Interviewing Your Next Boss

A couple of times in my career, I've ended up with jobs that sounded good on paper but left me wondering, "What was I thinking?" The management responsibilities and technical challenges were where I wanted to be, but my manager's style was all wrong, at least for me.

Good hiring managers don't just look for skills. They look for a good fit between the candidate's workstyle preferences and the culture of the group, and so should you. Don't just think about the on-paper aspects of the job; consider how you prefer to be managed. Analyze what you want in an employee in this position, the manager of you.

Think about past managers you've worked well with. What made those relationships work? How about bosses you didn't click with? What were some of the factors that made those relationships difficult? Identify the factors that will knock a potential boss out of the running for you.

Look at your own personal preference and style:

  • Is it important to you to be able to talk to your boss about risks and problems as well as what's going well?
  • Is it important to you to know what is expected so that you can work within those boundaries?
  • Do you prefer to work with broad discretion to carry out your responsibilities in your own way?

Use behavioral interviewing and open-ended questions such as these:

  • What sort of information is important for you to have in status reports or one-on-ones?
  • How have you approached a situation where a direct report comes to you with a serious project issue?
  • How do you prefer to learn about problems or obstacles?
  • How have you defined the boundaries of this position in the past?
  • Tell me about the results you look for in this position. What is most important in the way the work is done?

Be prepared for the candidate boss to be a little unsettled by this sort of questioning. After all, you're turning the tables, and he may feel on the spot. Watch how the candidate boss responds: Does he pause and then answer your questions? That's a clue that your manager candidate is open to exploring your working relationship. Does he become angry and snap, "I'm asking the questions here"? Cross this one off your list.

Finding a new job isn't just about the title, job description and technical skills. It's about relationship and fit. Identify what you want in a manager. Ask questions. Look for clues. It's all information that will help you choose an employment situation that will work for you and your new employer.

Esther Derby provides high-leverage facilitation to start projects on a solid footing, assess the current state of projects and capture lessons learned. You can reach her at or by visiting

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