108 Powerful One-to-One Questions Managers Should Ask

One-on-one meetings are an essential part of manager and employee relationships. They provide a time for both parties to share feedback, check in on mental health, and discuss the big picture. However, many managers and employees struggle with what questions to ask during these meetings. This blog post will provide powerful questions managers can ask in one-to-ones that can help improve employee relationships!

Growth and Development Questions for Managers to Ask During One-to-Ones
Questions to Improve Communication
Manager One-to-One Questions for Motivation
Ask These Questions to Address Challenges and Roadblocks
Managers Get Actionable Feedback With These Questions
Improve Productivity With These Questions One-to-One
Questions for Managers to Ask at the End of a One-to-One

Why are productive one-on-one meetings important?

One-on-one meetings are vital because they allow both the manager and the employee to share feedback, check in on mental health, and discuss the big picture. As a result, they help to improve communication and collaboration between the two parties. In addition, one-on-one meetings can help identify potential issues early on and prevent them from becoming more significant.

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Productive one-to-one meetings are crucial to maintaining strong manager-employee relationships. By asking the right questions, managers can gain valuable insights into their employees’ thoughts and feelings. This helps to create a more open and understanding relationship between the two parties. This can lead to improved communication, collaboration, and overall productivity.

How to Prepare for Your One-On-Ones

One-on-ones are a great way to build a relationship with your employees and ensure they feel comfortable coming to you with any issues or concerns they may have. They can also be a great way to get feedback from your employee on their work and to discuss any challenges they are experiencing.

To prepare for your one-to-one, determine what you want to discuss. Next, you should review the employee’s goals and objectives for the quarter and see how they are doing in meeting them. You can also use this time to discuss challenges and brainstorm possible solutions.

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In addition, it is often helpful to prepare a list of questions you can ask your employee. This will help keep the discussion flowing and help you get the most out of your one-on-one.

Why do managers need to ask the right questions during one-on-ones?

Managers who ask the right questions during one-to-one meetings can build trust, develop better relationships, and get to the root of problems. Employees who know that their manager is interested in their well-being and wants to understand them as a person will be more likely to be open and honest. Asking the right questions also allows managers to get feedback and gain insights that they can use to improve their team’s performance.

One of the critical benefits of asking the right questions during one-to-one meetings is that it can help improve employee relationships. When employees feel that their manager cares about them and is interested in their well-being, they are more likely to be open and honest. This, in turn, can lead to better communication and a stronger working relationship. Additionally, when managers get feedback from employees, they can use this information to improve team performance.

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Why do managers find it difficult to ask the right questions?

One reason managers find it difficult to ask the right questions during one-to-one meetings is that they may not know what to ask. Additionally, some managers may feel uncomfortable discussing personal topics with their employees. They may also be afraid of asking difficult questions and getting negative feedback.

Managers who take the time to prepare for their one-to-ones will be more likely to ask the right questions. By thinking about the topics they want to cover, they can develop specific questions to help them get the information they need. Additionally, managers should ensure they are comfortable discussing personal topics with their employees. This will help them to create a more open and trusting relationship. Lastly, managers should be prepared to ask difficult questions and be willing to listen to the feedback that they receive.

Powerful Questions Managers Should Ask In One-On-One Meetings

One-on-one meetings allow managers to check in on their employees’ progress, give feedback, and address any challenges that may have arisen. While the discussion topics during these meetings can vary, there are powerful questions that managers should ask to get the most out of these one-to-ones.

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Growth and Development Questions for Managers to Ask During One-to-Ones

  1. What professional goals would you like to accomplish in the next 6 to 12 months, and what makes you say that?
  2. What has been the work highlight/lowlight from the past week?
  3. Are there any new skills you’d like to learn?
  4. Who’s someone in the company that you’d like to learn more from?
  5. What other roles here do you find interesting? What skills do those roles require that you would like to work on?
  6. What part of the business would you like to learn more about?
  7. What projects would you like to work on or be more involved in?
  8. What’s one thing you’d like to do more of outside of work this coming month?
  9. In your view, how have you grown since working here?
  10. Are you interested in any conferences or courses? Are you open to recommendations?
  11. What’s something you’re itching to try that you haven’t had the time or resources to do?
  12. How do you feel like you’re trending on your growth goals?
  13. Are there any specific software or tools you’d like to learn how to use?
  14. Is your job what you expected when you accepted it? If not, where has it differed?
  15. What are your work and non-work highlights of the past month?
  16. What else can I be doing to help progress your career?

One-to-One Questions for Managers to Ask That Improve Communication

  1. Who is doing a great job on the team? What have they done?
  2. What’s one thing we can do to improve the performance of the team?
  3. What needs to change around our team meetings?
  4. Where has our communication faltered? Can you give me an example?
  5. What do you like about our one-on-one meetings? What can be improved?
  6. Are you happy with our level of communication? How would you change it?
  7. Are there any roles on the team that you feel unclear on?
  8. Is there anything that would be productive for me to re-explain to our team?
  9. Which team members do you wish you had more of a connection with?
  10. Am I providing enough clarity on our direction?
  11. If you were managing the team, what would you do differently?
  12. Where would you like me involved more in your day-to-day? Where would you like me involved less?
  13. Am I acting like the best manager you could wish for? What could I be doing better?
  14. Do you feel like you’re able to stay connected with everyone? Is there anything I can do to help?
  15. Do you feel like the team is communicating effectively enough? If not, what’s standing in the way?
  16. What can I hold you accountable for the next time we talk?
  17. What’s top of mind now that we haven’t talked about yet?
  18. Do you have any questions about the recent change involving X?
  19. How could we improve cross-functional collaboration?
  20. When’s the best time to give feedback on your work?
  21. Do you feel like you’re able to ask others for help? Why or why not?
  22. How confident do you feel about where the company is going?
  23. How aligned do you feel with where the company is going?
  24. What’s a problem we have on our team that I might not know about?
  25. Is there a problem on the team that I might not know about? What is it?
  26. What are your top priorities this week?

Managers Improve Motivation by Asking These Questions in One-to-Ones

  1. What are you passionate about, personally or professionally?
  2. On a scale of 1-10, how happy are you at work?
  3. Do you feel like you’re able to disconnect after work? Why or why not?
  4. How are you feeling?
  5. How do you feel your work/life balance is? What would you want to change, if anything?
  6. Do you find your physical work environment productive? Is there anything preventing you from being productive?
  7. What’s one thing we could change about work for you that would improve your personal life?
  8. What’s something past managers have done that’s frustrated you?
  9. Are you happy in your role? What could make it better for you?
  10. Are you proud of the work you do here?
  11. Are there any goals we have on a company, team, or individual level that you feel are entirely unattainable? If so, why?
  12. What were your work and non-work highlights last week?
  13. Which one best describes you during the past month?
  14. Is there anything stressing you out right now? What is it?
  15. What does an ideal, productive workday look like to you? Walk me through it.
  16. What’s something you’re proud of that happened this week? This month?
  17. What’s the best thing about working here?
  18. What’s one thing you would recommend to improve our workplace culture?
  19. What do you wish I did less of? More of?
  20. Who on our team deserves a shoutout for their work and why?
  21. If you were the CEO, what’s the first thing you’d change?
  22. What makes you excited and motivated to work on a project?
  23. How are you feeling about your goals?
  24. What’s your least favorite part of your day-to-day at work?
  25. What’s something past managers have done that’s inspired and motivated you?

Questions for Managers to Address Challenges and Roadblocks During One-to-Ones

  1. What, if anything, is stressing you out?
  2. What’s something you’d like to share but is a little stressful to bring up in person?
  3. What’s your outlook on next week?
  4. Where do you need help?
  5. What are you least clear about our company-wide strategy and goals?
  6. What do you need? What could make your day-to-day easier?
  7. Do you have any questions that, if answered, would help you in your day-to-day?
  8. What’s one thing I can do right now to make work better for you?
  9. Do you have any questions about what other team members are working on?
  10. What, if anything, feels harder than it should be in your daily work?
  11. If you were a hiring manager for our team, what role would be your next hire?
  12. Do I have anything outstanding for you that I haven’t done yet?

Questions for Managers to Get Feedback During One-to-One Meetings

  1. What is one thing I could experiment with doing differently this month?
  2. Am I doing a good enough job bringing you into team decisions? Would you like to be more involved?
  3. What’s everyone around me NOT telling me?
  4. What is everyone around me neglecting to share with me?
  5. Am I giving you enough feedback on your work?
  6. What can I do to make your life easier?
  7. If I could improve one skill between this meeting and the next, which skill would you choose?
  8. What do you like about my management style? What do you dislike?
  9. Would you like me to share more updates from the leadership team? If so, what kind of information would be helpful?
  10. How would you like me to share feedback?
  11. On a scale of 1-10, how has my level of support/presence been over the past month?
  12. Where do you need support right now?
  13. What “soft skills” do you think I excel at most? What can I work on?
  14. Where do you think I should be focusing more of my attention?
  15. Do you feel like you’re getting enough from our one-on-ones? Why or why not?

Managers Ask These Questions in a One-to-One to Improve Productivity

  1. What has gone well/not so well for you?
  2. Is there anything that frustrates or keeps you from doing your best work? What is it?
  3. What roadblocks can I help you with?
  4. What’s your top priority right now?
  5. What challenges do you face in your role that aren’t visible to others?
  6. What’s one thing (or a few) you learned this week?
  7. What has challenged you?
  8. Do you feel confident in how you/your team are progressing?
  9. What has energized you in your role?
  10. How are you/your team progressing towards established goals?
  11. What’s your outlook on the next week? How about next month?

Questions for Managers to Ask at the End of a One-to-One

  1. What can I help you with between now and the next time we meet?
  2. Is there anything we didn’t cover that you’d like to discuss next time?
  3. What are you committing to between now and the next time we meet?

One-on-one meetings are a critical part of any manager’s toolkit. They allow managers to check in on their employees’ progress, give feedback, and address any challenges that may have arisen. However, managers often find it difficult to ask the right questions during these meetings. As a result, they miss opportunities and derail conversations. Instead, managers should come prepared by thinking about the topics they want to cover. Additionally, managers should ask powerful questions to help them get the most out of these one-on-ones.

Further, managers should ensure they are comfortable discussing personal topics with their employees and prepare to ask difficult questions. By avoiding common pitfalls, managers can ensure that their one-on-one meetings are productive and helpful in building better relationships with their employees.

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Jason Cortel is currently the Director of Global Workforce Management for a leading technology company. He has been in customer service, marketing, and sales services for over 20 years. In addition, he has extensive experience in offshore and nearshore outsourcing. Jason is an avid Star Trek fan and is on a mission to change the universe by helping people develop professionally. He is driven to help managers and leaders lead their teams better. Jason is also a veteran in creating talent and office cultures.

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