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.
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.
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 Charma, 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.
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.
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.
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.
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.
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.
Charma is the best practice toolkit for managers to organize, motivate, and engage their teams, beloved by managers, HR, executives, and ICs alike. Find tools to help manage agendas for one-on-one meetings and team meetings, action items, team collaboration, continuous feedback, recognition, and 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 Charma, 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.
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