How to Interview Your Prospective Manager

I’m in the process of negotiating offers for my next role now. One of the things I’ve learned the hard way is how important good management is—especially for me, since I’m kind of a hard case, but in general.  It’s said that people leave managers, not companies, and I know that that’s been true of my experience. It turned out that I got very lucky in my early jobs, and up until recently my first managers were my high water mark.

Unfortunately the traditional job interview doesn’t give much time over to learn about the person who would be managing you.  (Sometimes you don’t even meet with them.) While you as the candidate are always implicitly interviewing your interviewers, it’s nice to have time set aside to it.

Mudge had not yet signed on as the new head of security when I got the offer from Stripe, but the recruiting team had told me he was considering it, and I knew I didn’t want to sign on to a new team without talking with the person I’d be reporting to.

I knew Mudge only by reputation and vaguely at that, and I didn’t want to join a team only to have some new manager come in and clean house and install all their own people. I delayed accepting until Mudge was ready to talk, and then we had a long phone conversation where I effectively interviewed him as my new manager.  (He was great, it turned out. 🙂

Going through the process again now, I’ve come back to these questions, and I’m going through the same process with my new potential managers.  It’s proving extremely fruitful.

Here’s what I’m asking:

  • What is your vision for the organization?
  • Where do you see the organization fitting in the overall picture at the company?
  • Where do you want the organization to grow?
  • What’s your plan for scaling the organization?
  • What do you like in a manager?
  • What do you dislike in a manager?
  • How do you view your relationship with the people who work for you?
  • What is your philosophy of management?
  • What makes you excited to come to work every day?
  • Can you tell me about a specific time that you were wrong, and how you handled it?
  • You have two employees who don’t get along. What’s your approach?
  • Have you handled harassment complaints before (sexual or otherwise)? What happened?
  • You have an employee who’s struggling. How do you handle that?
  • What do career paths forward look like for this position?
  • How much support is here to present at conferences/other professional development?
  • What are your preferences around hours/work from home?
  • How much contact do you need from the folks who work for you?
  • What problems do you see facing the company over the next three years
  • What problems do you see facing the industry over the next three years?

Interviewing your prospective manager is absolutely something you can and should do, and these are questions I’ve found useful.

Is there something I’ve missed that you like to ask about?  Leave a comment!