9 Questions to Get to Know Your Boss

You’ve joined a new team or a new manager is leading your team. How do you get to know them? How do you come to understand what they expect from you?

Questions min read
Engaged employee

The answer is the same as with getting to know anyone new in your life, whether socially or professionally—you start a conversation, you ask questions.

Of course, it’s not always easy to be the one starting a conversation, but establishing good rapport with your new boss will go a long way toward creating and maintaining a positive work environment. Talking with your boss is the best way to get valuable feedback on your performance, even when it is not annual review time. And, more times than not your relationship with your boss is one of the key factors in advancing your career.

With these things in mind, the following questions are a good place to start in building a great relationship with your boss, no matter who is new, or even if you just want to change things up in your relationship with your current boss.

Questions to Ask Your Boss


What is the preferred way to communicate with you? What if I need to get an important message to you?

Knowing a person’s preferred means of communication can avoid a lot of needless stress in a work relationship. Some people are great with email or texts and others prefer the opportunity to have the more spontaneous conversation over the phone or in person. It is important to pay attention to what someone says they prefer, but also to pay attention to how they really act: A person may say they prefer email but, in actuality, respond better when you pick up the phone or drop by their desk.


What is the company’s biggest challenge, and how can I help you tackle it?

Asking how you can help the company succeed shows initiative and that you are a team player. It also shows that you are not a person who waits to be told what to do, but asks what needs doing. It may not result in any new assignments for you, but asking, in and of itself, will be greatly appreciated.


When you think about the best team members you’ve managed, why do they stand out in your mind?

The answer to this question affords you insight into what traits the boss values in employees. It will also provide some behaviors to model yourself. Emulating the best of what a boss has seen in the past will help your contributions be noticed.


Is there any part of my job you feel you don’t know about, but would like to?

This gives your boss insight into your day-to-day that they might not have otherwise. It gives you a chance to be the expert and to teach your boss something. It could also open up a conversation about how a particular task can be best accomplished.


How will my performance be evaluated? What are the mileposts I should be keeping in mind?

This is an important question to ask of any new boss. It provides you with important information about what the boss is looking for in your work performance. It gives you a clear picture of where the company, and you personally, are headed, and gives you a sense of how to evaluate your progress toward specific goals.


If you had my job, what would you change about it? Why?

Whether you are new to the position or the boss is new to your team, this shows you are unafraid of change and willing to adapt. It is important to know why they would change something—it will help you and your boss craft new approaches to your position that may be more beneficial to the company.


What’s something I should start doing that I’m not doing currently? What should I stop doing? What’s something that I do well and should continue to do?

This is a something to ask down the road, once your boss has gotten a chance to get to know you and your work. The information you gather will be invaluable in that it will give you new tasks, help you to correct course, and allow you to receive praise and build on success. It’s a question that can, and should, be asked periodically.


How do you feel I fare versus my peers with regards to skill, engagement, and coachability? How do I measure up against the best team members you have managed?

Asking for this kind of feedback requires and demonstrates a high degree of emotional maturity and intelligence. It will provide you with a lot of valuable information about how the boss perceives you (and others) and what you can do to improve your standing in their estimation.


Do you have time for a follow-up conversation?

Any in-depth conversation you have with your boss regarding your performance should end with some variation on this question. It can be hard to process information in the moment, especially if feedback has been critical. It’s best to give yourself some time to digest what you’ve heard and respond at a later date.

A Conversation is a Two Way Street

It is important to anticipate that these questions will be the start of a conversation, not simply an interview with your new boss. Preparing yourself for the answers shows that you are not expecting the boss to do all the work of the professional relationship. Think about how you might answer these questions if you were her and, finally, be prepared to be flipsided occasionally—the boss’s answer to your question “What’s the company’s biggest challenge?” might be, “What do you think the company’s biggest challenge is?” Don’t get caught back on your heels. Your answer doesn’t have to be right, but it should demonstrate your own thoughtfulness.


Your relationship with your boss is an important one. Engaging them early and often will help you to build rapport and create an ongoing relationship with them that will reward you day-to-day and down the road as you progress in your career. Remember, it’s never too late to transform your relationship with your boss. Start a conversation—you never know where it will lead.

For additional questions please see 8 Brilliant Questions That Will Impress Your Boss, 12 Questions to Ask Your Boss, and 10 Questions to Ask Your New Boss.