Interviewing your UX interviewer

Jeremy Bird
11 min readJan 23, 2020

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Employees sitting holding papers with question marks over their faces

You’ve been there. We all have. You have just spent an hour being interrogated on everything from your design approach and defending design decisions to explaining the short stints on your resume. You’ve had to explain what you consider “innovative design” to be and critique the company’s existing products with little to no context. You’ve been asked to detail why they should hire you and been judged on “culture fit” at every turn. You’ve told the same stories multiple times and even dealt with passive-aggressive interview tactics designed to see how you’ll react under pressure.

Then your interviewer turns to you and asks:
“What questions do you have for us?”

While it may be true that the interviewer questions to candidate questions ratio is often drastically one-sided (which is a whole other topic entirely), it is absolutely essential that candidates come with questions they have prepared beforehand. Why? Well beyond the fact that it’s much easier and much less stressful, when someone asks you what questions you have for them, that too is a test. I once learned (months after the fact) that the #1 deciding factor on why I was hired for a UX Design role over the competition was that I asked the interviewers what they considered to be very insightful questions. They could tell that I could interview as well as be interviewed. They assumed that if I could ask good questions of them and get to important insights in a job interview, that I could do the same with their users in user research interviews. I am not alone. I know many designers who were selected based on their question-asking skills (and probably hundreds more who aren’t aware that was why they were hired).

In the same way asking all candidates the same questions is important to evaluate each one fairly and as objectively as possible, having a prepared list of questions to ask interviewers helps candidates be deliberate and consistent in the way they evaluate one company against another.

And, of course, most importantly, asking great questions helps you come off confident and experienced and stand out from the pack in the best possible way.

Types of questions

When asked what questions they have for the interviewer, I’ve observed many candidates fall into the pitfall of asking the same, boring, common questions just about everyone asks without much preparation. You know the ones:

  • How much does this position pay?
  • What is the culture like?
  • Who would I be reporting to?
  • How big is the team?
  • Etc.

While knowing the answers to these is important, wasting your limited question-asking time asking these types of questions to the hiring manager or potential co-workers, can be a major missed opportunity and makes you come across as one of the pack. Usually these types of questions will either become obvious without asking, or you can follow up with a recruiter about them after the fact.

Insightful Questions

To really stand out you need to catch the interviewer off guard. Give them a question or two that makes them really think. Whenever I hear, “Wow I’ve never been asked that before” or “Great question, let me think about that for a minute”, I know I have struck gold. A couple examples of questions in this category are:

  • If you could wave a magic wand and magically solve anything, what would it be?
  • What keeps you challenged here?
  • When was the last time you celebrated something as a team? Why?
  • Imagine a dream day here. Everything goes right and works smoothly. You’re in a state of flow and have a big smile on your face. Walk me through that. What is the biggest leap of faith in that description?

Naturally, what qualifies as “insightful” will depend on the company, position, interviewer, and how the interview has gone so far, but preparing questions ahead of time can help.

Probing Questions

Another great category of questions are those that probe for insights that you want to know, but can’t just come out and ask. We all want to know about the culture, for example, but usually get really canned responses if you flat out ask about it. Another example is most designers want to know if teams are focused on outputs or outcomes, but if you flat out ask it that way I’ve found that you get idealistic answers, rather than honest ones. Instead, ask questions like:

  • When was the last time you celebrated something as a team? Why?
  • What was your last big “failure” and how did the company react? What did you learn?
  • What is ____________’s ‘why’ for existing?
  • Etc.

Evaluative Questions

One of the most important factors in considering a new opportunity is your future manager. Are they knowledgable? Does their management style match how you like to work? Is this someone you can learn from and that will invest in you? To find those types of insights, I like to ask simple questions designed to evaluate the level (and kind) of experience the manager and team has. I was told once by a senior leader that “You shouldn’t spend one minute working for a manager who doesn’t inspire you and help you to do your best work.” I couldn’t agree more.

The purpose of asking the following questions isn’t so much a pass/fail as much as it is to gather information that will allow me to make a decision with both eyes open. No company, manager, or employee is a “perfect” fit, but asking evaluative questions can help you find a manager who can really help bring out your best and help you grow according to whatever “growth” means for you.

Some examples of these types of questions are:

  • What do you see the main difference to be between a graphic designer and a UX Designer?
  • How do you judge when someone is ready for a [insert next level for you] level role?
  • What have you done to create an environment where innovation can thrive?
  • Etc.

Story-based questions

Just like with user research, the best kinds of questions by far are those that get the interviewer telling stories. Not only is it more enjoyable and memorable to hear stories, but you can gather much from a simple story. You will know you’ve done well with your “asking questions” task if you can get the interviewer to start telling you stories.

Some examples of questions that can encourage story-telling are:

  • What’s the last time you really saw your company culture shine?
  • Imagine a dream day here. Everything goes right and works smoothly. You’re in a state of flow and have a big smile on your face. Walk me through that. What is the biggest leap of faith in that description?
  • Tell me about a project you worked on in the last 6 months (who proposed it, how was it prioritized, what challenges came up, what would you have changed)
  • What have you done to create an environment where innovation can thrive?
  • Etc.

Non-verbal questions

It is also important to come prepared with a list of questions to which you want answers, but which you (hopefully) won’t actually need to ask. This helps you focus your attention on what you really need to know to make an informed decision on if the role and company are a good fit for what you’re looking for. If you can’t get answers during the course of the interview, these can also make good follow up questions later on via email to keep the conversation going and stay top of mind to the recruiter and hiring manager.

Some examples include:

  • How does the company measure success?
  • What is the structure of cross-functional teams?
  • What kind of budget exists for software, onsite research, & ongoing learning?
  • What software or technology does the company use (design, collaboration, backend, front-end, deployment, etc)?
  • Etc.

Example questions

Now with the types of questions in mind, I would like to share my list of go to questions that I have found useful in the hundreds of interviews I’ve participated in (both as a candidate and hiring manager). This is by no means a conclusive list, but it is my hope that these questions might serve as a starting point to help you be better prepared to stand out in your next design interview when asked to ask questions.

(The list is sorted by category to make them easier to skim through when I’m in an interview.)

BOSS

  • What’s your management philosophy?
  • What keeps you up at night?
  • If you could wave a magic wand and magically solve anything, what would it be?
  • What do you see the difference to be between a graphic designer and a UX Designer (product designer)
  • What keeps you challenged here?
  • How has the company helped you achieve your career goals?

CULTURE / STRATEGY

  • What is the vision or direction of the company for the next 2 years?
  • How does UX contribute strategically to the company’s success?
  • When was the last time you celebrated something as a team? Why?
  • What was your last big “failure” and how did the company react? What did you learn?
  • What is ____________’s why for existing?
  • What is special about the culture here that keeps you here?
  • What’s the last time you really saw your company culture shine?
  • How is the company culture different from other tech companies?
  • How does the company currently view the role of a “UX Designer”?
  • How does the company measure success?

NEEDS OF THE TEAM

  • What are the top 3 Vital skills that the designers on the team need help developing?
  • What does the team do well?
  • What is the next step of ____________’s UX Maturity?

ORG STRUCTURE / TEAM GROWTH

  • How many people will report to this position
  • What are their levels of experience?
  • What is the structure of cross-functional teams?
  • How do you see the design team growing?

PAIN POINTS / OPPORTUNITIES

  • If you could waive a magic wand and immediately solve 3 things what would they be?
  • This is your moment to shine. You are presenting to the whole company. You’re about to show the magic slide … the slide that rocks everyone’s world, secures your raise, and solidifies your value in the eyes of the executive team. What is that slide? What are the 3 talking points?
  • Imagine a dream day here. Everything goes right and works smoothly. You’re in a state of flow and have a big smile on your face. Walk me through that. What is the biggest leap of faith in that description?
  • What have you done to create an environment where innovation can thrive?
  • What is the biggest inhibitor to a culture of innovation at ________ right now?
  • What are the three biggest challenges facing your business over the next six months?

POSITION

  • What level of autonomy will this person have with their team?
  • What traits makes someone successful in this company / on this team?
  • What level of autonomy do teams have to design, build, and ship their work?
  • What does success look like for this position?
  • What are three things I’d learn in this role in the first year?
  • What would be my focus in the first 1, 3, and 6 months?

PROCESS

  • How is the design system currently being managed?
  • What kind of generative/evaluative research is being done currently?
  • How is collaboration with development currently happening?
  • How does UX fit into the Agile process currently?
  • How many projects do designers work on simultaneously?
  • What level of autonomy do teams have to design, build, and ship their work?
  • How are product decisions currently made?
  • Should you be moving faster and breaking things or moving slower and fixing things? Why?
  • How frequently is tech debt refactored?

PRODUCT

  • What are the three pieces of your product that are most valuable but also in the most need of an update?
  • For most jobs you can let a lot of stuff slide in the short term. But there is something that simply MUST happen. If you don’t deliver in that regard you’re screwed. What is that “one thing”?
  • What does your product do better than the competition? Why do customers choose you? Why do prospects choose the competition?
  • Tell me about a project you worked on in the last 6 months (who proposed it, how was it prioritized, what challenges came up, what would you have changed)

RESOURCES / CAREER GROWTH

  • What kind of budget exists for software, onsite research, & ongoing learning
  • How does the company help employees to improve their craft?
  • How often does the team “get out of the building”?
  • What opportunities are there for employees to learn new things?

SOFTWARE

  • Design?
  • Collaboration?
  • Backend?
  • Front end?
  • Cloud?

One more thing

There is one final question that I always like to ask at the end of every interview. If I only have time to ask one question, this is it. In the situations where I’ve forgotten or ran out of time to ask it, I’ve always regretted it. The question is this:

What concerns or questions do you have regarding my fit for this role that I can address before we end?

If that wording doesn’t sit right with you, here’s another way I’ve asked the same question in the past:

How do I stack up for this role against others you’ve interviewed recently?

I’ll admit, that the first time I asked this question, I was nervous. I had read the suggestion somewhere and decided to give it a try. It essentially is calling out the elephant in the room. It can be awkward, but that is precisely what creates the power and effectiveness. Just remember: you might feel awkward, but so do they. If you can make yourself ask it, their answer/reaction will

  • give you a wealth of information
  • make it clear how much (or little) they like you
  • gives you an opportunity to clear up any misconceptions or inaccurate assumptions the interviewer might have made about your fit or your experience.

More than once, this question has made the difference on my moving onto the next stage or not, and even more often this question has given me salary negotiating power I would not otherwise have had.

I typically get 1 of 4 reactions when I ask this question:

  1. They identify something that they’re concerned about that I DO have experience with but that hasn’t come out very clearly in the interviews. This is AWESOME because it lets me address the elephant in the room square on.
  2. They identify something that they’re concerned about that I DON’T have experience with. This is also good information. It lets me know the reason why they might not end up moving forward with me. (And lets me know what to work on if I really want a job like that in the future).
  3. Things get very awkward and they claim there really isn’t anything but I can totally tell from their reaction that there is. This IS actually good information, because it shows me that I’m probably not a fit for the role so I don’t have to wait weeks to find out. It also shows me that they’re not very transparent or candid (which at least for me usually means I wouldn’t have liked working there anyway).
  4. They quickly and without any awkwardness tell me that they were impressed and they don’t have any concerns at the moment. Often, when this is the case they’ll also give a couple examples of what they liked most about my background. This is the best kind of reaction and the one we all hopeful. This lets me know that they really like me, which can be very valuable information when negotiating an offer.

I hope these questions have been helpful. Searching for a job can be a daunting, discouraging process. More often than not, hiring teams are hesitant to provide any helpful feedback on their decisions which leaves most of us guessing on what we can improve or work on with our interviewing technique. Coming prepared with Insightful, Probing, Evaluative, Story-based, and Non-verbal questions can help and provide some clarity and show them the true value that you bring to the table.

As always, I’d love to keep the conversation going on Linkedin, Twitter, or the comments below. What questions you have found most useful in your interviews?

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Jeremy Bird

People-focused UX leader, designer, mentor, & problem-solver.