Ten Questions for Your Next Boss

Liz Ryan

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It’s a very funny thing, a job interview - especially if you make it past HR, and you’re face-to-face with your next prospective manager. There is no one more important in your job satisfaction equation than your boss. So here you sit, and he or she is asking you questions, and you’re trying to get a read - what will this person be like to work for? Is he patient? Is he smiling? Is he testy? Are there any questions that you can ask him, to get a sense of his management style? Here are ten, to get you started. I doubt that you’ll get the chance to ask all ten of them, so pick your favorites in advance!

1) Can you tell me about some of your proudest professional moments so far?

2) What are some things that have driven you crazy about subordinates in the past?

3) What is the skill or attribute that you most value in a member of your team?

4) What sorts of things do you do outside of work? (Listen to me now: if you don’t feel comfortable asking this question, that’s a big red flag. It’s a perfectly appropriate question to ask the person who might be managing you, a few weeks from now. If she’s giving off a vibe that such a question would be too intrusive, THAT’S NOT GOOD. )

5) Can you tell me a little bit about the interactions that happen within the team?

6) I’d love to hear about my predecessor - what worked in the job when he or she had it, any elements that you’re changing now that the job is open again, and what happened to that person. (See the note after question #4 - ditto for this one. )

7) What keeps you up at night, work-wise? What’s your biggest concern?

8) I don’t know whether you’ve ever done the Myers-Briggs assessment or DiSC or any of those, but how would you describe your communication style - more forceful, or more interpersonal, or detail-oriented, or what?

9) Can you tell me about your boss, and his or her big priorities?

10) From our conversation so far, what are concerns that you may have about me? Where do you think a person like me might thrive in this job, and where might someone like me have trouble?

You NEED to feel comfortable with your next boss. I just heard from a friend in Chicago who had to leave a job after six months because the fit between her and her boss was atrocious. Loving the work, the rest of the team, and the view from your office window is not enough when you work for someone you don't like or don't trust. Don’t take a job like that. LIKE your boss.

I know, it’s not always easy. When you're under pressure to find a job, it's easy to overlook little quirks (and even big ones) that could make a person tough to work for.

But you’ll know right away, if the interview doesn’t create a safe space for you to ask questions like this, that working for this boss might be dicey. And then you can decide whether you want the job so badly that you’re willing to walk eyes-open into a possible bad-boss situation to get it.

Liz Ryan is a former Fortune 500 HR executive, a workplace expert and the founder of the online community WorldWIT. Liz is an international speaker on at-work issues, networking, and work-life topics. She lives in Boulder, Colorado.


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