In my previous post on how to hold one-on-ones, I abstracted different conversations that may come up into categories and types. As a refresher, I’ve noted them again here.
| Categories | Types |
|---|---|
| Check-in | Work progress |
| Check-in | Employee engagement |
| Check-in | Mental and physical well-being |
| Discussions | Company and team goals |
| Discussions | Relationship management |
| Feedback | Continued growth and development |
| Feedback | Performance goals |
| Feedback | Upward to manager |
| Feedback | Upward to organization |
Based on this distillation, I’ve put together 103 questions that can be used in your one-on-ones with your direct report. If you’d like more actionable posts to add to your manager toolkit, subscribe to receive notifications.
Work progress check-in
- How are you doing?
- How was the past week/2-weeks/month?
- What’s been the most exciting progress you’ve made?
- What’s been the most frustrating experience in the past week/2 weeks/month? How can I help? What can we start or stop doing to make it less frustrating?
- What are the roadblocks you’re stuck on?
- What’s getting in the way of making your work easier (e.g., clunky processes, too many tasks to juggle at once, slow decision making)?
- What’s your biggest time suck?
- Do you feel comfortable asking for help? Why or why not?
- When was the last time you wished you had some help, but didn’t get it? What happened?
- What can I do to help?
Engagement check-in
- What do you least prefer doing? Why?
- What keeps you engaged and energized? Why?
- What do you do when you’re not as engaged or energized?
- Do you feel like you have enough agency to work independently? How can we empower you further?
- Do you feel like you have enough time to reflect on your work? Tell me more.
- Do you feel challenged at work? In what way? How do you feel about those challenges?
- Do you feel heard?
- When is the last time you’ve seen changes in the team/organization based on what you and others have voiced?
- Do you feel respected?
- Are there any discussions you feel you should be included in but are missing out on?
Well-being check-in
- Are you happy here?
- Are you happy with your current work?
- How would you rate your work/life balance right now?
- Is your current pace of work sustainable?
- What’s something we can change at work that would drastically improve your quality of life?
- Are you taking any time off soon to unwind?
- Do you have sufficient time blocked off in the day to work without distractions?
- Are there any meetings that I can take off your plate? Or remove entirely?
- What can I do to reduce Sunday scaries?
- Have you had enough down time to do something you enjoy outside of work?
Group goals discussion
- How do you think our team is bringing value?
- Tell me how we’ve set our objectives. Does it make sense?
- How do you think our previous objectives went? Do you think we achieved what we set out to do?
- Let’s review the company and team roadmap, objectives, and priorities. (Okay, so this isn’t really a question, but important nonetheless!)
- Based on your understanding of the roadmap/objectives/priorities, what do you think are the next steps?
- Are you clear on how your role fits into the group goals?
- Are the expectations clear and realistic?
- What are your takeaways on the most important work our team must do?
- Do you feel connected to the company and team goals? How so?
- What are some things I can help clarify?
Relationship management discussion
- How do you feel about working with [teammates]?
- Who’s the most difficult to work with? Why?
- Who’s the easiest to work with? Why?
- How do you feel about collaboration with your teammates/stakeholders?
- Is everyone contributing to the work?
- Do you feel like you’re on the same page with your teammates?
- What’s the most difficult part of working with the team?
- What are some things I and/or the other managers can do to make this project easier for everyone involved?
- What do you need from your teammates/stakeholders to keep you motivated at work?
- Do you receive timely and clear feedback from your peers and stakeholders?
Continued growth and development
- I’m curious about [an action or a decision taken]. Can you take me through your thought process?
- What are some other things you can do next time?
- How do you like to receive feedback?
- Do you feel like you’re receiving enough feedback?
- What is the last feedback you got from me that stuck with you? Why did it stick? What can I do to give you similar feedback going forward?
- Do you have any concerns when it comes to opportunities you have here?
- What are some skills you’d like to develop?
- What are some experiences you’d like to be exposed to?
- Do you feel like you’ve had enough time to upskill in the last week/month/quarter/year?
- When was the last time you had a chance to upskill?
Performance goals
- How are you tracking your goals?
- How are you progressing with your goals?
- Are there any roadblocks you’re facing with your goals?
- Do the short-term goals still seem reasonable?
- How do you feel about your long-term goals?
- What part of your current job is most relevant to your long-term goals?
- What kind of opportunities can we discuss that can bring you closer to your long-term goals?
- What are your goals for the next quarter/year?
- What outcomes do you want to realize in 2/5/10 years?
- What can we start, continue, or stop doing to help you achieve your long-term goals?
Manager feedback
- How can I better support you?
- Tell me the last time I said something that didn’t make sense. What happened?
- Do you find my communication simple and easy to understand? If not, what can I improve?
- Do you feel that I’m providing you with enough context on our company and team’s vision, mission, and objectives?
- Have I made goals and expectations clear for you?
- Do you feel empowered?
- Do you feel like we’ve spent enough time discussing your career development?
- When was the last time you felt lost? What could I have done to help?
- What can I start, continue, and stop doing to improve our relationship?
- What is your ideal management style? What’s one thing I can do now to mirror your ideal style?
Organization feedback
- How can the company better support you?
- Do you find the company town halls/all-hands to be inspiring? Do you leave with a clear understanding of where we’re going as an organization?
- Do you have the right equipment and support needed to succeed at your job?
- What are your favorite parts of our company culture? Team culture?
- Are there any “traditions” you’ve seen in other teams or companies that would be great to adopt here?
- What’s your biggest gripe about our company? Our team?
- Do you feel like the organization takes your opinion seriously?
- What can our team start/continue/stop doing to be more effective?
- What does your ideal company or team culture look like?
- What do you think is our biggest problem at this organization?
Water cooler chat
- How’s life?
- What’s the most exciting thing happening outside of work?
- When is your next vacation? What will you do? Or what do you want to do?
- What’s the last movie/book/podcast/song you enjoyed?
- How’s your fur/plant/human baby?
- How’s your [insert hobby] going?
- Is a hotdog a sandwich?
- What’s your opinion on Hawaiian pizza?
- Are fruits legitimate toppings for an ice cream sundae?
- What’s the best style of pizza?
I pulled these questions from old questions I’ve asked at work before. I’m seeing a pattern here: I love food and I like to sow mild discord.
Recurring questions
- Any follow-ups from our last one-on-one?
- What do I need to do before our next one-on-one?
- What do you need to do before our next one-on-one?