40 Smart questions to ask your boss

Marlo Oster
July 19, 2022
3
Minutes

Asking your boss a question can be an intimidating prospect, but never asking any questions at all is a bad look that can make you seem disengaged and uninterested in your job. But what questions should you ask, and how do you go about doing so? In this post, we’ll share 40 questions to ask your boss during one on ones, performance reviews, and casual conversation.

We’ll also break down why it’s important to ask your boss questions, where to ask your boss questions, and when the most opportune moments are. 

Smart questions to ask your boss: the why, where, and when

Why should you ask your boss questions?

The relationship you have with your boss is one of the most important relationships to maintain in your career. It’s your boss who judges your performance, recommends you for promotions, and decides what work you’ll be in charge of. It is critical that you maintain and continue to build rapport with your boss. You want them to see you as someone who is passionate and interested in your work. 

Questions are the backbone of great relationships. You wouldn’t go on a first date or continue to develop a friendship with someone without asking questions. It’s how you get to know another person, and it’s how they know you are interested in building a relationship. In this way, your work relationships are no different (although the questions are definitely different!)

It’s not only about building strong workplace relationships. Asking smart and engaging questions shows that you are a curious person who is interested in other people. Asking your boss questions at key opportune moments will give them the impression you are interested in what they have to say, are passionate about your work, and are interested in continuous improvement. 

It’s really a win-win for everyone. To your boss, you look like a more interesting employee who is deeply engaged in their work, and at the same time, you gain insight into how your boss thinks, what their interests are, and where the company is headed. You acquire knowledge that will help you prioritize, problem solve, and make better decisions, which will play a crucial part in your professional development and ability to manage up

Where should you ask your boss questions?

There’s no one and only place to ask your boss questions, but there are spaces that are better than others. Your weekly one on ones, for example, are an ideal time to ask your boss questions—that’s really what they’re set up for. 

If you work at an organization where consistent one on ones occur, this is an ideal time to ask questions relating to your work, questions about the company, and casual questions to get to know your boss. 

💡 In WorkPatterns, you can keep a list of the questions you want to ask during your one on ones in the private notes tab of your workspace.

If your business doesn’t run regular one on ones, you may have to book a dedicated time with your boss to go over some of the questions you’ve saved up. If it’s something they might need to think about or gather information on, add it as a discussion topic for the meeting so that they see your questions in advance. 

In addition to one on one meetings, you can ask your boss questions during a feedback cycle or 360 review

Lastly, it’s good to have a few more casual rapport building questions built up that you can ask your boss should you cross paths in the break room, elevator, or before a meeting. 

When should you ask your boss questions?

The timing of questions for your boss is critical. They are very busy people, and interrupting them at a less than ideal moment can create an awkward situation or illustrate to your boss that you don’t value their time. 

Ensure you are continually asking engaging questions, but don’t overdo it. That also means you should make your questions count. Your boss only has so much time to dedicate specifically to you, so make your questions worthwhile. 

Don’t let your questions become a distraction. There should be a clear reason behind your questions, even if that reason is to build rapport and get to know your boss better. 

If you have legitimate concerns about your position, performance, or the workplace, ensure you set up dedicated time to speak to your boss. If there’s something that’s bothering you or of deep concern, reach out before the situation becomes worse. A good boss will make time to answer your questions, and they will want to hear your concerns as they work to improve the workplace for you and your colleagues. 

15 Questions to ask your boss in a one on one

One on ones are an ideal time to ask your boss questions because that’s what they are designed for. The one on one is an opportunity for you and your boss to get to know one another better and for you both to interact and answer questions that might not otherwise be covered in your day-to-day. 

📚 Read our Employee's Guide to One on One Meetings.

Since the one on one is private, it’s also a chance to discuss more personal issues that shouldn’t be discussed around other team members. This could include topics surrounding your job role, your performance, professional development, where you see yourself in the future, and more. 

  1. Are there any tasks you feel I am neglecting?
  2. What specific goals should I work toward in order to improve my performance?
  3. What could I focus more of my time on? 
  4. What would you like me to focus less of my time on?
  5. What can I do to make your job easier?
  6. Is there anything I could do to communicate with you better?
  7. Is there anything more my team needs from me?
  8. Do you believe I am making progress on my goals?
  9. What are your top priorities for this month?
  10. What are your top priorities for this quarter?
  11. How can I better support the new members of our team?
  12. Is there room for me to grow within my current role?
  13. Do you feel like the business is on track to meet this year’s goals?
  14. What personal goals do you hope to accomplish in the next 6-12 months?
  15. What’s one specific thing I could work on between now and our next meeting?

15 Questions to ask your boss in a performance review

Performance reviews provide a similar setting, but they are a bit more formal and far less frequent than one on ones. 

During your performance review, keep your questions a little more formal and directed at your career specifically. This is also an ideal time to ask broader scale questions about your own direction and the future of the company. 

  1. Where do you feel my strengths lie?
  2. What do you feel are my greatest strengths within my role?
  3. What else could I be doing to help the team succeed?
  4. What else could I be doing to help the business succeed?
  5. How can I better support my team?
  6. What professional development opportunities are available to me?
  7. What opportunities for growth are available to me?
  8. Am I meeting your expectations in my role?
  9. How are you hoping I will grow within the company?
  10. What do you think is the company’s greatest challenge moving forward?
  11. Is there anything you’d change about our company’s culture?
  12. What goals are you currently working toward?
  13. What are your top priorities for this year?
  14. Where do you see the company 10 years from now?
  15. This is where I see myself in 5 years; how do you see me getting there?

10 Questions to ask your manager or boss in casual conversation

There’s one final type of question we want to cover—the casual and engaging questions that will help you get to know your boss. If you work in a physical office, some of these might be reserved for moments when you cross paths with your boss during a break or before a meeting.

You can also save a few casual questions for the beginning of your one on one meetings to break the ice. Intriguing or lightly personal questions will help you get to know your boss on a deeper level, and they will help you continue to build rapport.

Remember to personalize these questions when possible based on what you already know about your boss. In order to do this successfully, you must deeply listen when they answer your questions, and you must remember their answers. To help you remember, after the meeting, jot down a few notes that you can refer to before your next one on one. What book/tv show/movie/podcast did they mention? What hobby did they talk about working on? Did they discuss recently coming back from a vacation or going on one soon? Any details you can remember will help you craft personalized questions for your next meeting.  

  1. What are your plans for X holiday?
  2. Do you have any time off planned soon?
  3. What’s the last book you read?
  4. Do you have any movie, TV show, or podcast recommendations?
  5. What’s your favorite restaurant in town?
  6. If you could only eat one food for the rest of your life, what would it be?
  7. If you could become an expert at something right now, what would you choose?
  8. What are your ideal working conditions like?
  9. If you could teleport to anywhere in the world, where would you go? 
  10. When you were a kid, what did you want to be when you grew up? 

Clear communication with WorkPatterns

WorkPatterns provides One on Ones, Team Collaboration, Feedback, Recognition & Goals — all in one place. Use our platform to save and manage meeting questions, schedule with clarity, and set action items after each meeting. With WorkPatterns, your list of questions is always available in the private notes tab of your workspace, so you’ll be prepared with engaging questions for your boss no matter the meeting.

If you have any questions or content requests, reach out to our team at any time.

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