My 3 Favorite Questions to Ask In An Interview

Sean L Adams
8 min readJun 20, 2021


Many firms are finding themselves in a unique position. After the initial devastating impacts of COVID on jobs, the market has opened some. But, of course, attempting to hire back employees has been challenging. So many firms are getting creative and thinking out of the box to bring in employees–which means more interviews than ever.

Hiring for any role has its unique challenges, and product team members are no exception; I would even say they are harder to hire. With limited time in front of each candidate, I must be succinct and glean as much critical information from them as possible. So, I am going to share my go-to interview questions. Keep in mind that my recruiting team and the product team do a great job digging in on a candidate’s technical and tactical know-how. They ask the questions to see if the person knows their stuff from an Agile SDLC perspective. So, my questions are designed to give me insight into how someone thinks, approaches problems, and setbacks and dig in on culture fit.

My three favorite interview questions:

  1. Tell me about the last time you failed and what you learned?
  2. Tell me what tasks you love central to the product role, what tasks you do not like, and why?
  3. How do you handle stress?

Tell me about the last time you failed and what you learned?

“Failure should be our teacher, not our undertaker.”-Denis Waitley

We can learn a lot about a person by hearing about their most recent failure. You need to hear this answer and decide if their latest failure is an area you are okay with them struggling in. For example, if they recently failed in communicating with the up chain critical information about an upcoming release, are you okay with communication potentially being an area of weakness for them. While they learned a valuable lesson, they could very well need continued growth and attention in communication and closing the loop.

You can see how they approach failure on a personal level. But, more importantly, how does the candidate manage what I call “the fall out of failure.” Then it would help if you listened for how they changed their approach to the area of the failure and possibly the product arena.

Lastly, you will want to see how succinctly the candidate can recount the failure to you–revealing a bit about their story-telling ability. I am a massive proponent of story-telling, and I frequently ask my team to improve this skill continuously. If the candidate can succinctly recount for me what happened, why it was a failure, the impact of said failure, lessons learned, and potentially how they do things differently today, I feel better about the answer altogether.

Think about it: What new questions do you ask yourself before deciding? What new processes have you put in place just because you do not want to repeat a past mistake?

If there is time, I ask about their most recent success as well. How the candidate handles and learns from success can be just as important. I want to hear from candidates what they learn from successes and what changes they have made from experiencing success.

Tell me what tasks you love central to the product role, what tasks you do not like, and why?

This is a crucially important question. A recent article cited the vast difference in pay associated with the vast difference in duties across product roles at different companies. Honestly, Product Management is done differently almost anywhere you go. So, when I am hiring someone, I want them to be happy with the way we work. That means doing challenging and fulfilling work. If the tasks of the product role they despise with all their being are the tasks I need the most focus on for success, I cannot with good conscience offer them the role even if they are a great fit.

Think about it: If I hire someone to do something they despise, I will be essentially asking them to “come on over and suffer; suffering is fun.”

How do you handle stress?

You see, for some people who hear this question, the first thing they think is, whoa? Is it stressful at Company A? If they ask, I do not think so, is my answer. It is true. I have been doing product management for over a decade. I have been leading product transformation through great teams for years, and while there are potentially stressful elements and challenges, I do not think it’s stressful. That said, I know many colleagues and associat4es who would think differently. The point is, I do not know what their stress threshold is, and I want to hear how they approach de-stress and stress management.

Everyone in the product arena has experienced or will experience our product being the persona non grata, and how we handle those times is going to be what makes or breaks us. So, with that question, I am certainly not waving a flag of, “Hey, there’s stress over here.” On the contrary, I think we have a very stress-free environment. I consistently ask my team to care for their mental health, take breaks throughout the day, and use their PTO. I think people do their best work when they are their best selves. Stressed out, angry, and upset are not people’s best selves.

Every hire should be a strategic hire.

I want to know about their method to de-stress, can the candidate be self-aware of stress triggers, etc.? Can the team tolerate their reactions to stress? For example, I once asked a candidate how they handle stress, and they answered that they need to organize the chaos and make sense of it all. That is not a wrong answer. Honestly, no answer is a wrong answer, but that answer was perfect. If that person is thrown into a chaotic project/effort, they will bring order because it is how they operate.

I asked this same question to another candidate, and their answer was they need to sign off and whiteboard out alone for a few hours. It was how they think. When asked what would happen if the answer, he came back with needed work. He said he would go back to the whiteboard for a couple more hours alone. I asked if/when he would include someone in that whiteboarding session, the candidate flat out said he would not; it is just how he operates. Again, no wrong/bad answers; I love brain dumping on a whiteboard to think through things too. But I cannot see how that method would create success in our organization because we are fast-paced and highly collaborative and have plenty of SMEs who can help us work through workflows and questions.

Last example of an answer that did not work for me: I asked a candidate how he handled stress. He said, “I just blow up on people.” He clarified that he literally would go full-on rage. We laughed; I found out he was partially serious. He worked in a start-up environment with ex-athletes, and they frequently yelled at each other. It was part of their culture and one of the reasons he was ready to make a change.

I get it, and I played football; we yelled at each other in love and grace and anger. Your volume is not always an indication of anger or frustration. That is something you pick up on in sports. I sincerely appreciated his honesty, but I could not in good conscience hire him. In this case, my team was fragile; we had been working on a particularly stressful product launch, and we were already burning candles at both ends, and we were barely keeping it together. I would not bring a stick of dynamite to the table.

A Case for the Candidate Project

Lastly, if you have a chance, you need to see how they work. So, ask for a Candidate Project. In this environment of hyper hiring, it might seem counterproductive to require a Candidate Project. Why would someone want to go through the trouble of a candidate project to hire on with you when they can go through a formal and less intensive interview process at Company B? As a hiring manager, you must change your way of thinking for this one. Understand, first, not everyone is suitable for the team. Second, if the candidate project is a requirement for hiring, then it becomes a table stake for you.

I give the candidate an epic: including two goals, the background, strategic fit, and four technical and business assumptions. Then I ask for the below:

  1. List out your additional assumptions (At least 3).
  2. Write user stories to achieve all the goals of the epic (At least 5).
  3. Create a mockup(s) of your enhancement(s) (At least 1).
  4. Create a simple project plan for a phased delivery/roll-out with a hypothetical timeline.

Think about it: Building a portfolio for product roles is challenging. We typically build products for companies and cannot share any technical details due to various agreements and privacy policies. Thus, while a candidate can prove they know nomenclature in an interview, a candidate project goes further and helps expertise, approach to work, and energy shines through 1,000x more than an interview can.

Hiring a candidate is not just about asking them questions. You will want to ask yourself some questions if you are hiring. Here are three questions to ask yourself when hiring.

What does success look like for this role in 30, 60, 90 days?
Layout a roadmap for learning, milestones, deliverables you are expecting. Now is also when you want to gather new hire resources to help your new team member get up to speed as soon as possible.

What problem are you trying to solve with the candidate that you could not solve without them?
Your answer should be about more than velocity; it is about persona, workflow management, and longer-term deliverables. Every hire should be a strategic hire.

What will your dream candidate be doing for the organization next year?
If every hire should be a strategic hire, how do we ensure that we have created a path to future growth? It is easy to go from one role to the next in 2 years in the technology sector. So, we should lay out the career path or promotion lane in our organization. Then, understand what you are looking for out of the next roles in that path. The answer to this question goes beyond you certainly. However, if you can not reasonably communicate the growth path for a new hire, you’re telling them to plan an exit.

However, as a manager, you must realize that simply because someone does a great job at role A and role B is the logical next step, they are not always well suited to the change for role B. Therefore, make sure your team can grow and be hired and promoted into competencies and not away from competencies.

There you have it, not only my three favorite questions to ask in an interview, but also the three questions we must ask ourselves as hiring managers.

What are your there favorite questions to ask in an interview?

Hi, I’m Sean; I’m passionate about CX and Products. Over the last decade, I’ve been privileged to lead product organizations at some of the most impactful companies in the world. Mainly in the healthcare space and most recently focused on an internal platform managing work for hundreds of clinicians and care for millions of patients. is my little corner of the internet; stop by anytime.