Hire Better Managers: 35 Interview Questions for Assessing a Candidate

We asked top hiring managers and startup leaders to share their favorite questions for interviewing management candidates.

Outline

1. QUESTIONS FOR ASSESSING LEADERSHIP STYLE

   1. 1. What are 1-2 questions you always ask your team members in one-on-one meetings, and why?
   2. 2. If I asked someone on your team about your leadership style, what would they say?
   3. 3. Tell me about a time when you delved into significant detail and got your hands dirty.
   4. 4. What ritual or practice have you found to be most effective for helping your team connect and collaborate?
   5. 5. Why did you leave IC work?
   6. 6. How do you balance being a manager and a coach?
   7. 7. What do your direct reports like about you? What does leadership like about you?
   8. 8. Walk me through the most significant change you’ve made as a manager in response to feedback you’ve received about your leadership.
   9. 9. When two team members disagree, how do you help solve the disagreement?
   10. 10. What’s something new you’ve learned recently?

2. QUESTIONS ABOUT HOW MANAGERIAL CANDIDATES SET GOALS AND COMMUNICATE STRATEGY

   1. 11. What processes have you put in place to ensure that each person on your team has a clear idea of the team's goals and each individual's role and responsibilities?
   2. 12. Can you share the vision for your org at your last company?
   3. 13. What dashboard do you open up every morning?
   4. 14. Let's say you have to make a challenging announcement, like sharing news of a re-org or even a layoff. How would you prepare? What would you say to your team on the day of?
   5. 15. Describe a time when you felt your team wasn’t shipping frequently enough. What did you do about it?
   6. 16. Tell me about a time when you made a meaningful impact on revenue / market cap / cost savings.
   7. 17. Tell me about a time when you had to make a strategically important decision with limited data.

3. QUESTIONS ABOUT MANAGING HIGH AND LOW PERFORMERS

   1. 18. Who is the worst performing person on your team and how are you working to make them better?
   2. 19. How do you evaluate performance on your team?
   3. 20. Can you tell me about the last time you helped a star on your team find their dream job?
   4. 21. When new positions have opened up on your team, did you promote from within or hire externally? What is your philosophy on this?
   5. 22. Tell me about someone you manage who’s been really successful at your company, and what made them so successful.
   6. 23. Can you tell me about one of your direct reports’ accomplishments that you’re most proud of?

4. QUESTIONS FOR TESTING THE CANDIDATE’S CHOPS AS A HIRING MANAGER

   1. 24. Who on your team would you be happy to work for?
   2. 25. Tell me about a time when you had to hire for a challenging role.
   3. 26. What are the qualities that you look for when you’re hiring and do you exude them yourself?
   4. 27. Walk me through your end-to-end hiring process.
   5. 28. How do you help new team members ramp-to-impact quickly?
   6. 29. How do you keep track of the careers of the folks you’ve worked with previously?

5. QUESTIONS FOR EVALUATING HOW THEY WORK WITH OTHER TEAMS

   1. 30. Can you tell me about a time when you helped guide your team into better alignment with another team?
   2. 31. Which organizations have typically been your most important partners?
   3. 32. Which organizations have you encountered the most friction with?
   4. 33. Tell me about a time when you influenced another team in the company that had a diametrically opposed point of view.
   5. 34. When you’ve worked as part of a successful team, explain the secret sauce that helped those activities go well.
   6. 35. Describe a shitty system at your last company. What did you do about it?

When your startup is just a few folks who can all fit around the lunch table, management chops may not be top of mind. At this stage, when it’s just the founders and a few early employees, the management structure is probably pretty flat, and folks are instead left to ship quickly and largely manage themselves.

But as the product and customer base grows, so too does your org. You start hiring en masse, and suddenly that "move fast and break things" mentality needs heaps more guidance to ensure it’s moving in the right direction. At this stage, developing a stable of highly skilled managers at the company becomes priority number one.

But spotting folks who can become high-impact leaders at your company is exceptionally challenging in an interview setting. While you can probe IC skills with a coding test or other function-specific take-home projects, unraveling all the nuances that go into managing people can be incredibly tricky — especially with just a narrow sliver of time with each candidate.

So when sitting down with management candidates, interviewers tend to resort to the same ho-hum questions that barely scratch the surface. Think, “How do you describe your management style?” or “How do you motivate your team?” Any candidate who’s put the bare minimum prep work in before interviewing will have a perfectly prepped answer at the ready for these basic questions.

You’re not looking for a mediocre manager to lead a team — you’re looking for someone exceptional. So ditch the rudimentary questions and dig deeper.

Given the high-stakes nature of every hire, we’ve found that interview chops are always in need of sharpening. We’ve published a few of these interview guides on the Review in the past (like these 40 favorite interview questions and another 40 questions specifically for candidates to ask the hiring manager) — and they’re always fan favorites.

So we put out a call to some of the sharpest folks in our network for their best interview questions for management positions and assembled their responses into a new can’t-miss guide for hiring managers. We’ve broken the list down into a few targeted categories, segmented by some of the most critical management traits. We hope at least a few of them make their way onto your own list of favorites.

Looking to quickly access all the interview questions in this guide (plus some extra bonus questions)? We’ve assembled 50 questions into a handy guide for your next interview with a managerial candidate. Download the PDF below.

50 Interview Questions for Manager Candidates

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