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Questions to ask your boss: get what you want and feel you deserve

Questions to ask your boss: get what you want and feel you deserve

Artwork by: Seva Vyvodtsev

  • Why you should be asking your boss questions
  • Things to do before asking questions
  • When is a good time to ask questions?
  • One-on-one meetings
  • Casual encounters
  • Networking and professional development
  • What are some smart questions you should ask your boss?
  • 10 Questions to ask in a one-on-one meeting
  • 10 Questions to ask in a performance review
  • 10 Questions to ask a new boss
  • Key takeaways

You might be hesitant to ask your boss questions, but it’s actually expected, and in most cases, welcomed. In this article, we’ll discuss the best questions to ask your boss to improve your professional relationship and get the most out of your career.

Most of us spend our whole life asking questions: why is the sky blue? What does a yellow light mean? Do I have something stuck in my teeth? But when it comes to the workplace, sometimes we’re hesitant to speak up, either because we don’t want to be a “bother” or we’re afraid we’ll look incompetent. Asking the right questions of your boss will enable you to perform your job better, open the lines of communication with your manager, and help you climb the corporate ladder. 

Ideally, you’ll have a manager who encourages effective, honest communication, and asking him or her the right questions helps you set the right goals, understand what's expected of you, and show you how you can improve and grow. Having productive conversations with your boss will help you gain insight into your career in a way you might not achieve on your own.

In this article, we'll break down the why, whens, and hows of asking your boss pertinent questions to help you get the most out of your career:

  • Why it's important to ask questions of your boss

  • When should you ask questions

  • What questions should you ask your boss

Why you should be asking your boss questions

First of all, let's get one thing straight: it's perfectly okay to ask your boss questions. Done properly, it's not only expected, it's most likely welcomed. An employee who understands their job, goals, and how they contribute to the team as well as the company is going to be more productive. You're not going to be following your manager around like a toddler, screeching, "Why? Why? Why?" Asking smart, well-timed, and relevant questions will help you thrive, and we promise won't annoy your boss.

Remember, it's important to cultivate a positive relationship with your boss. You're not "sucking up," you're building rapport and demonstrating your interest in and commitment to your job. It's your boss who will be evaluating you and delegating work, and often is the person who sets you up for a promotion. By asking the right questions (at the right time) you'll show them that you are enthusiastic about your job and committed to your career growth.

Expert Tip

Take your time in formulating your questions. Your boss is as busy as you are (probably more!), so time is at a premium. Your questions need to be thoughtful, reflective, and well-timed. Peppering your boss with questions all day can be detrimental to your career, especially if your boss decides they need to avoid you to get their work completed.

Things to do before asking questions

To ensure that your questions are necessary, there are a few things you should do before bringing them to your boss. Asking a question that is answered in your employee handbook, for example, or that was presented at the last team meeting will make it look like you’re either not paying attention or that you’re trying to get face time with your boss just for the sake of attention. Before taking something to your boss, try these tactics first:

  • Try to figure it out on your own. If it's a task you need help with, see if you can figure it out. Check your notes or handbook, or just take some time to work through it. But if it's taking much longer than it should, or you just can't get it, then it's time to ask for assistance or clarification.

  • Prepare your questions ahead of time. You don’t want to sit down in front of your boss and all of a sudden, have your mind go blank. Getting your questions in order in advance will allow you to gather any supporting information to show your boss that you’ve tried to figure things out on your own.

  • Approach your boss politely and professionally. You wouldn't corner them in the restroom with a laundry list of questions, but you still want to make sure you're not ambushing them when they don't have the time. If they're in their office (and not on the phone) you can ask them if they have a moment, or you can send a brief email, asking for a short meeting, giving them an idea of what you'll be asking them and how much time you need.

When is a good time to ask questions?

When you’re looking to ask your boss questions, be aware of the demands on their time. Just like you, they have a lot of balls in the air, and if you catch them in a bad moment, it can create an uncomfortable encounter or give the impression that you don’t respect their time. If you’re looking for an impromptu meeting, make sure they’re free, or schedule something on their calendar if that’s what they’d prefer. 

While it’s fine to regularly ask insightful, useful questions, don’t go overboard. You’re not the only person your boss encounters during the day, so make sure your questions are concise, relevant, and helpful. And make sure your questions have a purpose, even if it’s to build a positive relationship and rapport with your boss. 

Statistical Insight

According to a recent study by Leadership IQ, there is a direct correlation between employees "who spent more time with their managers with higher levels of inspiration, engagement, innovation, and intrinsic motivation — to a point." Those who spent six hours interacting with their boss were 29% more inspired in their work,30% more engaged, 16% more innovative, and 15% more intrinsically motivated. More than six hours, however, resulted in "diminishing returns."

One-on-one meetings

If you work for a company that has regularly scheduled “one-on-ones” with your boss, that’s the perfect opportunity to ask questions about your position and responsibilities and the company, as well as casual questions to build rapport with your boss.

If your company doesn't provide weekly check-ins, you might want to suggest a monthly, informal performance review with your boss. You might feel like you're deliberately putting your feet to the fire, but it will not only give you a regular outlet for your questions, it will allow you to give insight into any issues that might come up in your formal evaluation and give you time to make the necessary adjustments.

It's important to note that if you have a significant concern or problem, set up a time to talk to your boss sooner rather than later. An effective manager will make room in their schedule to answer your questions, no matter how busy they are, in order to be more productive and maintain a positive work environment for the whole team.

Casual encounters

If you're making a coffee or sandwich run, consider asking your boss to "tag along." The encounter will be more casual, and you might not have time to present your questions, but it will still be a good opportunity to develop your professional relationship.

These casual meetings are a good place to ask informal questions that you might not have time for in a performance review or a scheduled one-on-one meeting, such as:

  • What are your ideal working conditions?

  • What did you want to be when you were a child?

  • What’s your favorite restaurant?

  • Any plans for the upcoming holiday?

  • Are you going anywhere interesting for your vacation?

  • What’s the last book you read?

Networking and professional development

There's a good chance your boss would welcome the opportunity to attend a networking event, and it would allow you to discuss your questions in a professional setting. Your boss may also be aware of company-sponsored, non-mandatory events that can be good opportunities to meet people within your organization that you might not otherwise have the chance to interact. And you might learn something, too!



Remember that you have other resources other than your boss. Interacting with colleagues shows your willingness to collaborate and build team relationships.

Ask the same question twice. Unless you truly don’t understand the answer, it will appear that you don’t care, or that you weren’t paying attention.

Wait until your boss isn’t busy. This way, they can focus on you and give you a less-rushed, more helpful response.

Ask questions that can be easily answered with an internet search.

Respect your boss’ communication preferences. Some are okay with a quick drop-in chat, others prefer email or a DM.

Ask about co-workers unless it's affecting your job performance.

What are some smart questions you should ask your boss?

If you have the chance to ask your boss your questions, deciding exactly what questions to ask depends on your circumstances. In general, asking questions provides multiple advantages: it can help you get feedback, gain a clear understanding of your goals and expectations, and receive insights into company performance and overall goals. But some questions work better in individual settings, whereas others can be more casual or “on-the-fly.”

Other benefits of asking appropriately-timed questions are

  • The opportunity to demonstrate your knowledge and expertise

  • Learning how to develop professionally and learn new skills

  • increase your chances of getting a promotion or a salary increase

  • Improved fellowship and rapport with your boss

  • A clearer understanding of your motivations and work style

  • It allows you to show your knowledge and expertise to your manager

10 Questions to ask in a one-on-one meeting

One-on-one meetings are the best time to ask questions. It’s a time that the boss has set aside just for you, and to focus on your performance. It also allows your manager to get to know you better, and in this type of scenario, the boss might have answers to questions you didn’t even think to ask!

One-on-ones are also, by their very nature, private, which allows you to talk about issues that you might not want to share with your co-workers, including questions about your performance, position, professional development opportunities, salary expectations, career plans, and so on.

  1. What’s something I can work on in the near future?

  2. Is there a way I can improve communication with you?

  3. What can I do to make your job easier?

  4. Is there something I’m not doing that would be beneficial to the team?

  5. Am I making appropriate progress in my role?

  6. What are your top goals for this month/quarter/calendar year?

  7. What things should I focus more/less on?

  8. Is the company on track to meet its yearly goals?

  9. How can I grow in my current position?

  10. How can I better support you as well as the team?

10 Questions to ask in a performance review

Performance reviews are similar to one-on-one meetings, but they are more formal and occur only once or twice a year. There is generally also mandatory paperwork and forms that go along with a performance review, and areas that the boss is required to cover. In this situation, you'll want to keep your questions more career-oriented, keeping in mind the "big picture" of your professional development as well as the company in general. Many of your questions might be answered while your boss is reviewing your evaluations, so make sure you check them off your list before you ask.

  1. What do you think my greatest strengths/weaknesses are?

  2. What can I do to better support the team?

  3. How can I progress within the company?

  4. Are there any professional development opportunities you would recommend?

  5. Am I meeting expectations for this position?

  6. What are your goals for this quarter/year?

  7. What are our team’s top priorities?

  8. How do you feel about the company culture at the moment? Is there anything you’d change/improve on?

  9. My five-year plan is X; how can I best reach those goals?

  10. Where do you see the company going in 10 or 15 years?

10 Questions to ask a new boss

Even if you're a seasoned professional, getting a new boss, whether it's because you're new to the company or they are, can be cause for anxiety. Getting to know your boss and setting yourself up for success is important. Every manager you'll have will be different, whether they're gregarious, outgoing, and hands-on, or quiet, serious, and reserved. While there's no magical modus operandi for working harmoniously with a new boss, it's helpful to ask the right questions to get off on the right foot. Here are ten questions you might want to ask:

  1. How do you prefer to communicate with your employees?

  2. What’s the best way to ask for/give input and feedback?

  3. What would you do if you were in my position at this company?

  4. What is the most important thing you hope to accomplish in your new position?

  5. What are your career goals?

  6. What does your boss think is their top priority?

  7. What can I do to make you more successful at your goals today/this month/quarter/year?

  8. What do you like best about your job?

  9. Can you tell me about your work/management style?

  10. What made you decide to hire me?

 It's important to remember that your boss is a human being, and wants you to succeed. A good boss aims for his or her employees to thrive, be engaged, and feel productive. And consider that you'll have more than one opportunity to ask questions, so don't feel pressed to get them all answered in one session. 

It's not always easy, but asking the right questions and maintaining open lines of communication with your boss will help you maintain a good work environment. It will also help ensure you're on the right track, so there are no surprises come annual review time. The bottom line, asking questions might just be one of the best things you can do for your career.

Key takeaways

  1. Asking the right questions of your boss will enable you to perform your job better, open the lines of communication with your manager, and help you climb the corporate ladder.

  2. It’s perfectly okay to ask your boss questions. An employee who understands their job, goals, and how they contribute to the team is going to be more productive. 

  3. Make sure your questions are concise, relevant, helpful, and have a purpose.

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