10 Questions for Your New Boss

By Lorena Roberts on November 20, 2017

New job? New position? New boss? I bet you’re nervous. Don’t worry. You were chosen for the position for a reason. You obviously have a good head on your shoulders and you’re clearly qualified for the position.

However, there are some things you should make sure you ask before you get too far into the job. You don’t want to create bad habits that just make it tougher for you to receive a stellar performance review.

Here are some key questions for your new boss.

1. What can I do to make your quarter more successful?

This will show your new boss that you truly care about what’s best for the company. If you’re rooting for the team to have the best quarter yet, and you’re willing to do what it takes to get there, you want them to know that.

However, be careful about how much time you dedicate to your job. You could easily get sucked into working 50+ hours per week with no compensation. Make sure you think about what’s important to you and how far you’re willing to go to your new supervisor. Sure, you want them to be happy with you. But do you want to sacrifice your own happiness for it?

2. What is there to know about your management style?

Your new boss is either going to stay on your back, leave everything up to you, or be somewhere in between. Why force yourself to guess what their style is if you could just ask them? This will give you some insight into what they are expecting from you. Are they willing to let go of your hand to see what you can accomplish on your own? Or are they going to stand behind you during your lunch break to make sure you don’t go even one minute over? You’ll want to know that before you find out the hard way.

3. How would you like to receive my feedback?

A good company has strong internal communication. Everyone knows this. When you can easily talk to your boss about what is and is not going well, everyone feels more comfortable (and important) in general! If your boss doesn’t have a plan as to how to receive your feedback, it’s time to work on one. You want to be able to give suggestions, don’t you?

4. How can I help you with our biggest challenge?

They’ll probably be so relieved that someone is offering to help handle what they’re most scared of. Two heads are always better than one, and I can guarantee they appreciate the help. If they don’t need you, they won’t be afraid to tell you. But there’s more to gain from asking.

5. What are my most important milestones I should be making sure I’m hitting?

Telling your boss that you want to prioritize success for both yourself and the company as a whole will put you at the top of their list. They’ll be impressed that you’re planning ahead. If you want to perform well, it’s important to send that message.

6. Is there anything you’d like to know about me?

Disclosing personal details to your boss may feel uncomfortable. Don’t feel pressured to tell them every little piece of your life. But the foundation of building a relationship comes with knowing things about each other, no matter how general or how much they lack intimacy. You may find that you share more common interests than you originally thought!

7. How do you prefer to hear bad news?

Should you ever have to deliver bad news to your boss, you at least want them to receive it in a way they prefer. If they don’t want to hear it through the grapevine, it’s important for you to prioritize coming to them first. If they do want to hear it from their secretary, that’s just as important for you to take note of.

8. Would you like to have lunch?

Establish whether or not this is a boundary. Some bosses prefer not to be seen socializing with their employees, while others would prefer a more relaxed relationship. This is a good opportunity to get to know your new supervisor and start building that relationship that will (hopefully) serve you well throughout your career. If they don’t want to go to lunch with you, that’s not a personal attack. They aren’t personally rejecting you, just the idea of crossing that line into being more than boss-employee.

9. What are the pitfalls you’ve seen people fall into in this job/company?

If they’ve watched the last 10 people in your position prior absolutely fail at their task, you want their advice at least, don’t you? I would open the door to discussing what seems to be the most challenging part of the job versus what people tend to excel at.

10. Can we set up a meeting in a few days to make sure I understand all protocols fully?

You’ll want to put off the vibe that you’re wanting to do a good job here at your new job and you want to impress your new boss. It’s important that you sound committed to performing above and beyond “the average” employee. If you want to make a good impression with your new boss, ask to meet soon after your first day to be sure you’re doing everything you need to be doing.


Lorena graduated from The University of Tennessee in Knoxville last December with a BA in Honors Psychology. After some serious soul-searching, she's decided to pursue a Master's in teaching in order to teach middle school math! In her spare time, she enjoys spending time with her Whippet mix, Gio, at the dog park and binge watching Netflix with endless cups of Hot Cocoa.

Follow Uloop

Apply to Write for Uloop News

Join the Uloop News Team

Discuss This Article

Back to Top

Log In

Contact Us

Upload An Image

Please select an image to upload
Note: must be in .png, .gif or .jpg format
Provide URL where image can be downloaded
Note: must be in .png, .gif or .jpg format

By clicking this button,
you agree to the terms of use

By clicking "Create Alert" I agree to the Uloop Terms of Use.

Image not available.

Add a Photo

Please select a photo to upload
Note: must be in .png, .gif or .jpg format