This is a work in progress post. My goal is to come up with 100 leadership questions.

Most of the question banks focus on entry and mid-career questions, by goal is to provide a resource that is specific to product leadership interviews.

In this article (which I will try to update regularly) I will list leadership-specific interview questions I see, as the headline suggests, I will get to 100.

This will not (typically) include what I consider the basics, found in numerous other posts on this website, for early and mid-career candidates. Those are table stakes for leadership candidates because the basics still apply.

I will provide prompts that overlap mid-career questions when I feel the wording is different enough to catch you off guard.

Below I list the prompts plus my thoughts on the prompt generally including why and possible insights interviewers are seeking.

General Behavioral

1. Teach me something you don’t think I know.

   • leaders need to teach others, this is a good way of seeing how you approach coaching and teaching, a major element of your job.

2. What are your superpowers? And their shadows?

   • A version of this gets asked at all levels, but the ‘shadows’ addition is poking more deeply than standard interviews might.

3. Fast forward three years, what is different about you then?

   1. Self-reflective and getting a sense of your ambitions. It will also give insights into how much you learn and change. If you ask someone with a growth mindset, they know they evolve constantly and should have an idea on what they are working on and patterns of their own development. Also, people who coach others might have more insights into their own growth areas.

4. When I go ask people you’ve worked with about you, what will I hear?

   1. You can get a version of this at other levels, but it is exponentially more common at the leadership level.

5. During your career, what has been your greatest achievement and why?

   • The IC version of this is ‘product you are proud of’ this wording begs something with greater impact.

6. Among the people you’ve worked with, who do you admire most and why?

   1. Looking for traits you admire and thus might try to use with your team. Less common at other levels, but still possible.

7. At this stage in your career, what have you learned about yourself? How are you different from other people?

   • Are you humble and self-reflective. Friendlier than the common tell me about a time you failed.

8. For the last few companies you've been at, take me through: (i) When you left, why did you leave? (ii) When you joined the next one, why did you choose it?

   • Leaders often move around more. They also often leave because of conflict and fit issues. More likely if you have short tentures. Be ready for it.

9. Who is the person whom you’ve had the most difficulty working with? Why was it difficult, and how did you work through it? What would they say about you today?

   • This is a variation on the disagreement with X partner we have seen earlier in our careers.