Job Hunting? Ask These 4 Questions To Find the Best Boss

cheerful man in glasses shaking hands with recruiter on job interview.
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New year, new you, new job (evidently). According to a poll from, nearly all Americans (96%) are looking or plan to look for a job in 2023.

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Job seekers know to be on their best behavior and to avoid certain crucial mistakes when applying and during job interviews, be they over zoom or in person. However, what they may be less aware of is hiring managers and other executives working hard not to show any flaws. In other words, they’re trying to look like the perfect boss. So it takes asking the right questions to reveal whether they’ll be a good boss or not.

What questions should you ask during the interview process to find out whether your prospective boss, or bosses, are going to be unnecessarily difficult people to work for? The Wall Street Journal shared some tips:

1. “Which skills will my performance review take into consideration?”

This is a direct question that your prospective boss should easily be able to answer. What you’re looking for here is a direct answer. Run, don’t walk, if you get any of the following responses:

  • “We’ll know it when we see it.”
  • “A good culture fit.”
  • “My gut instinct.”
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These are vague and inarticulate responses. You can’t work with them at all!

2. “When do meetings start?” or “How quickly do you expect replies to your emails?”

These are also direct questions that require direct answers that are not difficult to give. Again, you’re looking for specifics here. If you get vague or narcissistic codes as replies, you know this is a bad boss situation.

3. “What does micromanaging look like to you?”

This is a question that may take your potential future boss time to answer, as it’s something that they may not have reflected on before. It’s important that both you and your prospective boss agree on what micromanaging is because a lot of bosses do this and don’t think they’re doing it. It’s in a similar vein as a person being passive aggressive and not realizing it (and may be another good question to ask: “What does passive aggressiveness look like to you?). Be on the same page about what toxic behaviors look like so that if either of you is found guilty of them, you can easily work them out rather than driving one another crazy with them.

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4. “Can we meet in person?”

In these post-pandemic days when so many jobs are remote and/or hybrid, it can be difficult to get in the same room together. But if you and the people interviewing can make it happen, do it. Just being around one another in person can help you both get a sense for one another that you would never get in a Zoom room.

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About the Author

Nicole Spector is a writer, editor, and author based in Los Angeles by way of Brooklyn. Her work has appeared in Vogue, the Atlantic, Vice, and The New Yorker. She's a frequent contributor to NBC News and Publishers Weekly. Her 2013 debut novel, "Fifty Shades of Dorian Gray" received laudatory blurbs from the likes of Fred Armisen and Ken Kalfus, and was published in the US, UK, France, and Russia — though nobody knows whatever happened with the Russian edition! She has an affinity for Twitter.
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