The 7 Most Useful Interview Questions

Distilled from hundreds of interviews over the last 15 years. There’s something specific I hope to learn from each question. The first one is an important level-setter…

1) What have you learned today (or since we last spoke)? About the role, the team, the company, the market, etc.

If they haven’t learned anything new, either they’ve done little research since the phone screen, and/or the other interviewers didn’t let them ask many questions. In either case, I need to know that.

2) Describe the best thing and worst thing about each of your last two jobs. Explain, provide backstory, etc.

These answers are so telling of character, and help create a sense of their professional narrative and how they got here. Chronic complainers are revealed here, as are those who play politics or blame games. Ambitious folks often remark about opportunities to grow or learn, or the absence thereof. No demerits given for falling out of love with the work or the industry, or a re-defined role or org change, but the explanations are useful context.

3) What would you point to, personally, professionally, or academically, that best represents your work ethic? Give me the full story.

Looking for evidence of grit and sustained passion for a challenge. A weak answer is quickly self-evident and I move on; they’ll have to say something incredible thereafter to save themselves from getting declined. The best answers often come after a pause for thought, as they consider several situations where they have invested large amounts of sustained effort. If a meaty answer is given, I’ll dig and watch them relive the journey and teach me what they came to learn along the way — giving me confidence in their can-do attitude and willingness to commit to hard work. Bonus points for team endeavors.

4) What would you point to, personally, professionally, or academically, that best represents your biggest screw-up? Give me the full story.

I’m looking for a growth mindset (thanks, Carol Dweck). How big is their ego? Can they admit their mistakes and talk about their failures candidly? What did they learn from it? How have they put the resulting insights into action? If they provide a “minor” failure, I’ll ask for something “bigger”. If they genuinely have nothing, I wonder if they possess a fixed mindset or shy from challenges.

5) If I got each of your last 3 managers into this room, without you present, and asked them to agree on the one thing that you need to improve, what would they agree on? Why?

More drilling for the growth mindset. I want people who want to do the best work they’re capable of, and it’s easier to improve if you collect and process feedback well. Do they agree with their managers’ assessment? Were they eager to hear the feedback and willing to act on it? How have they addressed these areas? I note these answers and try to correlate in reference calls.

6) What would you like to be doing 5 years from now? Realistically. Why?

Turnover has cultural and management overhead costs, so I want to get familiar with their ambitions. I usually don’t want someone in a role unless it fits their professional trajectory or they openly admit they’re experimenting to determine their interest and aptitude for such a role, in which case their character, grit, mindset, and habit of doing their best work may still carry the day. Bonus points for strivers who acknowledge the path and hard work entailed in getting there. Negative points for persistent aimlessness or resentment about where they should be.

7) What questions do you have for me?

Perhaps the most revealing question. How thoughtful have they been about apprising the fit with their skill and goals? About the industry we’re in? About the opportunity we’re pursuing and the problems we’re trying to solve? If they are sharp and thoughtful, these traits will be manifested in their questions.

Over the years, I’ve hired ~100–150 people and interviewed several hundred more (at Bloc and elsewhere prior), but I’m always eager to further hone my interviewing skills. So thanks in advance to those who drop links in the comments to other helpful interview questions and practices they’ve seen!