Ask these five questions to find out if you’ll like your future boss

You don’t want to accept the wrong job–and bosses don’t want to hire people who won’t stick around. Here’s what to ask to find the right match.


When you’re interviewing for a new job, you may not always feel like you’re in a position to be particular. Maybe you’ve been laid off, or you don’t like your current job and are desperate for a new gig. Perhaps the new job seems like just the opportunity you’ve been waiting for.

But here’s something you shouldn’t overlook: Will you like working with your new boss? People leave managers, not companies, the adage goes–and that’s especially relevant now, as companies jockey for the best talent. “I would rather take an imperfect job for an awesome boss–because an awesome boss is going to accelerate me–rather than the perfect job for a boss that’s not going to take any interest in me,” says Emily Bermes, an executive coach who runs her own consulting firm. “Go after the better boss every single time because it will completely change the trajectory of your career.”

If you’re trying to suss out how you might like working for a prospective boss, these are some of the questions you should be asking.


You could also phrase this as, “Talk to me about the employees that you most love leading,” or “What type of team do you like to run?” These questions can do double duty–a thoughtful answer tells you they have prepared for the question. Lauren McGoodwin, the founder of Career Contessa, recommends thinking about which qualities you have and have not liked in other bosses before an interview. If you prefer to work more autonomously and a potential boss prefers a more collaborative team–or sounds like a micromanager–chances are that your working styles may not gel.

Posing a question about the employees they enjoy working with can help you figure out which qualities they prize most, Bermes says. The opposite question–“When you don’t work well with someone, what are some of the reasons for it?”—can also be illuminating. “You start to get a sense of both what you’re shooting for and what you’re striving to avoid,” Bermes says. It’s also important to ask other people in the interview process–recruiters or other people who report to the boss in question–about how they work with the rest of the team. If necessary, you can ask a recruiter to connect you with people who can speak to this. “Leaders certainly have reputations,” Bermes says.


“In my experience, particularly at the executive level, the fail rate is 40%-50%,” says Bermes. “Often it’s because the onboarding is handled so badly that people don’t have a fighting chance.” Ask a potential boss what good onboarding looks like, she says, to best understand how much support you will get, and what the learning curve will be–and whether it’s enough for you to succeed in the position. When it comes to leadership roles, Bermes says, some companies might expect you to come in fully prepared for the position, while others will allow you a couple of months to get your bearings.

“Organizations don’t want to make the wrong hire, and individuals don’t want to take the wrong role, she says. “I feel like in this day and age, it’s much more about due diligence both ways, because the organization knows that if the candidate can’t figure out if it’s a good fit, they may not stay–and then they’ve wasted the recruiting costs and the business time.”


This is particularly important if you prefer to get regular feedback. McGoodwin recommends asking if it’s part of the culture to give and receive feedback frequently, or something you would have to initiate.

You should also watch for implicit indicators of how they give feedback, she notes. You can gauge how an employer might treat you based on how they navigate the interview process–whether they are responsive to emails or prepared for your interview, for example.


When you ask about hours, McGoodwin suggests also asking about how they communicate and which tools they use. This can tell you which medium they prefer–email versus Slack, for example–and how responsive they expect you to be, especially after hours.

McGoodwin adds that it’s worth looking out for whether a potential employer asks questions about your life beyond work (within reason, of course). “We live in a culture now where you can literally work 24/7,” she says. “Does your boss have any respect for–or even acknowledge–the fact that you have a life outside of work?”


For women and minorities in particular, it’s important to ask about diversity and inclusion policies to get a sense of how you might be supported both by your boss and the organization as a whole. McGoodwin says you can ask outright about the number of women in leadership positions, for example, or how company initiatives help promote more women into those roles. It’s important to raise this with other people you speak to as well, to see “how those values are lived in every day,” she says, and whether men are being included in the conversation. Asking questions like, “Give me an example of a time when your company showed their commitment to inclusion” can show you how committed a boss is to reinforcing those efforts in their own leadership.

But even when people say all the right things—sometimes especially when they do—trust your gut. “I certainly think you can get a vibe from someone,” Bermes says. “People can say all the right things in all the right ways, and intuitively you just may not trust them, or you might feel creeped out by them.” If someone rubs you the wrong way during an interview, there’s probably a reason for it. “If people make you uncomfortable when they’re on their absolute best behavior, I would be leery,” she says. “The older I get, the more I’ve learned not to ignore that stuff.”