5 Questions to Ask a New Boss

Nearly everyone gets a new boss when they change jobs, but last year millions of workers who didn’t make a switch still got a new manager. With firms cutting back heavily on middle management, the average number of direct reports per manager increased from under 11 in 2024 to more than 12 in 2025. This seemingly minor shift meant millions of workers were transitioned to larger teams under “consolidated” bosses. 

Odds are that the trend will continue this year, as organizations across industries thin out their management ranks. One in five businesses want to use AI to flatten their organizational structure,  which potentially means slashing over half of current middle-management positions, according to recent research.

Experts say your relationship with your new boss is critical, but that few people know how to get 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 Korn Ferry associate principal and executive career coach. 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?

What are your goals and expectations?

A new recruit can learn about their new boss from a recruiter. An existing employee can talk to other colleagues about the manager they’re inheriting. Still, there’s no better way to find out about the new boss’s goals and expectations than by directly asking. That way, you reduce the chances of any misunderstanding. “From there, focus your work on the organization’s goals,” says Sunny Levitt, a Korn Ferry principal and executive career coach.

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 to verify a deadline, 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 can save time and frustration on both ends.

What challenges are you facing?

By learning about the problems your boss is facing, you’ll get a sense of how to proactively support them. 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 you’re 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 seek out 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. 

Learn more about Korn Ferry’s Leadership and Professional Development capabilities.

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