8 Questions to Ask Your Boss to Enhance Your Career Growth

In your lifetime, you’ll probably have several bosses. Some bosses will be friendly, while others you won’t hear from until performance reviews.

Flying under the radar when it comes to your professional life is not a good strategy. Your relationship with your manager can be impacted by your ability to get honest feedback from your supervisor.

Here are some questions that an expert will ask to help you (and your supervisor) get started on the right path.

1. What was your weekend like?

When you should ask: Jodi Glickman is the author of the book “Great on the Job: What to Say, How to Say It: Secrets to Getting Ahead.”. It’s a great way to build a relationship with your boss and to connect on a level other than work.

Should you ask? By asking, you will learn about her priorities.

2. What is your biggest concern, and how can I solve it for you?

When do you ask? This is an excellent question if you are new to the team or job. It will help you understand the job’s demands. Ask when a new manager joins your team. You’ll learn about his priorities. You can use this question at any time, for example, when your boss is busy and you’d like her to know that you are available to help. This will boost your “valuable employee” rating.

Why is it important to ask? “It shows you are strategic, thoughtful, and take initiative. You’re not waiting to be told what you should do,” Glickman says.

3. What makes your best employees stand out from the rest?

When to Ask This is not the kind of question you would ask in a casual setting. You should only ask this question during a performance evaluation or after your boss has given you some tough feedback.

Why do you ask? “If you have a good working relationship with your manager but are looking to improve your performance, get a promotion, or raise, then this is an excellent way to find out what she values the most,” says Glickman.

4. I’m excited to work on ______ with you. You’ve been working on a project with me. Can I ask for your feedback?

When you should ask: Whenever you begin a project, join a team, or take on a lengthy assignment, tell your manager that you would like feedback.

Why is it important to ask? “The best and most effective way to obtain real and meaningful feedback is to plant seeds in advance by asking your boss to provide feedback before you are actually in need,” Glickman says.

5. I want to do well on this assignment. Are there any templates you could refer to, or is there anyone in the team who has done well on a recent assignment?

When should you ask? At the beginning of a new project.

Why you should ask Most likely, your boss already has an idea of what she wants a project to look like. Glickman advises that by asking for help up front, you can save yourself and your boss from frustration and wasted time.

6. I would love to supervise _________. Please keep this in mind when assigning projects.

When should you ask? When you are excelling at your current job and ready to take on a new role, know that your workload will not be affected.

Why is it important to ask? According to Glickman, “Managers are attracted to employees who want to grow and learn. They also love to take on new challenges.”

7. What should I do? What should I do? What should I keep doing?

When should you ask? Ideally, your boss would answer these questions during your performance evaluation, but if they don’t, then it is up to you to ask. You can request a one-on-one meeting if you feel you were not given the information you needed during your review.

Why is it important to ask? “There’s probably some things that you do that your boss likes and others that he would rather you stop doing. But he’s never had the guts or heart to tell you,” Glickman explains. This line of questioning will make it easier for him to tell you.

You can gently bring up the subject if your boss tells you that you are doing a good job and don’t have to make any changes. You can ask a question such as, “I’m glad to hear that everything is going smoothly, but I would like to challenge myself and move up in the world.” What else can I do to ensure I’m promoted next year?

8. As I process all of this information, I am sure I will have some questions and thoughts. We could schedule a second conversation within a few days.

When should you ask? At the end of a less-than-stellar performance review or after any conversation in which your boss provides valuable feedback,.

Why is it important to ask? It’s difficult to ask questions and think quickly when you feel beaten up. You’ll be able to take a few days off to gather your thoughts and come up with new ideas. Glickman says, “The last thing that you want to happen is to lose your cool.” Remember, the purpose of feedback isn’t to make you happy. You’ll be able to do your job better.

ALSO READ: 6 Steps to Build a Strong Relationship with Mentor


In conclusion, a good relationship with your boss will help you grow in your career. Begin by establishing a personal connection, asking about the boss’s priorities and offering assistance. Ask for feedback and understand the qualities of top performers. Also, express your interest in leadership positions. Ask for advice on projects, and set up follow-up conversations after evaluations to reflect. This open communication will foster a positive relationship at work and help you to advance your career.

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