My 3 Go-To Interview Questions

In  my life before technology, I was a journalist and I asked questions all the time. The quality of questions drove the quality of my stories so I was always striving to have the best interviews possible. The conversation I dreaded with an editor was one where they asked why a story didn’t include a seemingly obvious perspective or piece of information. The usual answer was “I didn’t ask.”

So early in my tech career when I was scheduled for my first interview with a potential co-worker, I confidently walked into the room thinking “This will be easy. I got this.” Imagine my surprise, and embarrassment, when I realized I had no idea how to interview this person. I flailed around asking questions as they came to me for a very long 30 minutes. 

I left that room knowing very little about why that candidate was or wasn’t good for the role, and a determination never to be in that position again.

The key lesson I learned was that as a journalist I excelled at asking questions not because I was naturally gifted at it, but because I always prepared before I showed up. I knew what information I needed, the best way to ask about it, and what I would do if I didn’t immediately get the information I needed. 

SInce that first interview, I’ve interviewed hundreds of potential co-workers - program, project and product managers, engineers, designers, marketers, individual contributors, executives, future bosses, peers and employees. In that time I’ve honed my interview questions down to a science to be sure I leave the room confident I understand how someone would be to work with. 

After almost 20 years of interviews, I have 3 questions I always use, regardless of the role. 

Tell me about your greatest accomplishment.

I love this question because it tells me so much about what gets a candidate excited, what they are most proud of, how they contributed and why it matters. It immediately tells me a lot about the scale of the challenge they’ve worked on, and how they position their contributions against their co-workers. It often provides great opportunities for follow up questions and conversation that tells me a lot about how they would respond to me in a meeting.

I’ve heard answers both professional and personal: Shipping a big software release, shutting down a project, beating cancer, climbing a mountain. 

I often learn so much about a candidate in the 3-5 minute discussion that follows this question, that it drives how we use the other 15-20 minutes of our time together. It’s  insightful enough that I sometimes use it at dinner parties or networking events.

Tell me about a time you made a mistake and what you learned from it.

I love this question because it requires candidates to talk about something that makes them a little uncomfortable.  

Answers to this question tell me how someone might deliver bad news and respond to being challenged. It shows me a concrete example of their decision making process. It also shows me how self-aware they are, and how important they feel that learning and changing is to their success. 

A good number of people give a non-answer to this question at first (“I cared too much”) and I follow up a couple of times, respectfully but pointedly, to get to the root of that (“I let my passion get the better of me and I lashed out at my co-workers”). This interaction gives the candidate a sense of what they can expect from me when we have to work through something together. 

I’ve had a handful of people tell me they haven’t made mistakes, and that is always a red flag. Everyone makes mistakes - it’s what you do after the fact that counts the most. 

You are responsible for taking on <something new they know nothing about>. What do you do first?

This question comes in a few forms, depending on the role. For project or program managers, I usually ask how they handle localization, assuming they’ve never done it before. I’ve also asked about testing elevators (QA) and UX for a new interface (Design).

I ask this to get a sense of a candidate’s approach to solving something they have never done before. Do they ask follow up questions? If so, which ones? Do they jump right to solutions? What do they focus on first? How do they respond to being asked to problem solve in real time?

It’s great insight into someone’s experience level, their approach to asking questions, comfort with doing so, and how well they can articulate their thinking. It’s also another question that gives candidates insight into what it’s going to be like when they work with me. 

The best answers to this questions have been ones where we have a true conversation about the project and collaborate on getting to a result. 

Summary

These three questions don’t have right or wrong answers. They provide a lot of information quickly and provide a great jumping off point for more specific questions. They  also give me and the candidate the best chance of learning how it might be when we’re in a room together solving business problems. 

Do you have go to questions you always use in an interview? I would love to hear them!