9 Smart Questions You Should Ask Your Boss to Help Get Ahead

Asking questions could signal to your boss that you’re interested in working hard and succeeding in your position.
Updated April 3, 2023
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It may be hard to make yourself stand out at the office or have your boss notice your work, but there are questions you can ask to get their attention.

You may be surprised that asking about new projects or signing up for courses could make a big impression on your boss. It may even help you make more money. If you can, talk to your boss on a regular basis so they know that you’re interested in constructive feedback on your work.

If you’ve been with your company awhile and want to move up, here are a few questions that you can ask your boss to help you get ahead.

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Are there any new projects I can be involved with?

insta_photos/Adobe manager talking to an office assistant

Your company may have new projects in the works that need some extra hands. Volunteering to jump on a new challenge is a good sign that you’re taking a proactive approach to your work. It may also get you some extra attention from your boss.

Some new initiatives may show off different skills you already have or let you acquire new ones. But whatever new work you take on, be sure it doesn’t cause you to get behind on the work you’re expected to do.

What resources or courses can I take?

Rido/Adobe businessman in meeting with his colleagues

Ask about potential resources or courses you can take to boost your skills for your particular position or to prepare yourself for a promotion. And remember to think outside the box with courses you may be able to find outside of typical company offerings. A local community college, for example, may offer courses in coding or other technical skills that may boost your skill set.

Within your company, talk to the human resources department to see what kind of tuition assistance you may be able to get for taking courses. You may be surprised to learn that your company can help you cover the costs of continuing education.

What can I do to reach my career goals?

Rido/Adobe business people discussing in modern office

A good manager will be aware of their employees’ goals and help them to achieve them. If you haven’t already, talk with your boss about your career goals and what the company’s expectations are for you.

Sit down with your boss to make a roadmap to see how you can achieve your goals within that company. By working together, you can develop achievable milestones that will help you grow in your career.

How is my performance?

Surapong/Adobe women are feeling stressed while working hard in their work

Sure, you may have an annual performance review, but don’t wait for that once-a-year meeting to get an idea of how you’re performing in the office.

Instead, consider setting up a meeting each quarter to touch base with your boss to see how things are going, what goals you’ve reached, and which ones you still need to work toward. You can also simply drop in from time to time to ask your boss how you’re doing and what more you can do.

Where can I go next?

88studio/Adobe people discussing on performance revenue in meeting

If your boss is a good mentor, they may be disappointed to see you move to a different team or apply for another position, but they also might be encouraging you to pursue new opportunities with the company.

Talk to your boss about any possible openings they may hear about in the organization and whether a new position could be a good fit for you to advance in your career. Don’t forget to ask them for a recommendation or to put in a good word if they think it could help you be seen by others in the company.

What are the secrets to your success?

Seventyfour/Adobe counselor with paper sitting on couch in front of patient

Your boss most likely didn’t get that position without working to achieve it. So talk to them about how they made their way through the company or how they got to that particular position. Ask them what skills helped them get there or how they were able to achieve their goals.

By asking your boss for examples of their successes, you can learn from what they’ve done with the hope of reaching a managerial position at some point.

What do I have to do to be in your spot?

WavebreakMediaMicro/Adobe business professionals at work

People may move from position to position, including your boss. Talking to them about what you might have to work on in order to take over if they get promoted is a good way to set yourself up for success.

It also can help to reassure your boss that if they decide to move on, they will be leaving you and your team in good hands as they move forward and hopefully set you up to succeed as well.

How can I help you?

Nina Lawrenson/peopleimages.com/Adobe computer and training business interns in night office with manager

You may need help along the way on a project or your general career path, and so does your boss. Check with them to see what you can do to make their work easier and get their goals accomplished.

It’s a good way to show you’re a team player, and your boss may appreciate your willingness to lend a hand and get things moving in the right direction for everyone.

Can you recommend some networking tips?

fizkes/Adobe businessman mentor giving instructions to trainee at workplace

Networking is a great way to get your name out there in the field, and a good option to advertise your company as well.

Talk to your boss about online options like LinkedIn where you can connect with people they may know or ask them to post a testimonial about your work. You also might want to see if they have recommendations for in-person or virtual networking events that can boost your profile with other people in your field.

Bottom line

Oleksandr/Adobe pleased young female boss with documents looking ahead

It’s a good idea to start asking questions now so you can set yourself up for success later. You don’t have to ask your boss all of these questions, but choose a few questions that fit your particular situation or where you are at this moment in your career.

It can also get you in the habit of keeping good lines of communication open between you and your boss so you both can find success moving forward. And it’s a great money move if you want to make a good salary as you progress in your career.

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Author Details

Jenny Cohen Jenny Cohen is a freelance writer who has covered a bit of everything, from finance to sports to her favorite TV shows. Her work has been featured in The Wall Street Journal, USA Today, and FoxSports.com.

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