Source: https://github.com/chandan-singh/one-on-one/blob/master/README.md Please send pull-requests if you have suggestions to improve.

The one-on-one meetings are vital for organizational growth. Many people-managers overlook the benefits of one-on-one meetings. One of the main reasons is, the manager uses a set of similar 3–10 questions repeatedly. The repetition of questions makes the meeting boring for both, manager and subordinates.

You can easily find many excellent resources and recommendations for the questions that can be used in one-on-ones. Here is the consolidated list of the sample questions which you can readily use in your conversations.

  • What would you like to focus on at this meeting?
  • What were your focus and achievements this week?
  • What challenges or roadblocks do you need help with? Is anything getting in your way lately?
  • Is there anything else on your mind?
  • Is there anything I can do to help you reach your goals?
  • Is there anything that you need from me?
  • What are your plans and priorities for next week? What are you prioritizing and what are you putting on the back-burner?

Short Term (within 9 months)

  • How can we help improve your day-to-day work?
  • How are you feeling about the project?
  • What do you want to work on next quarter?
  • A year from now, what do you want to have accomplished?
  • What do you want to do in your next job/assignment?
  • Are there any skills that you think would be useful for you to acquire in the short term?

Long Term (beyond a year)

  • Where do you see yourself in 5 years? 10 years? 20 years?
  • What work are you doing here that you feel is most in line with your long term goals?
  • What are your long term goals? Have you thought about them?
  • Who do you really admire? Why? (People often admire those they want to become)
  • What are your big dreams in life? Are you making progress on them?
  • What other roles here could you see yourself in down the line? Or what areas would you like to explore?
  • Imagine it’s two years from now, and things have gone well: What has been your role in that? What does your role look like?
  • Have you given any more thought to your long-term goals since our last discussion? What are your latest thoughts?
  • What about this goal is important to you and what will be different when you achieve the goal?
  • In the future, do you see yourself as an individual contributor or in management?
  • What are some things you can start doing in the next 12 months to work towards that goal?

Goal Tracking

  • What skills would you like to work on most right now?
  • Do you feel like you’re making progress on your big goals here? Why or why not?
  • What’s one thing we could do today to help you with your long term goals?
  • Can we do anything to better align your work with your goals?
  • Do you feel we’re helping you advance your career at a pace you would like?
  • Could you see yourself making progress on more of your goals here? What would need to change to do so?
  • What part of your work here are most in line with your goals?
  • What actions will you take before our next 1-on-1 to make progress on X?
  • What sort of progress have you made on the next steps we discussed last time?
  • What have you tried so far to make progress on it? What haven’t you tried yet?
  • What additional resources do you need?
  • What could I do to make you enjoy your work more?
  • Is there a situation you’d like my help with?
  • Have you been struggling with anything?
  • What project do you want to work on next?
  • Are there any projects you’d really like to work on?
  • What additional resources can I provide for you between now and the next time we meet?
  • What are two to three new skills you’d like to learn on the job? What about those skills interests you?
  • How might I make this project more challenging or interesting for you?
  • Which parts of your project are unclear or confusing?
  • What’s something I can start doing to make it easier for us to work together?
  • What can I do to help you feel more engaged at work?
  • What skills/areas would you like to get better at?
  • What have you learned/improved recently?
  • If you were to take a course in something, what would it be?
  • What are some habits/behaviors you’d like to develop?
  • What are some habits that you want to get rid of?
  • Are there any new ideas you’d like to discuss with me/the team?
  • What’s something you’re itching to try that you haven’t had the time or resources to do?
  • Is there anything right now that is slowing you down or blocking you?
  • Are there any obstacles that prevent you from doing your best?
  • When have you felt stressed or overwhelmed in the past month? What can I do to prevent that?
  • What are some recent challenges you’ve faced? How can we work them out?
  • Do I have anything outstanding for you that I haven’t done yet?
  • What area of the company/organization/team would you like to learn more about?
  • Who in the company would you like to learn from? What do you want to learn?
  • Are there any roles in the company you’d like to learn more about?
  • What do you think are the key skills for your role? How would you rate yourself for each of them?
  • What do you think are the key skills for your role? How would you rate yourself for each of them?
  • Are you confused by any part of what you’re currently working on?
  • Do you feel like you’re growing in your role? What makes you say that?
  • What’s working well for you in your current position?
  • Do you feel like we’re helping to advance your career? What else can I be doing to help grow your career?
  • Do you feel like you’re learning at work?
  • Do you feel challenged at work? Are you learning new things?
  • What projects are you most proud of? What do you want to work on next?
  • If you were not a position/role, what do you want to be?
  • What’s a professional development project you’d like to pursue?
  • What skills would you like to develop right now?
  • What are your strengths? What skills would you like to develop?
  • What additional training or education would you like?
  • Are there any events or training you’d like to attend to help you grow your skills?
  • Is there anything I could do to invest more in your growth?
  • What can I hold you accountable for next time we talk?
  • How can I be a better manager?
  • How can I make your work easier?
  • What areas of your work do you want more/less direction from me?
  • How can we improve these 1:1s?
  • How can I better support you?
  • Is there anything I can do to give you more support at work?
  • What is something I could do better? What is the criticism you have for me?
  • What do you like about my management style? What do you dislike?
  • What have your past managers done that you’d like me to also do or not do?
  • What’s something past managers have done that’s inspired and motivated you?
  • What’s something past managers have done that’s really frustrated you?
  • What’s your favorite thing I do as a manager of this team I should keep doing?
  • What would you like to know about me?
  • What feedback do you have for me? Both positive and constructive?
  • Would you be willing to share some feedback on one or two things you think I could do better as your manager?
  • Is there anything you would change about how you and I communicate?
  • Would you prefer more or less direction from me?
  • Do you have some examples of things you think I should have handled differently?
  • Do you have any questions about what I do?
  • What do you think I should know about the project, but might not?
  • Do you feel that I represent the team well to the rest of the company/organization? What would you change?
  • Do you feel like I acknowledge/recognize the positive work that you do?
  • What’s your favorite thing I do as a manager?
  • Can you think of something I’ve done or said recently, that did you didn’t like or agreed with?
  • Is there something I’m doing that I could delegate to someone on the team?
  • Where has my communication faltered? Can you give me an example?
  • Where would you like me involved more in your day-to-day? Where would you like me involved less?
  • What is everyone around me neglecting to share with me?
  • What’s everyone around me NOT telling me?
  • If I could improve one skill between this meeting and the next, which would you choose?
  • Are you happy with your recent work? Why or why not?
  • What is your resentment?
  • What’s not fun about working here?
  • How do you feel about your work/life balance?
  • I’ve noticed you’re a little adjective than usual. Is there anything you want to talk about?
  • What do you want to do but don’t feel like you have the time for?
  • What part of your job do you wish you didn’t have to do?
  • What parts of your job make you unhappy?
  • What’s not fun about working here? What do you enjoy most about working here?
  • How do you feel your work/life balance is right now?
  • What’s something you feel is undervalued that you contribute to the team?
  • Is your job what you expected when you accepted it?
  • What do you feel is your greatest accomplishment here?
  • When was the time you enjoyed working here the most?
  • What worries you? What’s on your mind?
  • Who are you friends with at work? (Shown to be a key to enjoying your job)
  • How is your workload right now?
  • Do you have skills that you think are underutilized at work?
  • What part of your work energizes you?
  • What is your favorite/least favorite thing about your work right now?
  • Which of the least favorite thing affects your overall performance?
  • How is your current work helping or hurting your professional development?
  • What do you feel like you’re learning from this assignment?
  • What are your biggest concerns about your current project(s)?
  • What, if anything, did you used to do that you find you don’t have time for right now?
  • Do you feel that your work is appreciated?
  • How does your work compare to your expectations when first starting here?
  • What are you working on that you don’t want to work on?
  • Do you not want to work on it because you aren’t interested or because you think it’s not important?
  • What would you like to achieve by the end of the year?
  • What’s top of mind right now that we haven’t talked about yet?
  • Are you happy in your role? What could make it better for you?
  • Which one best describes you during the past month? 😀 🙂 😐 🤔 😒 😳 😰 😤

Identify flight risk

  • Are you happy working here?
  • On a scale of 1–10, how happy are you at work?
  • What’s something I could do to get you to a 10?
  • What would convince you to leave for a job somewhere else?
  • Why do you think [employee who recently quit] left?
  • What did they tell you?
  • Is there something we should change?
  • Are you satisfied with your current role, position, and team?
  • Which company values do you like the most? Which the least? Why?
  • What’s your dream job?
  • What kind of a workplace would help you be the happiest version of you?
  • How do you prefer to receive feedback?
  • When’s the best time to give feedback on your work?
  • What’s a recent situation you wish you handled differently? What would you change?
  • What’s an area of your work you want to improve?
  • What aspect of your job you would like more help or coaching?
  • Do you feel you’re getting enough feedback?
  • Is your work meeting your own expectations?
  • How many hours a day do you feel you’re productive? How could we help you be more productive?
  • Is there anything that you think I should know about?
  • We haven’t been achieving this goal, I want to work with you to figure out why.
  • Is there anything you’re currently working on getting better at?
  • Do you prefer to get feedback in writing so you have time to digest it or are you comfortable with less formal verbal feedback?
  • What is the best piece of feedback you’ve gotten from a supervisor or peer?
  • Is there an area/project/skill where you’d like to get more feedback?
  • What would you do differently, if you were me?
  • What’s one thing that you think I don’t want to hear but that would be good for me to hear?
  • What is the best feedback that you’ve gotten in the last 90 days?
  • What’s one thing you think you should do more of?
  • What type of feedback is most valuable to you?
  • What type of feedback are you missing?
  • Do you feel like you’re on the same page with the team? How often do you think you need meetings to ensure you stay that way?
  • Are there any meetings or discussions you feel you should be a part of that you’re not? Are you included in any you don’t want to be a part of?
  • Who would you like to work more often with? Why?
  • Is everyone pulling their weight on the team?
  • Is there anyone you think you should be working more closely with but aren’t?
  • Who is doing a great job on the team? What have they done?
  • Who on the team impresses you? Why?
  • Who on our team deserves a shoutout for their work and why?
  • Who on the team do you have the most difficulty working with? Why?
  • Who would you like to work more/less often with? Why?
  • What do you like most about working on our team?
  • Do you have any questions about what other team members are working on?
  • Do you help other members on the team?
  • Do others help you when you need it?
  • Are you uncomfortable giving any of your peers’ constructive criticism? If so, why?
  • What’s an inexpensive thing we could do to improve our office environment for the team?
  • If you were to build a small team to work with, who would be on it?
  • Who do you have a hard time working with? Why?
  • What makes someone fit for our team?
  • Is there anything you would do to improve how the team collaborates?
  • What would you change about our team?
  • How could we change our team meetings to be more effective?
  • How would you describe the personality of the team? What sort of person would be a good fit here? What sort of person would add something we’re currently missing?
  • How would you describe the division of work among team members?
  • Is there anything you’d like to see change about the team, and if so, why?
  • Do you think our team activities are inclusive? What can we do to make them more inclusive?
  • If you were in my shoes, what would you change with the team?
  • Is there anything we can do to improve team dynamics?
  • What is a difficult but useful conversation that you think could be had in our team that we are not having?
  • Is there anything that would be productive for me to re-explain to our team?
  • Do you have any questions about the organization?
  • Have you noticed anything at the company that felt off lately?
  • What’s the biggest opportunity that we’re not thinking about?
  • How can the team operate better together? Where are we failing? Where are we succeeding?
  • What’s your least favorite thing about the product?
  • How are you feeling about the company’s future? Why do you say that?
  • If you were the CEO, what changes would you make?
  • What is the company not doing today that we should do to better compete in the market?
  • What’s the biggest opportunity we’re not pursuing?
  • What’s one thing we’d be crazy not to do in the next quarter to improve our product?
  • Do you think our company is taking care of its employees? Why or why not?
  • Are there any aspects of our culture you wish you could change?
  • What are your favorite parts of our culture?
  • What is the number one problem at our company? Why?
  • How could we be more creative or innovative as a company?
  • How well do you feel like you relate to your coworkers? Do you view them as friends, acquaintances, or strangers?
  • What don’t you like about our product or services?
  • What’s the best thing about working here?

To build the rapport and get to know more about them

  • How are you? How is life outside of work?
  • What do you love to do outside of work?
  • What do you like to do in your free time? What are your hobbies?
  • What did you do last weekend?
  • What’s your favorite thing about work?
  • What’s one thing we could change about work for you that would improve your personal life?
  • If around a holiday: Do you celebrate Holiday? How was it?
  • How are your family members doing?
  • How are your parents/grandparents? Where do they live? Do you visit them?
  • If they have children: How is name of child doing? (Ask something related to their age like starting school, playing sports, or other interests.)
  • Do you have any exciting plans for summer/holidays/new year?
  • What did you do for fun in the past that you haven’t had as much time for lately?
  • What drives you? What motivates you to come to work each day?
  • As a kid, what did you want to be when you grew up?
  • How are you feeling about the recent news? Why do you say that?
  • What concerns do you have about the change? What should we do to address them?
  • What’s going well and not so well with the new situation/development?
  • What are your understandings of the new goals and expectations?
  • How is the new situation/development affecting your work? What could be getting in the way of your being effective?
  • Could you tell me a little more about that?
  • Can you share some of the details around that particular issue? (Who was involved? Where? When? For how long?)
  • What do you think caused that to happen?
  • What did you like least about that?
  • How did that affect you?
  • How did that make you feel?
  • If you could change what happened, how would you alter it?
  • What are your impressions of our 1-on-1s? What could we do differently or better?
  • I’m trying to make my 1-on-1s better and would appreciate your honest feedback on this one — what did you like about it, and what could be improved?
  • What are your honest impressions of this meeting?
  • What do you like about our one-on-one meetings? What can be improved?

References