Over the last few weeks, I’ve been leading the recruitment efforts for a Senior Product Designer at my startup. I’ll skip this time the part of lecturing about how your CV and portfolio should look like (and how should not)…

For each candidate that seems relevant, I usually spend 30 minutes doing a screening call and another 45 minutes going through a portfolio review. During this time, I will learn and ask again and again about your process, design approach, and decisions you made on a given project.

And then, when it seems to come to an ending, I will ask:

“Do you have any questions for me?”

This is not a triviality, and definitely not out of politeness. No matter how much I ask and the answers I get — I usually learn more about a candidate, their maturity, and expectations from their questions to me than anything else. A candidate that doesn’t ask me anything, or asks shallow, expected questions is usually a turnoff. Please please please — challenge me!

The boring questions

There are some things that you definitely want to know, such as:

• Team and structure: How big is the team? Who will I be reporting to? Which tools do you work with? What will be my official title?
• All things money: How much does the position pay? Does the team receive budget for education/research/etc?
• Work environment: Are the developers in-house? Are they located in the same building/country? Who are the stakeholders I will work with on a day-to-day basis?
• All things users and data: Which options do you have for research and accessing users/data? Are there clear analytics, recordings or other data sources to review? Do you have defined KPIs?
• Support from leadership: To what extent do founders or management understand the importance and ROI of good UX? Should I expect to work hard to get a seat on the table?

While the answers to all these are important (and you should definitely have the answers before signing any contract), wasting the limited time we have asking these can be a major missed opportunity — and also makes you come across as “just another one”.

Usually, these questions are answered at any of the earlier or later stages, and if not, you probably will have the opportunity to ask them at the proposal stage, when we’ve spent enough time together to know you would be a good asset, and the whole organization is eager for you to join!

The smarter questions

To really stand out you need to catch me off guard. Make me think and sweat! Don’t forget you are looking for a place to work over the next 2–3 years or more, and you should be interviewing me at least as much as I am interviewing you. It is true that I have the final say as of you moving forward in this process. But smart interviewers won’t feel threatened by smart questions. If your interviewer seems disappointed after a smart or complex question, then maybe you don’t want to work with this person anyway.

There are dozens of good questions you can ask your interviewer when it comes to management, resources, opportunities, team, job position or process — but usually time is scarce, and you need to choose what can give you most benefit (as in any UX process, yes?).

To be specific, these are some of the things I wish candidates asked me as a interviewer:

What are the biggest challenges the team faces at the moment? What are the team strengths and weaknesses?

This question shouldn’t come as a surprise to an interviewer, but the answer could be really insightful for you as a candidate, because it may span a variety of answers. It’s easy for me to proudly list the team’s strengths and achievements, but it’s more difficult to be honest about weaknesses when I’m trying to impress a candidate.

It’s positive if you get from the interviewer an honest, humble answer and introspective about what challenges them personally. I‘ve never seen a company, big or small, that doesn’t struggle with anything. If you can’t get an honest answer, then it’s a red flag. And if you do, then you might have just uncovered an issue where you could bring value, hence, a great way to position yourself as a new hire.

If you could do magic— what current problem in the product would you solve right away?

Another question which should not be a big surprise, but valuable and insightful. This question is playful and leads the interviewer on giving you a focused product answer, which can also turn into some wonderful storytelling or venting on some hidden frustration — we all love to pinpoint what could and should be done better.

It gives you insight on the product and its challenges, on the interviewer’s perspective of what is more or less of a priority. Moreover, it is all about the product, which is something you will be working on intensely and hopefully interests you or excites you. This is important, because these will likely become your problems too if you join them.

Lastly, it opens up the conversation to opportunities that you might be able to take on, or help the team solve. If the answer is shallow or related to pixel-perfect issues… well, at least you will know what to expect.

What are the traits and skills that will make me successful in this position/company?

This question gives you an idea of what the company values most in its employees and helps you evaluate culture fit to some extent. It is an opportunity to do some self-assessment and see if, given the answer and the knowledge of yourself, you would be a good fit, and most importantly, the company is a place where you could shine. Else, if you really care and hope to work for this place, you could start preparing yourself with these values in mind.

You need the information to make a decision with eyes wide open. No company, manager, or employee is a perfect fit, but this is a way to understand this is a position where you will grow and bring out your best.

Also note if the company’s values surrounding work-life balance, communication or management style don’t align with your own. Make sure you don’t compromise over things that are no-no’s for you, otherwise burnout and frustration will be just around the corner.

Where is the company going in the next 5 years?

Things in a startup are very dynamic. Even in a big company, people move and priorities pivot over time. Basically, no one can really promise you a specific long-term outcome. However, as an interviewer, I could give you an insight on what are the possible developments, where would I like it to go, what could or could not be expected. Depending on the nature of the company, the answer will offer a better understanding of the company’s ultimate goals.

But mostly — it shows the interviewer that you don’t work in a bubble. As a designer you should focus on flows and screens as much as being concerned on how things develop on a company level, and the ways you and your team can bring value to the whole company. A designer who is not involved or aware of the business aspects will always be lacking some perspective, hence, not the best designer.

What are the expectations and achievements I should aim for over the first 90 days? What would make you think “I’m so happy we hired X!”?

This question helps me think of you as an existing employee AND a positive milestone. But also gives you some insight on how will your first days in the company be. Are they relaxed and willing to give you some time to adapt and learn, or is the volume of work so heavy that will become overwhelming? Consider if this image “painted” to you is something that excites you and makes you happy, or in the contrary, stresses you.

Do you have any doubts or concerns regarding my fit to this position that I can address before we end?

This is a scary one but trust me — if you have time for only one question, this is the one. It is a bit of calling out the big elephant in the room (or Zoom) and asking for feedback so far. It can be awkward, but it is powerful and effective. After all, you are giving me the opportunity to:

• state how much (or little) I like you so far
• clear up any concerns or inaccurate assumptions I may have about your fit or your experience

You should get one of these reactions from your interviewer:

1. The best scenario: They smile, quickly and happily say that they were impressed and they don’t have any doubts or concerns at the moment. Often, they will also remark what they liked about you most. This is super useful to know what are your power positions and qualities when negotiating with this company.
2. The interviewer has some concern about something you have experience with, that apparently hasn’t come out very clearly in the process. This is great! because it lets you address this issue right away. You may need to improvise yes, but this is better than nothing!
3. The interviewer has some concerns about something you don’t have experience with. Maybe not a happy situation, but this is still useful because it lets you know the reason why they might not end up moving forward with you, and what you can do to improve your odds in the future.
4. The sad scenario: Things get very awkward and the interviewer says something around “no, everything is clear” and claims there isn’t anything. But you can totally sense there is. This is also useful because it lets you know in advance that you are probably not a good fit for the role. And, it also shows that they’re not very candid or transparent, and they are probably not the kind of people you want to work with.