The Big List of 300+ One on One Meeting Questions

Are you making the most of your one-on-ones? Use this list of 300+ questions for managers like you to ask in your next meeting!

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One on one meeting questions

Ask these questions during your 1:1 to kick things off

If you listen to music while working, what kind of music is it?
What superpower would allow you to complete your work ten times faster?
If you had to work full-time for a month while located in the last place you vacationed, could you do it?
If you could only talk to one person for a whole week, and it had to be one of your colleagues, who would it be?
What are some songs or albums that you know all the words to?
If you could be any non-human animal, which would it be and why?
What celebrity or historical figure do you admire? Why?
Would you rather live in the mountains or on the beach? Why?
What's an accomplishment you're proud of?
Where is the farthest place from your currently location that you've ever been?
What's something people are often surprised to learn about you?
What's your favority book or film, and why is it your favorite?
What's something that's on your bucket list?
Would you rather travel to Mars or to the unexplored depths of the ocean? Why?
If you were to give your younger self some advice, what would it be?
What is one belief that you've had your whole life that you think has helped you become who you are today?
How are things with your family?
What did you get up to this weekend?
Who is the best manager you ever had? What did you like about them?
What makes 1:1s the most valuable for you?
Why did you decide to work here?
What made you decide to become a(n) [position they're in]?
What's your favorite part about living in [your city/town/region]?
Where did you grow up / go to college?
Who do you really admire? Why?
Can you recommend any good podcasts or books?
What vacation (or staycation) plans do you have coming up?
What’s on your mind?
As a kid, what did you want to be when you grew up?
If you had millions of dollars, what would you do every day?
How was your weekend?

Ask these questions during your 1:1 to stay aligned on projects and set expectations

Using a percentage, how full is your plate right now?
How are changes you've implemented affecting the overall strategy of your current project?
What work are you doing that wasn't planned? How does this affect your workload?
What is working as expected? What is not?
What concerns do you have about this project?
How do you know you've had a productive day?
How do you plan out your week?
How do you like to organize your day?
What percentage of your time do you spend in meetings vs. doing deep work?
What do you think are the key skills for your role? How would you rate yourself for each of them?
What behaviors do you bring to your work and the team that have a positive impact?
What is a recent situation you wish you'd handled differently?
What specific training do you feel would enhance your job performance and satisfaction?
How have you seen your performance improve?
What steps have you taken to improve your performance?
How can I help keep you accountable for achieving goals and results?
How can your schedule be changed to help your productivity?
In an idea, productive day at work for you, what tasks could you accomplish?
What could help you bounce back quicker?
What are the biggest time wasters for you each week?
What type of work takes the most focus and energy?
What part of the day or week do you have the most energy and focus?
What part of your working routine keeps you unproductive?
What part of your working routine keeps you productive?
What distractions or interruptions keep you from getting your work done?
What activities take the most time out of your day or week?
What worries or concerns do you have about your ability?
What do you think will be the keys to your success over the next few months?
What other projects or tasks would you like to work on?
What could we change in the future to improve these types of projects or tasks?
What could keep you from completing your tasks on time?
What do you want to learn from this project?
How will you evaluate the success of this project or your work?
How are you prioritizing your projects or tasks?
Do you have enough clarity about your role and responsibilities?
What are you committing to between now and the next time we meet?
Do you have any questions about the recent change involving X?
What are your plans and priorities this week?
Last time we spoke you said X was a challenge for you; how is that going?
What can I hold you accountable for next time we talk?
What’s your outlook on next week?
Reflecting on last week, what could have been done better?
Are there any obstacles I can remove for you?

Ask these questions during your 1:1 to keep track of your career progress

If you could spend one workday a week doing whatever you wanted, what would it be?
Have any of your goals changed since the last time we talked about them?
What work are you doing here that is most in line with your long term goals?
What are three long term professional goals that you have? Why are these important to you?
What are some habits you'd like to get rid of?
What are some habits you'd like to develop?
What would you like to achieve by the end of the year?
What other areas of the company do you want to learn about?
Are you interested in leading others?
What do you want your next position in this company to be?
What are your biggest professional dreams?
Where do you see yourself in two, five, or ten years?
What could you teach others from your last professional development experience?
What qualities do you look for in a mentor?
What local groups interest you for networking or skill development?
What are your education goals?
What types of professionaly development opportunities do you find most valuable?
Is there someone at the company you'd like to learn from?
What are two or three new skills you'd like to learn on the job?
How are you/your team progressing towards established goals?
What's one thing (or a few) you learned this week?
Do you feel we’re helping you advance your career at a pace you would like?
What’s something you’re itching to try that you haven’t had the time or resources to do?
Is your current role helping you grow in your career at the pace you want?
What efforts would you like to be most recognized for?
What about this goal is important to you and what will be different when you achieve the goal?
What aspect of your job you would like more help or coaching?

Ask these questions during your 1:1 to check up on personal life and wellbeing

How long is your daily commute?
Do you feel like you have to prioritize your job over your personal life?
How many hours do you sleep on an average work night?
Do you check your emails after you leave the office?
How often do you work on vacation?
How often do you work on the weekend?
How often do you take work home?
Have you ever missed a personal event because of work?
How often do you work overtime?
Do you have time to get the rest you need?
What's something you do to relieve stress?
What's something that brought you joy this month?
What are some personal goals this year?
What drives you? What motivates you to come to work each day?
What did you do for fun in the past that you haven't had as much time for lately?
What do you like to do in your free time? What are your hobbies?
What's one thing we could change about work for you that would improve your personal life?
What adjustments can we make that would improve your well-being?
What was one of your funniest moments at work?
How are you planning to balance work and personal life this year?

Ask these questions during your 1:1 to understand team and company culture

If you could invent an app that would help our organization in any way you want, what would your app do?
Have you been disappointed with a decision made by the company in the past year?
How can we make our company more inclusive and diverse?
What do you think is the biggest risk for our company?
What would you change about our product?
What are other teams not doing that you wish they would do?
What are other teams working on that seems unimportant or counterproductive?
How do you feel about the priorities of the teams you're dependent on?
What do you think about the relationship between our team and other teams at the company?
What's it like to work with other parts of the company?
How have you been getting along with other teams within our department?
Do you think we all work well together? What can we do to make us more synergistic?
What is a difficult but useful conversation that you think could be had in our team that we are not having?
What's something we can/should start doing as a team?
Do you think our team activities are inclusive? How can we make them more inclusive?
What is a team building activity that we could do?
Is there anything we can do to improve team dynamics?
Are there people on the team that you think you could get along better with?
Do you think we're headed in the right direction as a team?
Are you uncomfortable giving any of your peers constructive criticism? If so, why?
Do you help other members of the team? Do others help you when you need it?
Who is kicking ass on the team? What have they done?
Is everyone pulling their weight on the team?
Are there any discussions you feel you should be a part of that you're not?
Do you feel like you're on the same page with the team? How often do you think you need meetings to ensure it stays that way?
What would convince you to leave for a job somewhere else?
How could we change our team meetings to be more effective?
How well do you feel you relate to your coworkers?
How could we be more creative or innovative as a company?
Which company values do you like the most? The least? Why?
What are your favorite parts about our culture?
Are there any aspects of our culture you wish you could change?
Do you think our company is loyal to our employees? Why or why not?
If you were CEO, what's the first thing you'd change?
What's one thing we'd be "crazy" not to do in the next quarter to improve our product?
What is the company not doing today that we should do to better compete in the market?
Do you feel that important conversations happen publicly?
How well-informed do you feel about what's going on in the rest of the organization?
How do you feel about the amount of communication in our team and organization?
Have you had any interactions with people you work with you'd like to discuss?
How aligned do you feel with where the company is going?
How confident do you feel with where the company is going?
Who on the team do you have the most difficulty working with? Why?
What, according to you, is our company's biggest problem?
How do you think your role contributes to the company's success?
Who would you like to work more often with? Why?

Ask these questions during your 1:1 to make sure reports enjoy their current role

Do you think leadership upholds policies fairly for all employees?
Do you think the organization has fair policies for all employees?
Do you feel you are treated fairly compared to your peers?
Is the feedback you receive about your performance constructive?
Do you feel like leadership respects your personal family time?
Do you think you have had enough training to solve the issues you encounter?
Do you think your job makes a positive difference in others' lives?
Do you think you go beyond your limits to fulfill a task?
Do you feel included in decision-making?
Do you feel that your opinions are heard and valued by senior staff?
If something unusual comes up, do you know who to go to for a solution?
Do you struggle to get the information you need to make good decisions at work?
Does your team provide you support whenever needed?
Is your team an inspiration for you to do your best at work?
Will you still be working here at this organization in 2 years?
Do you believe there is an opportunity for individual career growth and development within the company?
Are the strategic objectives of the organization clearly communicated?
What would need to happen in the next week to give you great satisfaction?
What are the things you've done at this company that you're proudest of?
Do you feel that your work is appreciated?
Who are you friends with at work?
What work could we delegate so you can take on new, more challenging responsibilities?
What work could be shifted off your plate?
Are you ready to take on new responsibilities?
Do you feel overworked, underworked, or just right?
Is the work you're doing interesting?
Do you feel the time you are allotted per task is too little, too much, or just right?
Are you feeling stressed or burned out?
What other areas of the team or company would benefit from your strengths? How?
How can we match your talent to your responsibilities?
What makes you proud of the work you do?
How does this job align with your personal values?
Are the responsibilities of your role what you expected? Why or why not?
When was the last time you felt like you were fully using your strengths at work?
Which of your strengths are under-utilized in your current role?
What is your least favorite part of this job?
What is your favorite part of this job?
What has energized you in your role [over a period of time]?
On a scale of 1-10, how happy are you at work?
How do you feel about your current workload?
Do you have any worries related to your work, role or company? How can I help?
What do you feel is your greatest accomplishment here?

Ask these questions during your 1:1 to check how you're doing as manager

What were the top takeaways of this meeting? What are our next steps?
Was this meeting helpful?
What was the most useful part of our conversation today?
What is the most valuable part of a meeting for you?
Are there any meetings that could be shorter or cut altogether?
Could our team meetings be more productive?
Are our 1-on-1 meetings a good use of your time?
What type of feedback are you missing?
What type of feedback is most valuable to you?
Is there an area/project/skill where you'd like to get more feedback?
What's one thing you think you should do more of?
What is the best feedback you've gotten in the last 90 days?
Do you feel like I acknowledge/recognize the positive work that you do?
Do you feel that I represent the team well to the rest of the company? What would you change?
If you were in my shoes, what would you change with the team?
What's one thing that you think I don't want to hear but that would be good for me to hear?
Is there anything I could do to invest more in your growth?
Would you like more or less direction from me?
Is any part of your job unclear or confusing?
When have you felt stressed or overwhelmed in the past month? What can I do to prevent that?
Any surprises since you've joined, good or bad, that I should know about?
How do I know when you're in a bad mood or annoyed?
What's your preferred method of communication?
What frustrates you or makes it much harder for you to learn?
How do you prefer to receive recognition?
What's your favorite thing I do as a manager I should keep doing?
What have your past managers done that you'd like me to also do or not do?
Is there a situation you'd like my help with?
What do you like about my management style? What do you dislike?
What could I do to make you enjoy your work more?
What would you like to know about me?
What aspects of your work would you like more or less direction from me about?
What's an area of your work you want to improve?
Do you feel you're getting enough feedback? Why or why not?
Is there anything we didn't cover that you'd like to discuss next time?
What can I help you with between now and the next time we meet?
What feedback do you have for me?
What could I do as a manager to make your work easier?
If you were managing the team, what would you do differently?
Do your peers share their feedback with you? What constructive feedback did you receive from them?
What can I do to build our team's reputation in the company?
How do you prefer to receive feedback?

Ask these questions during your 1:1 to dig into current limitations

How can we encourage more collaboration between teams and departments with the tools you use most?
Do we provide enough training on our tools and resources?
What are the limitations of the current tools and platforms we use?
Which tools or platforms do you wish we used?
Are you using any free trials/subscriptions our organization doesn't provide to do your job better? If so, which ones?
How could the systems, tools, and resources we use be better leveraged?
Do you feel welcome using the company's community and collaboration tools?
Are all the company's tools and resources accessible for you?
Do you know how to use all the tools and resources available to you?
What could be improved in your environment to produce high-quality work more efficiently?
Is your workspace comfortable and supportive of your health?
What is your preferred work environment?
What technology could improve your workspace?
Are there tools your colleagues use that you don't know how to use or have access to?
Which resources and tools do you use most often?
What resources and tools help you the most?
What resources and tools could help you perform your job better?
Do you have access to all the resources and information you need?
Are there any tools and/or resources that you rarely use and can get rid of it?

Ask these questions during your 1:1 to understand the impact of working remote

When you have a creative idea or epiphany while working from home, what do you do with it?
Do you feel like you could to to anyone asking for help while working remotely?
Do you feel you have opportunities for "water cooler" type discussions with the team to help you spur on ideas?
How well do you feel you know your remote coworkers?
Do you think decision making drags out for too long because of remote work?
Do you think our decision-making process includes those who work remotely well?
Do you feel the company supports remote staff effectively? How could we improve?
What do you do to recharge each day?
What helps you feel connected to others and counteract the potential loneliness of working remotely?
How long have you been working remotely? What were the most challenging and surprising things when you first started?
What's your favorite part about working remotely?
How challenging is it for you to stay focused when working from home?
Do you ever feel lonely or isolated at work?
Have you been able to find clear boundaries between work and personal life?
How has working remotely impacted your family routines?
How has remote work imacted team dynamics - positively and negatively?
What can I or other people in our company do to make remote work easier for you?
How are the new remote work tools we're using working for you?
What do you like and dislike about working from home?
What’s the biggest challenge that you face while working from home?

Ask these questions during your 1:1 to explore other topics

On a scale of 1-10, what is the likelihood of your idea succeeding? What would it take to make it a ten?
What's the worst-case scenario you're worried about?
I like the sound of your idea, but it's still unclear to me. Can you try explaining it again?
What could be your first step in implementing your latest idea?
What do you need to develop your idea further so that it's ready to discuss with the broader team? How can I help?
What are your options for handling your current challenges?
Are there any new ideas you'd like to discuss with me/the team?
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