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One-on-Ones: Essential Questions for every Manager
One-on-Ones: Essential Questions for every Manager

Have your One-on-Ones become nothing more than ho-hum status updates? 🥱 We've got some questions that will breathe life back into them.🔥

Stephen Franklin avatar
Written by Stephen Franklin
Updated over a week ago

Want to level up the value of your One-on-Ones? It's as simple as 1-2-3:

  1. Choose the relevant topics you would like to explore with each team member. (Use the suggested frequency guidance to help)

  2. Add the topics to your upcoming One-on-One agendas.

  3. Use the questions to uncover new insights that guide your coaching. Don't forget to record these insights for future reference!

🔥 Pro Tip: Teaming's One-on-One meetings have all these questions and more built right into the experience making it super easy to create your agenda and run your One-on-One in one convenient place.

🤗 Don't forget to include an Icebreaker to lighten the mood and get the conversation flowing.


Well, maybe Icebreakers aren't essential questions but they're a great way to lighten the mood and get the conversation rolling.

  • What’s a food you’ve tried lately that you really liked?

  • If you could erase from your brain one piece of knowledge (memory, fact/set of facts), what would it be?

  • If you could travel anywhere tomorrow, where would you go?

  • What topic do you wish was a college major, but isn’t?

  • If you could be part of any world record, what would it be?

  • Tell me one lie and one truth about yourself. Let me guess which is which.

  • If you were alive in [time period X], what do you think your line of work would have been, or how would you have earned a living?

  • What’s your most vivid memory of a historical event that occurred during your childhood?

  • What was your favorite activity as a 10-year-old?

  • When were you sure a bad outcome would be your ruin, but it turned out to be a benefit?

  • Have you ever had an internet friend or pen pal?

  • What is your favorite compliment of all the compliments you’ve ever received?

  • What are you looking forward to right now?

  • What famous masterpiece painting or sculpture would you like to own?

  • If you went into the witness protection plan, what identity would you like to assume?

  • What is a boring fact about yourself?

  • Which book did you read in college or high school that was actually interesting enough that you still think or talk about it sometimes?

  • If you could rename yourself, what name would you choose, and why?

  • If you could sing like any famous singer in the world (living or deceased), who would it be?

  • Describe something that’s made you smile today.

  • What was your first live concert?

  • What's something new you've learned about yourself in the last three months?

  • What’s something that’s pleasantly surprised you recently?

  • In a single word, describe yourself as a teenager.

  • If you didn’t have to sleep, how would you spend the extra 8 hours?

  • If you weren’t doing your current job, what would your dream job be?

  • Have you ever quit doing something that you used to be really passionate about? Do you regret it? Or are you happy you quit? Do you think you’ll ever take it up again?

  • What question do you wish people would ask you?

  • Of the places you’ve lived or spent significant time, which one had the most pleasing view out the front door/main window/etc. for you? Why?

  • Who is your pick for the most underrated character in a movie or TV show?

  • Describe a time when you changed your mind.

  • If you could live in the setting of any book or movie, without being involved in the story, which would you choose?

  • What’s something about yourself no one would know from looking at you?

  • What is your secret skill?

  • What’s something you love doing that you’re terrible at? Conversely, what’s something you despise doing that you’re great at?

  • How did you get your name?

  • What’s a fun thing you’ve done that you’ll never do again?

  • If you had unlimited resources, what frivolous thing would you collect? Not books. It has to be frivolous.

Career Growth and Development

Member / Role Alignment

(Semiannually or after significant role change)

Make sure team members are a good fit for their role on the team. Help them discover how their traits (strengths, blindspots, interests, ambitions, experience, skills, etc.) will enable them to meet the expectations of their role. Coach them on ways to take advantage and help them to develop a growth plan to address any areas of need.

  • What are your favorite and least favorite parts of this job?

  • What do you wish you could do less often?

  • What do you wish you could do more often?

  • What is going well in your role?

  • What is not going well in your role?

  • What are the necessary skills needed in your role? How are you performing on and growing these skills?

  • Which of your strengths are under-utilized in your current role?

  • When was the last time you felt “flow” or “in the zone” fully using your strengths and losing yourself in your work?

  • What excites you the most about your day-to-day responsibilities?

  • What are your current career priorities and goals that most excite you?

  • Are the responsibilities of your role what you expected? Why/why not?

  • How do you think this job aligns with your personal values?

  • What makes you proud of the work you do?

  • How does this job align with your future career goals?

  • What ideas do you have about how we can match your talent to responsibilities?

  • What other areas of the team or the company could benefit from your strengths? How?

Professional Development


Ensure that you are providing team members with the best opportunities to grow and develop in their professional careers.

  • Which of your skills would you like to develop further with coaching or training?

  • What do you want to learn about or experience but haven’t yet had the opportunity to do so?

  • What new skills would you like to develop?

  • Are you interested in any professional development that would go beyond the role you’re currently in or take you on a different path?

  • What obstacles are standing in the way of your development?

  • What types of professional development opportunities do you find most valuable: classroom setting, on-the-job training, hands-on experience, workshops and conferences, online learning, mentoring, etc.

  • What are you doing to improve your skills and expertise?

  • What are your education goals? What programs could help you further your education?

  • What training do we offer internally that could help you in your development?

  • After doing some research, what are five conferences, training, or other educational opportunities that interest you?

  • What local groups interest you for networking or skill development?

  • What qualities do you look for in a mentor?

  • Is there anyone in our organization you’d like as a mentor?

  • How would you want to benefit from a mentor?

  • What are you learning from your mentor?

  • What professional development goals can we set for you?

  • How have you improved on your development goals since our last meeting?

  • How have you been encouraged in the past to pursue your professional development?

  • What can you start/stop/keep doing to help you reach your development goals?

  • What was your last professional development experience? What did you learn? Was it worth the expense?

  • What could you teach others from your last professional development experience?

  • How will you use what you learned during your last professional development experience moving forward in your job?

Career Advancement

(Semiannually to Yearly)

Empower your team to reach their career aspirations. Help them to develop their personal vision for their career and formulate a plan for how they will realize it.

  • Where do you see yourself in two years? Five years? Ten years?

  • Look across the organization. What role do you want in two years? Five years? Ten years?

  • In the past six months, what have you done to move toward your ideal role/career?

  • In the next six months, what could you do to move toward your ideal role/career?

  • What role/career would let you use your strengths every day?

  • What are your biggest dreams?

  • What do you want your next position in this company to be?

  • What opportunities for advancement are you interested in?

  • What additional responsibilities would you like?

  • Are you interested in leading others?

  • What more are you wanting in your career right now?

  • What other areas of the company do you want to learn about?

  • Are there other roles in the company that you want to learn about?

  • How do your long-term goals align with your career advancement goals?

  • What skills are you developing to meet your career advancement goals?

  • What are you doing to achieve your career advancement goals?

  • What obstacles are preventing you from achieving your advancement goals?

  • How can we help develop your career further?

Job Fulfillment and Satisfaction


(Quarterly to Semiannually)

Discover the best ways to motivate and reward each team member so that they feel valued and appreciated for the impact they are making.

  • What makes you feel valued at work? Undervalued?

  • Overall, do you feel recognized for your contributions?

  • How are you being praised in the workplace? What praise have you received recently?

  • How do you like to be recognized?

  • Which is more important to you as a form of recognition: additional responsibilities, more time off, cash, or job title?

  • Do you prefer public or private recognition?

  • What type of work or accomplishments do you most want to be recognized?

  • Which recognition or rewards are most exciting or impactful to you? (i.e. Hand-written thank you note, Starbucks drink, snacks, a nice gift, time-off, gift cards, a free massage, plane tickets, cash, etc.)

  • Whose recognition means the most to you?

  • What projects or contributions have you not received recognition for that you

    thought you should have?

  • Who have you recognized recently? For what?

  • How do you make your coworkers feel appreciated?

  • What can be done to improve recognition in our workplace?

Benefits & Compensation

(Semiannually or after changes in compensation package)

Periodically review each team member's complete compensation package with them and check to make sure that their current and future expectations aren't diverging from what is feasible or realistic.

  • How do you feel about your current compensation (salaries/benefits/bonuses/etc.)

  • What compensation goals do you have for yourself in the next five years? Ten years?

  • Do you understand your opportunity for bonuses?

  • What questions do you have about the bonuses available?

  • What questions do you have about how compensation is addressed in our organization?

  • Do you understand the benefits we have available?

  • What questions do you have about the benefits you are currently receiving?

  • How could the organization help you better utilize our benefits?

  • What other benefits would you be interested in us adding to our benefits package?


(Quarterly or as needed based on indicators)

Reduce unexpected turnover by identifying early warning signs, before it becomes too late to correct.

  • What makes you happy with your job?

  • What makes you happy with this organization?

  • What attracted you to this job?

  • What attracted you to this organization?

  • What makes you stay in this job?

  • What makes you stay at this organization?

  • What would make you stay in this job and organization over the next two years? Five years? Ten years?

  • What things about this organization, presently or in the future, would lead you to see yourself somewhere else?

  • When you see people leave our organization, why do you think they leave?

Personal Goals and Alignment

Near-Term Goals


Help team members identify and achieve the immediate milestones necessary to accomplish their long-term objectives and support the team's needs.

  • What were the highlights of your past month/quarter?

  • What did not go well last month/quarter?

  • What accomplishment are you most proud of so far this year/quarter?

  • What are your goals for the upcoming month/quarter?

  • How are you tracking your progress on your goals?

  • What kind of support do you need to achieve your goals?

  • Are there any goals that will be challenging for you to accomplish this month/quarter?

  • What obstacles are in the way of you achieving your goals this month/quarter?

  • What work on your plate is most in line with your short-term goals?

  • What work distracts you from your short-term goals?

  • What can you start/stop/keep doing to reach your goals?

  • What circumstances helped or hindered you in meeting your goals this month/quarter?

Long-Term Goals

(Semiannually to Yearly)

Help team members identify and understand their next major objectives on the journey to their future vision. Use this knowledge to provide the support structure that will enable them to achieve these objectives.

  • What are your goals for the next year?

  • What do you see yourself doing in two years? Five years? Ten years?

  • How often do you think about your long-term goals?

  • What inspired these goals?

  • What does your role, our team, and our organization look like when we’re accomplishing these long-term goals?

  • Do you feel your long-term goals are attainable and realistic?

  • How will you measure or track your progress on these goals?

  • What steps will you take to attain these goals?

  • What work is most in line with your long-term goals?

  • What professional development opportunities are most in line with your long-term goals?

  • What goals will be challenging for you to accomplish?

  • What obstacles stand in the way of accomplishing your long-term goals?

  • Who here do you lean on to help set long-term goals?

  • Who outside of this workplace do you rely on to help set goals for the future?

Alignment with Organization & Team Goals, Mission & Values

(Quarterly to Semiannually)

Problems can arise when a team member's personal values and goals are greatly misaligned or in conflict with the goals, mission, or values of the team or organization. Take time to examine whether their values and objectives can coexist with those of the team and organization. Don't expect or require perfect alignment but be on the lookout for incompatibilities.

  • Do you understand how your personal goals align with team goals?

  • How do you see your goals and our team goals aligning with the organization’s mission?

  • What do you think our organization’s most important goals are?

  • Are you able to state what our (organization’s | team's) mission and values are?

  • What questions do you have about the (organization’s | team's) mission or values?

  • How does your job benefit or connect to our overall (organization’s | team's) mission?

  • How do you demonstrate (organization's | team's) values at work on a daily basis?

  • How do your personal values align with our (organization's | team's) values?

  • Do any of your personal values conflict with our (organization's / team's) values?

  • Are there (organization | team) values that resonate better or worse with you?

  • How could our (organization | team) better live our mission or values?

  • In what ways could we improve our (organization's | team's) mission and value statements?

Job Performance

Progress Check

(As needed based on indicators)

Try to avoid using One-on-Ones as your way of getting progress or status updates 🙅 but when you sense a team member might be struggling, examining their recent work activities alongside them can be an effective way to better understand their challenges and identify opportunities for improvement for you to coach them on.

  • How are your projects or tasks going?

  • How do the projects or tasks you are working on align with your goals?

  • Do you have clarity regarding your responsibilities?

  • How are you prioritizing your projects or tasks?

  • How will you, the team, and the company

  • benefit from this project or task?

  • How will you evaluate the success of this project or your work?

  • What do you want to learn from this project? What have you learned so far?

  • What is keeping you from accomplishing your work? What are the roadblocks or bottlenecks?

  • What could keep you from completing your projects or tasks on time?

  • How will you ensure your projects and tasks are completed on time?

  • What would help you complete your projects or tasks? (e.g. additional resources, coaching, assistance, etc.)

  • Was the project a success?

  • Did you complete your work successfully?

  • What went well? What could have gone better?

  • What could we change in the future to improve these types of projects or tasks?

  • What other projects or tasks would you like to work on?

  • How can you contribute to other projects or tasks for which our team is responsible?

  • How do you think you've done on the three key areas we discussed in your last progress check?

  • What do you think will be the keys to your success over the next four months?

  • What worries or concerns do you have about your ability to be successful in the coming months?

Tools, Resources & Environment


Enabling your team to succeed is a critical responsibility for any manager. Periodically check in with team members to ensure they have the tools, resources, and work environment they need to succeed.

  • Do you have the resources and tools you need to perform your job?

  • What resources and tools help you the most?

  • Which resources and tools do you use most often?

  • Are there tools your colleagues use that you don’t know how to use or have access to?

  • What resources and tools could help you perform your job better?

  • Are there any resources or tools that you find useless?

  • Do you have all the information needed to do your job effectively?

  • What technology could improve your workspace?

  • Is your workspace comfortable and supportive of your health?

  • What is your preferred work environment? (i.e. open common areas, cubes, enclosed office, etc.)

  • Do you prefer different work environments for different types of work? Explain.

  • What could be improved in your work environment to help you produce high-quality work more efficiently?

Process & Workflow

(Quarterly or as needed based on indicators)

Examining how team members approach their work provides a natural opportunity for coaching and is also an effective strategy for identifying team-wide inefficiencies and other improvement opportunities.

  • How are you accomplishing this project or task? (i.e. timing, tools/resources, process/steps, etc.)

  • Do you have the information you need to complete your tasks?

  • What activities take up the most time of your day or week?

  • What distractions or interruptions keep you from getting your work done?

  • What mental thoughts or roadblocks get in the way of your success?

  • What part of your working routine keeps you the most productive? Least?

  • What part of the day/week do you have the most energy and focus?

  • What aspects of your work environment help you focus?

  • What type of work takes the most focus and energy?

  • What are the biggest time wasters for you each week?

  • What causes you to lose focus or energy?

  • What do you do when you feel unfocused or unmotivated? What could help you bounce back quicker?

  • In an ideal, productive day at work for you, what tasks could you accomplish?

  • Which coworkers do you admire for their productivity and efficiency? What behaviors do you notice in their work styles?

  • What changes can you make to become more productive at work?

  • What tools could help your productivity?

  • How can your schedule be changed to help your productivity?

  • How can your work environment be changed to help your productivity?

  • How can I help you become more efficient?

  • How can I help you become more effective in your role?

Managing Workload

(Monthly or as needed based on indicators)

Keep a pulse on how each team member is experiencing their workload and the effects it's having on them. Understanding their "reality", not yours, helps you to know when action is needed and how to best help them when it is.

  • How are you doing? Are you feeling stressed?

  • Do you feel the time you are allotted per task is too little, too much, or just right?

  • Is the work you’re doing interesting?

  • Do you feel challenged by your responsibilities?

  • What work is too demanding or causing burnout?

  • Do you feel balance in the types of tasks you are doing?

  • Do you feel over-worked, under-worked, or just right?

  • Are you ready to take on new responsibilities?

  • How can I help alleviate your workload?

  • What work could be shifted off your plate?

  • What work could we delegate to someone else, so you can take on new, more challenging responsibilities?

Managing Change

(After significant change at organization, team, or individual levels)

Individuals react to change differently. When changes occur, it's important to spend time with team members to understand how the changes are impacting them and then coaching them on ways they can successfully adapt to the new situation or environment.

  • Why do you think we’re making this change?

  • How will this change impact your role and our team?

  • How do you think we’ll benefit from this change?

  • What will be difficult about this change?

  • How could we better communicate changes that happen in our organization?

  • How can we make this change a smooth transition for you and our team?

  • What skills or information do you have that could help us navigate through the transition?

  • As we make this change, what are we forgetting? What do we need to address first?

  • What other changes do you think would benefit the organization or the team?

Performance & Behavioral Improvement

(Quarterly or as needed based on indicators)

Don't allow performance or behavioral issues to cause irreversible damage to the team. Proactively identify, understand, and address these issues early so that you can coach team members and get them back on track. Even when issues aren't obvious, spend some time with team members probing for hidden issues that may be bubbling under the surface.

  • How did you perform on your goals?

  • How do you think you could improve as an employee?

  • How can I help keep you accountable for achieving goals and results?

  • How will you keep yourself accountable for meeting goals, deadlines, and results?

  • How are you being efficient/ inefficient with your time?

  • What actions can be taken to help improve your performance in the future?

  • What steps have you taken to improve your performance?

  • How have you seen your performance improve?

  • What areas of performance are in need of improvement?

  • How can we take action? (Include specific and measurable objectives that are relevant and time-bound; include meeting dates and a final review of outcomes and measured improvements.)

  • Discuss current satisfaction in your current performance and areas you would like to improve.

  • What specific training and/ or professional development do you feel would enhance your job performance and job satisfaction?

  • What is a recent situation you wish you had handled differently? What would you have changed?

  • What behaviors do you bring to your work and to the team that have a positive impact?

  • What are other situations you can use these strengths?

  • What behaviors do you need to improve or continue to grow?

  • How will you practice improving these behaviors?

  • How would you advise someone else who is working on these behaviors?

Team & Organizational Culture

Organizational Culture


Stay on top of the team's perceptions of the organization's culture and get feedback on potential shortcomings and improvement opportunities.

  • How do you feel about our organization's culture?

  • How can we improve our organization's culture?

  • What other organizations do you admire for their culture?

  • How can we be more like these organizations?

  • What is your favorite thing about our organization's culture?

  • What is your least favorite thing about our organization's culture?

  • How is our organization loyal to its employees?

  • What makes you proud to say you work here?

  • What is fun/not fun about working here?

  • What do you most enjoy about working here? What do you not enjoy about working here?

  • How can we compete in the market better, in your opinion?

  • What are our obvious shortcomings? If you could change one thing about our organization, what would it be?

  • How could we be more creative or innovative as an organization?

  • Can you provide one suggestion to help improve one of our products or services?

  • What are the primary risks or issues with our products or services that we should work to resolve?

  • If you lead this organization, what would you do differently?

Team Culture


Keep a close watch on how team members perceive the team's culture. Use this feedback to help you and the team find ways to improve.

  • How do you feel about our team's culture?

  • How can we improve our team's culture?

  • What other teams do you admire for their culture?

  • How can we be more like these teams?

  • What is your favorite thing about our team's culture? Least favorite?

  • What makes you proud to say you work on this team?

  • What is fun/not fun about working on this team?

  • What do you most enjoy about working on this team? Least enjoy?

  • What are our obvious shortcomings? If you could change one thing about our team, what would it be?

  • How could we be more creative or innovative as a team?

  • If you lead this team, what would you do differently?

Corporate Social Responsibility


If your organization has a Corporate Social Responsibility program, investigate whether these programs are understood and if they align with the expectations of the team. If no CSR program exists, investigate whether or not this is an expectation or desire for team members and if it might be a source of discontent.

  • What causes are most important to you?

  • What do you believe our company’s social responsibility is to the community, both locally and globally?

  • Are you aware of the CSR programs available to you?

  • What questions do you have about our CSR programs?

  • What opportunities do you or our team have to contribute to our CSR initiatives?

  • What are the goals of our CSR initiatives? What results do you see?

  • How could we better broadcast the CSR programs we have available within the company?

  • How could we better position our CSR programs internally and externally?

Workplace Relationships

Team Camaraderie


Creating a trusting, cohesive team is key to enabling the teamwork needed to unlock its full potential. Frequently investigate how each team member perceives the team's overall health and how they personally view their place or "fit" within this team.

  • Do you feel connected or disconnected from the team? In what way?

  • Do you feel our team is close-knit? Why or why not?

  • What would help create stronger bonds between our teammates?

  • Do you feel our team trusts each other? Why or why not?

  • Do you feel safe expressing your thoughts and opinions on this team? Why or why not?

  • Do you feel you can be your "true self" on this team? Why or why not?

  • Who has helped you succeed in your responsibilities? How?

  • Who have you helped succeed with their work? How?

  • What is your definition of teamwork?

  • How is teamwork encouraged in our team?

  • How can we improve our level of teamwork?

  • What kind of team-building activities would you like to see in the workplace?

Peer Relationships

(Semimonthly to Monthly)

The direct relationships between team members have a powerful impact on each member's experience on the team. Spend some time checking in on these relationships and look for opportunities to encourage stronger bonds and head off any unproductive conflict before it becomes a larger issue.

  • Which of your teammates do you depend on and trust the most? Why?

  • What constructive feedback have your peers given you?

  • How can you increase trust with your teammates?

  • How can I help you build trust with your teammates?

  • What do you expect from your teammates?

  • How can your teammates count on you?

  • What can you do to improve your relationships with your teammates?

  • What do you admire in your team members?

Manager Relationship & Expectations

(Semimonthly to Monthly)

The relationship with their manager can be the most influential and impactful relationship (both positively and negatively) for any team member. Take time with every team member asking for and listening to feedback on your relationship and your performance. Use these gifts to help you improve and become the manager you know you can be.

  • Who are some leaders you admire? Why do you admire them?

  • What type of leadership style do you prefer?

  • What type of leadership style resonates negatively with you?

  • What kind of support do you expect from a manager?

  • Do you want more or less direction from me on your work? Why?

  • What can I do to help you be more effective and engaged?

  • What do you like/dislike about my management style?

  • How can I improve as your manager?

  • What do you want to know about me?

  • How am I setting you up for success?

  • If you were me, what would you do differently?

  • How can I help you manage your direct reports better?

  • What areas are you struggling with in managing your team?

  • What ideas do you have on growing as a manager?

Team Member Well-being

Finding Balance

(Quarterly to Semiannually)

The dynamics of the modern work environment make it challenging to maintain balance in our lives. Periodically investigate how team members are navigating these challenges so that you can provide guidance and take corrective action to help members that are struggling.

  • How do you feel about your work-life balance right now?

  • How could you maintain balance between your work and personal life?

  • How can I make your work-life balance better?

  • What parts of your job negatively affect your personal life?

  • What parts of your personal life negatively affect your work performance?

  • How does your time management affect your progress at work? At home?

  • How often are you able to satisfy both your job and personal responsibilities?

Mental and Emotional Well-being Checkup

  • Coming soon. (Let us know if this is an area that you would like guidance)

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