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140 Questions To Ask A Boss (Ace Your Next Encounter!)

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Questions are a valuable tool in the workplace. By asking your boss the right questions, you can gain insight into what they value and how to advance within your industry. 

20 Best Questions to Ask Your Boss to Help Your Career

As you prepare to meet with your boss, jot down a handful of questions you feel would help you. Some of these questions can help you understand your boss better, while others will help them see your desire to grow professionally.

  1. What new and exciting developments are happening in the company, and how does my role support those? It can be helpful to get a bigger picture view of what you are doing at a company. 
  2. What resources are available through the company to help me grow and develop professionally? Try to keep a broader view of the work you are doing. Let your boss know what big-picture goals you have for your career and see how they are able and willing to help you achieve them. 
  3. What does an ideal workflow look like to you? Some bosses want to be more hands-on, while others may only ask you to come to them with questions or an occasional check-in. Communicating ahead of time can help minimize miscommunications and consequent stress. 
  4. If money were not an issue, what roles would you hire in the company, and what projects would you invest in? This question can help you see insight into what your boss values within the company and what direction the company will likely move towards in the future as funds become available. 
  5. How would you recommend I reach [your career goals]? By asking your boss to help you with professional development, you’re essentially inviting them to become a mentor. Your boss will likely have a network and other resources they may be able to offer you to help you reach your goals. 
  6. Are there any aspects of my work that you want to see change? This is quite direct and can therefore be stressful to ask. But it can be helpful to get concrete feedback on what you are doing well and where your boss would like to see improvement. 
  7. I’m feeling overwhelmed by [specific area/project]. Are there ways you can help me?If some projects or responsibilities regularly stress you out, be sure to bring those up and have an honest and open conversation with your boss about them. Who knows—the tasks that may be stressing you out may be a good fit for someone else on your team. 
  8. Are there any thought leaders within our industry that you recommend I learn about and study what they’re doing? Find out if there are people you should learn from that you may not already know about. Your boss has likely been in the industry for longer than you and can offer you direction on who to look into. This question also shows initiative through asking, an interest in learning more, and a willingness to work on your own time. 
  9. How do you find a healthy work-life balance? Knowing when to call it a day is important, and going home to your life outside of work is important. Letting your boss know that you struggle with clocking out can help them understand how to encourage you. Workers who have a healthy work-life balance are more likely to stay with their current company, according to a recent survey of over 13,000 US workers. Hopefully, your boss will support your desire for work-life balance. 
  10. Are there tools we have that I am not utilizing to their fullest potential? Your company likely has project management tools and other resources for the workplace that you may not be utilizing to their fullest potential. Learn from your boss and see if there are features or methods you may not have known. 
  11. What are some of the benefits our company offers that you enjoy taking advantage of? It’s not uncommon for companies to offer benefits to help their employees thrive in and outside the workplace. Make sure you’re taking advantage of them by asking your boss what they enjoy about the workplace benefits. 
  12. What definition of success do you use for yourself? This question can be incredibly insightful in seeing what your boss values. 
  1. I would like feedback on [specific project or task]. When would be a good time for us to talk about that? If you’re able, give your boss a heads-up if you want feedback on a specific area of your work. This will allow them to review your work and offer you helpful feedback. 
  2. How would you describe our organization’s mission, vision, and values? This can be a springboard for a conversation about the philosophy behind your organization and help you align what you’re doing with the company’s bigger picture. 
  3. I’m a little bit confused about [specific task or project]. Could you give me an example or offer further clarity? Don’t be scared to ask your boss for clarity! Before asking them, read any resources or directions they sent you. In the long run, asking for help will save everyone’s time. 
  4. Why did you choose to hire me? This question can help you gain insight into what needs the team you’re joining has and what strengths your boss saw in you during the interview process. 
  5. When there is disagreement within the team, how would you like to handle it? It’s almost inevitable that there will be disagreements within a team. Find out before they happen if your boss would like to be involved from the beginning or if they would like you to handle it on your own as much as possible. 
  6. What do you see as your greatest strength? This question can help you get to know a new boss better quickly. Gain insight into how they lead and what qualities they value in themselves. 
  7. If I eventually want to work in a leadership role similar to yours, what would you recommend I do over the next year to stand out from others? Ask your boss for advice if you’re interested in being promoted to a similar position as them! They will be one of your best resources to learn what they did to set themselves apart from the competition. 
  8. What’s something you’re excited about? Remember, your boss is a person, too. Show that you are genuinely interested in what is going on in their life! 

Ready to level-up your life? Watch our video below to learn how to create your own professional development plan:

Questions to Ask Your Boss to Build Rapport

If you’re ever nervous while standing next to your boss in the break room or while driving to meet with a client, try asking them a few questions that will help you get to know them better.

  1. What do you do for fun on the weekends?
  2. Have fun plans for the holidays, summer break, or your upcoming vacation?
  3. How is your child, spouse, or baseball league?
  4. I have a big dinner for my anniversary, do you have a favorite restaurant in town?
  5. Do you have any big goals coming up? Can I help in any way? This is especially great to ask around New Year or a birthday.
  6. Do you have a favorite holiday? Does your family have any traditions for celebrating it? 
  7. What sports do you follow? 
  8. Is there anything you’re studying or learning right now? 
  9. Have you ever played an instrument? 
  10. What’s something that happens in the day-to-day life that brings you joy?

Questions to Ask Your Boss About Expectations

Whether you’re stepping into a new role or your current organization is undergoing some restructuring, it’s good to ask your further boss questions about expectations. 

This can help you feel confident in what tasks you prioritize, how you structure your time, and what they value. 

  1. What would success in this position look like in the first 3 months? 
  2. How would you describe your management style? 
  3. How would you describe the team dynamic here? 
  4. What do you feel I bring to the team? 
  5. What changes would you like to see within the team and our work over the next 6 months? 
  6. What are 3 things you wish you could change about how the team collaborates? 
  7. How regularly do you want to receive progress updates on the tasks I’m working on? 
  8. What does good leadership mean to you? 
  9. What’s a professional achievement you’re proud of? 
  10. What do you believe is the most important skill to have within this industry? 
  11. What is the best way for me to ask you for feedback on my work? 
  12. What is the best way for me to reach or communicate with you? 
  13. What changes do you envision happening in our team in the near future? 
  14. Are there additional tasks you would like to see me take on? 
  15. How do you see my background and experience contributing to this team?
  16. What is something I am doing well that I should continue to do? 
  17. What is something I am not doing well, and how can I improve in that area? 
  18. Can you rank my current responsibilities in order of highest to lowest priority? 
  19. What strengths do you value the most in a direct report?  
  20. What are your goals for this coming quarter? 
  21. What form of communication would you like me to use when giving you status updates? 
  22. How often would you like to have one-on-one meetings
  23. How often should I expect to have team meetings? 
  24. Are there any projects you wish I took more ownership of? 
  25. Are you open to new ideas and feedback, and how would you like for me to present those to you? 

Questions to Ask Your Boss About Your Future

Your boss is an excellent resource for information about your future. They have likely sat where you are today and can help guide you toward future opportunities. You may ask them questions regarding the specific growth opportunities within your company or for broader guidance within the industry you work in. 

Remember: the more your boss knows your career goals, the more they will be able to help you achieve them. 

  1. Are there tasks you would like to see me take on that I currently am not? 
  2. What development and growth opportunities can you recommend I take advantage of? 
  3. What are your career goals? 
  4. What would you recommend I do this month to increase my chances of getting promoted in the future? 
  5. Based on your experience working with me, are there positions within the company that you believe I would thrive in? 
  6. What advice would you give me at this point in my career? 
  7. What career choices did you make at this stage that you look back on as having a pivotal impact? 
  8. Do you have any regrets about your career journey or aspects you wish you had handled differently? 
  9. Do you think I should lean into my strengths more or work on developing my weaknesses more? 
  10. What is the most important soft skill in this industry? 
  11. Do you have any people in your network doing what I hope to do in my career that you would be willing to introduce me to? 
  12. What is the biggest lesson you have learned throughout your career? 
  13. What have you had to sacrifice in your personal life to achieve the career space you are in currently? 
  14. How much opportunity for advancement is there within this company? 
  15. If I want to reach [your career goals], how long do you estimate it will take? 
  16. Do you feel [your company name] is the best place for me to invest my time and energy if my long-term goals are [your career goals]? 
  17. I’m not sure yet what my 5-year goals are with my career. Can you help me understand more about the various routes and options I have within the industry? 
  18. What networking events would you recommend I prioritize attending? 
  19. What are the most exciting developments within our industry over the past decade? 
  20. Are there any new members of our team I can help train? 
  21. I would love to work in a leadership role in the future. Do you have any recommendations for how I can prepare myself today to be ready for that? 

Questions to Ask Your Boss in a Meeting 

These questions can help start conversations about team members’ strengths, improve the atmosphere in the workplace, and help your team think creatively when faced with unexpected difficulties. 

  1. What three things do you think we are doing well that we should continue doing? 
  2. What is something you think we should prioritize improving on? 
  3. In what way do you feel we contribute to individuals’ well-being through the work we do? 
  4. What unique strengths does each individual bring to the team, and how can we switch around tasks to maximize those strengths? 
  5. What is the big-picture purpose of our team’s role within the company? 
  6. What safety nets can we implement to help prevent burnout? 
  7. What do you attribute past success to, and are there ways we can replicate it in our current projects?
  8. What upcoming projects are you most excited about? 
  9. What makes you excited about working for this company? 
  10. What is something we do differently than our competitors? 
  11. What is a project you have loved working on in the past, and how can we make our current projects similar to that? 
  12. What areas do you feel we’ve improved as a team over the past year? 
  13. What helps you feel motivated? 
  14. What is something small we can do today as a team to help everyone feel valued and appreciated? 
  15. What creative approaches have we not yet tried for solving [a specific problem]? 
  16. Is there anyone in our company we could bring on as a consultant for [specific challenge your team is facing]? 
  17. What other tools and resources have we not yet considered using to navigate [specific problem]? 
  18. How can we show appreciation for the hard work of other teams we are collaborating with? 
  19. What are our sales goals for this quarter, and how close are we to reaching them? 
  20. What does company appreciation for reaching sales goals look like? 

Questions to Ask Your Boss in a One-on-One 

A one-on-one meeting is your opportunity to talk about anything that is on your mind with your boss. It is important to come prepared to utilize this time to the best of your ability. 

Remember, a good boss is on your side. They want you to thrive in the workplace, feel fulfilled with the work you do, and help mediate any conflict that may be happening. 

  1. Can you recommend any books or resources I should study to help me become more knowledgeable about this field? 
  2. What are 3 things I’m doing well that I should continue doing? 
  3. What are some ways I can improve as a team player?
  4. What are some ways we can improve our workflow? 
  5. What hard or soft skills would you like to see me strengthen between now and our next meeting? 
  6. In what ways do you see yourself uniquely equipped to support me and help me develop professionally? 
  7. What additional responsibilities can I take on to help me develop my resume and have the opportunity to grow into another position in the future? 
  8. Are there decisions you made within your career that you wish you had done differently? 
  9. If you were currently in my position, what “next moves” would you make to open up new opportunities for yourself? 
  10. How can I invest in developing my potential? 
  11. Is there anyone at the company you think I can learn a lot from, and would you be willing to introduce me to them? 
  12. What made me stand out from other applicants you interviewed for this position? 
  13. Do you feel I contribute much in team meetings, or do you wish I shared more or less? 
  14. What’s an example of a situation I handled well or poorly in the past 2 weeks? 
  15. Would you like our one-on-ones to focus on long-term growth or immediate change? 
  16. Are there any local initiatives or nonprofits that the company contributes to? 
  17. How would you define failure? 
  18. How much freedom and flexibility do I have to be innovative with [specific task]? 
  19. Would you be open to having me take on more of [a task you enjoy]? 
  20. Is there anything outside of work that you’re looking forward to this week? 
  21. If there was 1 thing you could change about our workplace, what would it be? 
  22. Is there flexibility to work from home, or do you prefer everyone to be in the office? 
  23. Does our team’s approach to problem-solving and working on projects make sense? 
  24. How do you navigate negativity from others? 

Bonus: 20 Questions to Ask If You’re the Boss

What if you’re on the other side of the table in a one-on-one meeting with your employee? Ideally, your employee will come up with a list of great questions to ask, but there are certain topics that your employee may feel awkward bringing up. 

Here are some helpful questions to ask to help foster openness:

  1. How can I help and support you? 
  2. What are your personal and professional goals for the coming months, and how can I help you achieve them? 
  3. Are there areas of communication you feel that the team as a whole or I could improve on? 
  4. Are there any tasks or responsibilities you currently have on your plate that you wish you weren’t responsible for? 
  5. If you were responsible for hiring new team members, what position would you hire next for our team?  
  6. What, if anything, in either your role or the team as a whole that is stressing you out? 
  7. Do you ever wish I was more involved in your day-to-day work? 
  8. If you were in my position, what is one thing you would change about how our team runs? 
  9. Do you feel clear and confident about what is within your scope of responsibilities, or can I help answer any concerns or clarify any questions about your role? 
  10. What do you enjoy most about your work, and are there ways we can ensure you do more of that? 
  11. Are there any activities you think would be fun to do as a team that could improve our dynamic? 
  12. Do you feel you have a healthy work-life balance? 
  13. Are there any tasks you are regularly responsible for that you strongly dislike doing? 
  14. What’s something you are proud of that you worked on or completed this past week? 
  15. What are your career goals for the next 5 years, and how can I support you in reaching them? 
  16. Are there aspects of my leadership style that are challenging for you? 
  17. What would your ideal task list look like?
  18. Who from our team do you feel is doing an exceptional job and should be recognized for their work? 
  19. Do you see any bottlenecks on our team that, if cleared up, would help us accomplish our goals more seamlessly? 
  20. Do you have any creative solutions to the challenges we are experiencing as a team? 

If you’re the boss welcoming a new employee to the team, read our article on How to Welcome a New Employee to The Team (The Awesome Way)

Final Thoughts: Things to Keep In Mind as You’re Prepping for a Meeting 

When you’re getting ready for a meeting with your boss, try to plan and have several questions prepared that you’d like to ask them. 

Here are a few tips to keep in mind as you head into a meeting with your boss: 

  • Get ready ahead of time. If you’re able, start thinking about what you’d like to discuss with your boss a few days before the meeting. Depending on your boss and their communication style, they may want an agenda beforehand to know how to prepare for the meeting.
  • Overprepare and then prioritize. In a meeting, you will likely only have time to ask a handful of questions. Before going into the meeting, know what you care about the most. For example, do you want feedback from your boss on how you approach projects and their preferred communication styles? Focus on questions related to those topics. On the other hand, if you’re more concerned with learning to progress within your industry, focus on more personal development questions. 
  • Remember, this won’t be your last meeting. When meetings don’t go how you anticipate, it can be discouraging. Remember, you can always email your boss and ask to schedule another meeting. Let them know you didn’t have a chance to review a few questions you had for them. Then, ask if they have any other availability over the coming weeks. 
  • Drop a complimentary “why.” People love receiving compliments! Giving a genuine compliment as a part of your question can be a great way to strengthen the relationship. Let your boss know why you’re asking them a question, and don’t miss the opportunity to say something nice. For example, instead of asking, “Do you have any people in your network you could connect me with?” Try, “I know you’re a charismatic and well-connected person in this industry. Are there any people you would be willing to connect with whom you think I could benefit from talking to?” Or, instead of, “What advice can you give me from your career journey?” try, “I really admire the work you’ve done through [name a specific project they were in charge of]. I would appreciate any insight you can give me on your career journey and how I can make similar strides.” 
  • Express gratitude for constructive criticism. Constructive criticism can be challenging to hear, but it is one of the quickest ways for you to receive feedback and grow. Everyone can improve in their role at work. If your boss offers you feedback, remember to thank them! 

Do you have a meeting around the corner that you’re nervous about? Check out our article 6 Tricks to Prepare For a Meeting (& Conquer Glassophobia)

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