5 Questions to Ask a New Boss

The whole world, it seems, is changing jobs, with record numbers of people quitting every month. And every new employee has to face the same obstacle: a new boss.

Experts say your relationship with your new boss is critical, but that few people know how to start off on the right foot both professionally and personally. “All the great bosses I’ve had were up-front about their preferences,” says Michaela Buttler, a consultant at Korn Ferry’s career transition services. When you start working with a new manager, she says, be proactive: learn about their working style and expectations.

But what are the key questions to ask at the outset? And what answers can help you? Here’s what the experts say.

What are your goals and expectations?

While the hiring process may have given you a general idea of what’s expected, you should still check in with the higher-ups during the first week. “A lot of new hires get overwhelmed, thinking they need to know and do everything 100 percent within the first week, but most managers understand and expect some ramp-up time,” says Lemise Dajani, a career coach at Korn Ferry Advance. Make sure to be aligned with their onboarding timelines and goals, and prioritize your work accordingly, she says.

How do you prefer to communicate?

Don’t be afraid to ask about basic logistics, experts say. You should know how to reach your boss when there’s an emergency, or when something can wait a couple of days, or if you need to take a vacation, says Buttler. “For instance, with one manager I learned that if I need an immediate response, I should email or text them instead of using Teams,” she says. But some people don’t want to receive texts. Setting up these communication lines will save time and frustration on both ends, says Buttler.

What challenges are you facing?

Through learning about the problems your boss is facing, you’ll get a sense of how to proactively support them, says Dajani. You can create a good first impression and make their life easier.

Being aware of the issues they’re navigating will also help you act strategically when asking for something, and keep you from internalizing situations when your boss is unresponsive or short, she says.

What qualities do you love in the people you work with?

You can gain insight into your superior’s working style by finding out what qualities they appreciate in the people they oversee, says Buttler. Maybe they like employees who are inquisitive and share new ideas. Maybe they prefer those who stick to the manual. You can also flip the question and ask them about their pet peeves. For example, your boss could say that they don’t like people who bite off more than they can chew, then get overwhelmed, says Buttler. You’ll develop a sense of what to avoid.

How do you spend your free time?

Get to know your boss as a person outside of the job, but keep it professional, experts say. People like talking about themselves, so you can find topics that will allow you to bond and develop a deeper relationship, says Buttler. “We work better with people we know or care about, and it’s easier to do that when you know more about someone,” she says. If you don’t have much of a relationship with a person, you’re more likely to misunderstand them or take things out of context. 

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