FlexOS | Best One-on-One Questions for Impactful Conversations

Best one-on-one Questions for Impactful Manager-Employee Conversations

Quickly draft your 1:1s with our one-on-one questions generator to have more meaningful conversations, and build trust, ...

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Meeting Notes

Brian Q
Product Design Director, FlexOS
With 7+ years of experience in innovation and technology, Quang brings a unique perspective to the world of work innovation.
October 22, 2023

Gallup’s research on the world's best managers reveals their fourth habit is holding one meaningful conversation weekly with each team member. Regular one-on-one meetings provide the perfect opportunity for this valuable face-to-face time.

A manager can connect with their team members on a personal level and ask deeper questions in ways team meetings cannot. This helps managers gain a greater understanding of and empathy for their team members as individuals.

Yet Microsoft data indicates less than a third of managers use one-on-ones to provide clear guidance and feedback. Perhaps many fail to take full advantage of their potential. Effective managers make one-on-ones a portal for development, not just status check-ins.

Our comprehensive guide is here to help you conduct more meaningful and impactful one-on-one meetings. It includes question banks and tips on selecting the right questions to ask in different scenarios.

Timely and thoughtful questions unlock each team member's unique strengths and growth areas. Like icebreaker questions, good one-on-one questions build trust, empathy, and good connections with your team. With this foundation, performance is sure to follow!

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1:1 Meeting Question Bank

Questions to break the ice and set the tone

How was your weekend? Do anything fun?
What's your favorite way to spend a day off?
What's something quirky or surprising about you that most people don't know?
What's something that made you laugh recently?
What's the best book you've read or show you've watched recently?
What's your favorite motivational quote?
What's your favorite way to treat yourself when you need a pick-me-up?
What song always puts you in a good mood?
What are you most looking forward to in the coming months?
What's one small thing that made you happy this week?
What food do you crave most often?
What is one personal goal you have for yourself?
What's on your bucket list for this year?
What hobby or activity have you always wanted to try but haven't yet?
What is the best gift you’ve ever received?
What’s your favorite thing about working with me?
What is one thing you felt grateful for this week?
If you didn't have to sleep, what would you do with the extra time?
If you could learn any new skill, what would it be?
If you could time travel, where/when would you go first? Why?
If you won the lottery tomorrow, what would be the first thing you would do?
If you could live anywhere in the world, where would your dream home be?

Questions to build rapport and trust

What do you value most about our working relationship?
Do you feel comfortable voicing concerns, asking questions, or giving me feedback?
How do you prefer to receive coaching and feedback from me?
What motivates you at work?
What makes you feel demotivated or frustrated at work sometimes? How can I help with that?
What makes you feel empowered and engaged at work? How could I encourage more of that?
What expectations do you have for me as your manager?
Where do you feel less confident or need more support? How can I assist?
What is something unique about you that I likely don’t know yet?
What is your favorite thing about working with our team?
What advice do you have for me on how to best support you right now?

Questions to understand the current workload and progress

What projects are you currently working on? How are they going?
What progress have you made this week toward your goals?
What's the biggest priority for you this week?
Do you feel you have the right workload right now? Too much or too little?
Is there any part of your role you want more or less focus on?
What responsibilities or tasks demand the most time/energy from you? How can we optimize this?
Are you facing any obstacles in meeting deadlines? How can I remove those?
How satisfied are you with your productivity and efficiency lately?
What tools or resources would improve your productivity?
How satisfied are you with the balance and prioritization of your work lately?
What support from other teams do you need more of? How can I facilitate that?
How much time do you spend in meetings compared to focused work time?
What else can I do to check in on and monitor your workload and progress?

Questions to align goals and expectations

How would you prioritize your current goals?
Do you have the resources needed to achieve your goals? If not, what is missing?
Are you clear about your scope of work and expectations?
Do you have a clear timeline in mind for achieving these goals?
What strategies or approaches do you plan to use to achieve these goals?
Where is the biggest gap between my expectations and yours? How can we get better aligned?
Should we re-evaluate any team or company goals?
How could we better align your goals with team goals?
Do you ever feel exhausted between competing priorities? How can I help with that?
How satisfied are you with the goals we’ve set together? What could improve that?
What goal are you most excited about accomplishing in the months ahead?

Questions to address challenges and roadblocks

What is your biggest challenge or roadblock at work right now? How can I help remove it?
Do you feel you have the necessary resources and tools to overcome challenges effectively?
What obstacles could hinder your upcoming projects or goals? How can we get ahead of them?
Are you waiting on anything from others to move forward? How can I help speed that up?
Do you feel supported by your colleagues and the team when facing challenges?
Are there any communication gaps that contribute to misunderstandings or inefficiencies? How can we improve communication channels?
When you get stuck, what goes through your mind? How do you get unstuck?
What is your biggest time-waster right now? How can we eliminate it?
Do you feel overloaded with meetings? What meetings or obligations take time away from your core work?
What work feels like "grunt work" to you? Can we automate or delegate it?
What could I do to help you feel less burnt out?
What are you working around that you shouldn't have to? How can I remove those obstacles?

Questions to understand your employee's needs

If you could change one thing about your job to make it better, what would it be?
How could I make your work more fulfilling?
What problems, if solved, would make your job easier?
If I could take any annoyance off your plate, what would it be?
What is at the top of your wish list to help improve your performance?
What data or metrics would help you prioritize and make decisions?
What are your top questions or concerns I can help address?
Do you feel your current workload is manageable? What projects or tasks would you delegate if you had an assistant or intern?
What is one thing we could do to improve your ability to focus and be productive?
Are there any training programs, workshops, or conferences you believe would be beneficial for your professional development?

Questions to check on employees’ well-being and engagement

How are you feeling both personally and professionally?
Are you getting enough rest and recharge time outside of work?
How do you manage stress and maintain your well-being outside of work?
Is there anything outside of work impacting your focus or productivity?
What parts of your job bring you satisfaction and joy day-to-day?
When did you last feel truly excited about your work?
What causes you stress or anxiety at work? How can we alleviate that?
Do you feel your role makes good use of your skills and strengths? If not, what could we change?
When did you last feel disengaged or bored at work? What was the cause?
How connected do you feel to the team values?
What keeps you motivated on low-energy days?
What causes you to lose motivation at work?
When do you have the most focus and energy?
What does high engagement look and feel like for you?
How can I know if your workload is nearing burnout levels?
What are your tricks to stay engaged throughout the workday?
What kind of activities or projects do you find the most energizing and engaging?

Questions to check on your team dynamics and collaboration

How are communication and collaboration between you and your teammates?
Are there any interpersonal issues or conflicts I should know about?
Who would you like to collaborate more with and why?
Do you feel there are clear roles, responsibilities, and ownership on the team?
Who do you most enjoy collaborating with? Why?
Whose work style is most different from yours? How do you bridge that gap?
What does your ideal team culture look like? How close are we to that now?
Are there unnecessary meetings eating into collaborative work time?
What is your preferred method of communication and how can we ensure effective communication within the team?
Are you satisfied with the frequency and quality of team meetings? How could we improve them?
Are we recognizing team achievements regularly enough?
If you could change one thing about the team culture, what would it be?
How do you feel about the level of collaboration within the team? Is there room for improvement?

Questions to understand personal development and growth goals

How can we align your skill development with both your personal aspirations and the team's needs?
Are there any external training programs or workshops you believe could accelerate your growth?
What new skills and knowledge would you like to develop?
How do you envision your role evolving over the next year? What new responsibilities interest you?
What long-term aspirations do you have that we can start building toward?
What part of your job needs more development and coaching?
What new areas or responsibilities would you like to explore or take on?
What career goals could I help you set to stretch your skills and experience?
What projects could I assign to build your capabilities for future roles?
How satisfied are you with opportunities for promotion and advancement here?
What department or team would you choose to shadow or learn more about?
Who inspires you most when it comes to career success? Why?
What new things do you want to learn outside your current role?
If you could trade roles with someone in a different department for a day, whose role would you choose and why?
How can I best support you in setting and achieving these personal development goals?

Questions to offer feedback and coaching

How can I better tailor my feedback and coaching to match your individual learning style and preferences?
Are there specific areas or tasks where you feel more feedback would be beneficial for your growth?
What aspects do you want to ask for my feedback on?
What's the most impactful change you've made based on feedback or coaching received from me?
Do you feel our feedback and coaching sessions are frequent enough to support your continuous growth?
How have my coaching methods been helpful so far? What other approaches could I try?
How do you prefer to receive feedback and coaching from me?
Do you feel comfortable discussing mistakes or failures with me? How can I make you more at ease?
What is a recent situation you learned from? How will it influence your future work or decisions?
What specific feedback from me has been most useful and constructive for you? Why?
Are there times you wanted more feedback from me but did not get it? When specifically?
What feedback delivery methods work best for you - written, verbal, passive, active, etc.?
What recent feedback has been most meaningful in improving your performance? How so?
When something goes wrong, how do you prefer to discuss it with me?

Questions to get feedback to improve your leadership

What feedback do you have for me? Are there aspects of my managerial style that could be improved?
What areas or situations would you like to see me handle differently? Are there any instances where you felt I could have provided better guidance or direction?
Do you feel that I effectively communicate the team's goals, expectations, and priorities? If not, how could I improve?
Am I providing you with enough opportunities for professional growth and development? If not, how could I better support you in this area?
Do you feel comfortable sharing your concerns or challenges with me? Is there anything I can do to create a more open environment for feedback?
Do I strike the right balance between providing guidance and giving you autonomy in your work? If not, how could I improve?
Do you feel that I listen to your ideas and suggestions? Is there anything I can do to encourage more open discussions?
If you were in my position, what's one change you would make to improve the team's overall experience and performance?
How do you think my leadership style impacts team morale and motivation? Is there anything I could do differently to enhance it?
When have I made a decision you disagreed with? How could I have handled that better?
What more can I do to make you feel supported, heard, and valued?
How could I do a better job of explaining my decisions and reasoning to you?
What could I do to make you feel more comfortable approaching me with questions and concerns?

Questions to spark creative thinking

If you could redesign your role from scratch, what would it look like?
Imagine you're a consultant advising us from the outside. What recommendations would you give to improve our processes?
If you had unlimited resources, what kind of project or idea would you pursue right now?
If you could solve any problem in our industry, what would it be and how would you approach it?
What's the most unconventional solution you can think of for the challenge we're currently facing?
What should we stop doing to become more efficient, effective, or innovative?
What trends or technologies outside our industry could we adapt to improve our products/services?
If you were to design a marketing campaign that stands out, what creative elements would you include?
What's a new way we could engage with our customers that we haven't tried before?
If you had to completely reinvent our product/service, what features or elements would you introduce?
What's a feature or aspect of our current offering that you think could be enhanced to surprise our customers?
How could we change our approach to solving a problem if we considered it from the customer's perspective?
What's something you've learned from a different field that you believe could be applied to our work?
What seems impossible but is actually feasible if we change our thinking?
If budget and resources were no concern, what initiatives would you want to implement?

Questions to check on your remote work culture

What challenges are you facing working remotely? How could we improve?
Do you feel connected with your teammates while working remotely?
How often do you interact with your team members and colleagues virtually? Are there communication channels or tools that you find particularly effective or lacking?
What remote collaboration policies or guidelines do you think have been working well for our team? Are there any adjustments you'd recommend?
What strategies or routines have you developed to stay productive and focused while working from home?
How comfortable do you feel reaching out to your team members and colleagues for help or support when working remotely? Are there any barriers you've experienced?
Do you have all the necessary tools and resources to carry out your tasks effectively? Is there a better software, technology, or tool we could use to collaborate remotely?
Do you feel you have the autonomy and trust to manage your work effectively while remote? Are there any areas where you feel more or less empowered?
Are there times when you feel disconnected or isolated from the team's culture while working remotely? If so, what do you think could help alleviate that feeling?
How do you think our team could enhance its remote communication practices to ensure everyone stays engaged and informed?
Which ways do you use to build relationships and collaborate with our team members while remote? Are there any challenges in maintaining effective communication?
How engaged and focused are you able to be working from home? What causes distractions?
Have you encountered any remote work-related obstacles that you feel the team could address collectively?
Do you feel informed on updates and included in team decisions when working remotely?
What best practices have you discovered that help you stay productive in a remote environment?
Are there opportunities for virtual team-building activities or social interactions that you believe would benefit the team's cohesion?
Have you been able to maintain a healthy work-life balance while working remotely?
What measures could we put in place to ensure that remote work doesn't lead to feelings of burnout or overwork?
How often would you ideally like to meet in person as a team?

Questions to explore personal motivation and encourage autonomy

What aspects of your role make you feel that you're making a meaningful impact on the team's success?
What current project or responsibility gets you most excited to work on?
If you could choose one project to take the lead on, what would it be and why?
Do you feel you have enough autonomy in how you do your daily work?
What are your thoughts on the level of decision-making authority you currently have? Is there anything you'd like to change?
Are there areas where you think you could contribute more, given the opportunity?
What factors positively influence your job satisfaction and engagement?
How could we structure your role to give you more flexibility and ownership?
What gives you a sense of purpose in your daily work?
If you could change anything about your current role, what would it be?
What daily frustrations could be removed to increase your motivation?
What gives you a feeling of accomplishment at the end of the day?
Do you feel supported in trying new initiatives?
What would you say is your proudest achievement or contribution since you joined the team?
Are there areas within your current role where you feel you have more to offer but haven't had the opportunity to showcase them?

Questions to ask before closing your 1:1

What's your biggest takeaway from our discussion today?
Is there anything else on your mind I should know about?
What topic or issue should we make sure to discuss at our next one-on-one?
How would you assess our meeting today - are we making good use of our time together?
Is there any way I can improve these discussions to be more valuable for you?
Now that we're wrapping up, what's top of mind for you heading into next week?
Knowing what we just discussed, what's one thing you will focus on this week?
Do you feel like you have what you need from me to go out and excel after our discussion today?
I enjoyed our conversation. Moving forward, what's the most important thing I can do to support you?
Now that we're done, do you feel this was a good use of your time today?
What's one insight or takeaway you have from our discussion today that you will reflect on going forward?