expectations around pay. At this stage, you should be able to negotiate your salary or other forms of compensation such as a hiring bonus. While you should make it to a signed offer, you could still drop off if negotiations stall.

The best way to avoid getting rejected during the offer stage due to mismatched expectations is to communicate your needs before you get too far into the process. Nowadays, recruiters fully expect candidates to ask about pay during the initial stages. Corporate salary transparency is also required in many parts of the USA and has gained traction around the world.

Determine your income requirements before getting too deep into a job search. Consider your monthly bills, debt totals, and savings goals. This will help you find your minimum.

Once you have a minimum, you should check how that lines up with the industry. Don’t accidentally undervalue your work! Use sites like Glassdoor and levels.fyi to see if you need to inflate or shrink your expectations. Ideally, your required salary will be well-researched and therefore quite reasonable.

To be clear: I'm not saying you need to give your number before the offer stage. However, you should know — and be happy with — the company's intended budget for the role. If you wait until the offer stage to discuss their number, you might be disappointed.

Checks didn’t pass

Many companies perform reference and background checks that can impact the status of your pending employment. These kinds of frustrating, anxiety-inducing checks often come from a place of privilege and introduce bias. Companies assume that one’s past experiences reflect who they are at the moment — and who they’ll be in the future.

While you can’t control a lot of this process, you can certainly make a positive impact with your selection of references. Choose them wisely: a good reference has personally worked with you and is your biggest fan. A bad reference feels neutral about you at best. The worst is someone you didn’t have a good relationship with or someone you didn’t collaborate with professionally.

Contact your references in advance to confirm their availability and feelings about your time working together. Check what they plan to say about their experience working with you. This will help you present the best version of yourself to the hiring team.

Sometimes employers want to hear from your most recent manager, not just peers. If you didn’t have a good working relationship with that person, it might be worth following up with your future manager to see if anyone else can give them the same insight. We’ve all had a bad management experience before, and it shouldn’t stop you from finding your next role!

Internal org changes

The last bucket of issues is organizational. There are several ways that an organization’s changes can lead to the deletion of your role. Any of them can happen during the weeks between your accepted offer and the first day of employment.

Budget cuts

Corporate mismanagement and lack of planning can result in your role being made redundant. The only way to avoid this issue is to assess the likelihood that your future employer will need to lay people off. While any company can decide to do layoffs for any reason, cash-negative operations are at a higher risk of triggering surprise mass departures.

Check out details about their business model. If the company is public or planning to IPO soon, you should also be able to search for documentation of their income in quarterly profit and loss reports or SEC form S-1. Ask the hiring team questions about profitability and runway; it’s quite common to discuss the potential for layoffs since they’re everywhere.

The work you were going to do no longer exists

Major re-orgs, which can happen up to several times per year at some companies, can cause roles to change or disappear. In my experience, corporate restructuring usually results from a change in strategy, leadership departure, or both at the same time. Re-orgs are more likely to happen at the beginning or end of a fiscal year. If you’re lucky, you’ll still have a job but potentially a new team or manager.

Agencies can also have short-notice reductions in workload due to changing client needs. When I worked at a consulting company, we had constant fluctuations that impacted our need for full-time support. I once had to push back a contractor’s start date because their planned workload suddenly disappeared; luckily, I was able to find additional work for them with another client in just a few days.

These situations are challenging to predict. The most you can do is consult the hiring team about your future employer’s strategy. And if the company is an agency, you can dig into more detail about their client workload.

That’s it!

As someone who went through the gauntlet at the beginning of this year and came out only slightly scathed, I empathize with everyone who is looking for a new gig right now. It’s a rough economy, but you’ve gotta believe in yourself and your worth. I hope this advice helps.

Other resources

Looking for more job seeking tools? Below are some resources I and others have used in the past to improve the chances of getting a new job. I hope they help you, too.

• Resume Worded - AI-powered tool that gives you feedback about your résumé.
• Merit - Mentorship platform where you can connect with folks and have them review your work.
• Pearl - Connects hiring teams with diverse and vetted jobseekers.
• Ask a Manager job search posts - Get advice directly from a hiring manager.
• Per My Last Email podcast - A podcast by two leadership coaches that occasionally covers job search topics.
• Happen to Your Career podcast - A career change podcast for people who don’t want to settle.
• Design Life podcast - A podcast about design and side projects for motivated creators that sometimes covers career transitions.

Best of luck to you on your journey! I wish you all the success in the world. Got questions? Grab time with me on Merit when I'm available.