Most 1-1s follow the same pattern: a status update, a quick check-in, maybe a mention of something that is slightly annoying. That is not a bad meeting, but it is not a great one either. The difference between checking in and genuinely opening up often comes down to the question you ask. A well-chosen question cuts through the surface and gets to the thing the person actually wants to say but has not found the moment to raise. These 50 questions are designed to do exactly that.
The best 1-1 question is one the other person hasn't been asked before.
How to use these questions
Do not read from a list. These questions work best when you choose one or two that feel relevant to where that person is right now. The question that lands for a senior engineer three months into a new project is different from the one that matters for someone who has just come back from leave or who is quietly struggling with confidence.
Keep a few in rotation. Returning to the same categories across meetings helps you track how someone is feeling over time: energy, motivation, blockers. A question about workload in January and again in March can reveal a trend that a one-off conversation would miss entirely.
Adapt the wording. These are starting points. If the formal phrasing feels stiff in your context, change it. What matters is the intent behind the question, not the exact words. Ask it like yourself.
The questions
Wellbeing & energy
- 1.How are you actually doing at the moment, not just work-wise?
- 2.On a scale of one to ten, how would you rate your energy levels this week? What is driving that number?
- 3.Is there anything outside of work that is making things harder right now that I should know about?
- 4.Are you getting enough time to switch off, or does work follow you home at the moment?
- 5.What has felt most draining over the past few weeks?
- 6.What part of your week do you look forward to most?
- 7.Are there any signs of stress or overload that I might not be seeing from the outside?
- 8.If you could change one thing about your working environment to make your day easier, what would it be?
Growth & development
- 9.What skill do you most want to develop in the next six months?
- 10.Are there areas of your role where you feel like you are growing, and areas where you feel stuck?
- 11.Is there anything you are working on that is stretching you in a good way right now?
- 12.What kind of work would you like to be doing more of?
- 13.Are there opportunities you feel you are missing out on that you would like to explore?
- 14.What has been the most useful thing you have learned recently, and where did it come from?
- 15.Where do you see yourself in two years, and is your current role moving you in that direction?
- 16.Is there anything I can do to better support your development at the moment?
Work & blockers
- 17.What is going particularly well with your work right now?
- 18.What is slowing you down most at the moment?
- 19.Is there anything you are waiting on from me or the wider team that is blocking progress?
- 20.Are there any recurring frustrations in your work that we have not properly addressed?
- 21.What would make the biggest practical difference to how productive you feel day to day?
- 22.Is there a piece of work you are particularly proud of recently?
- 23.Are there any decisions being made that affect your work that you feel out of the loop on?
- 24.What is one thing I could stop doing, start doing, or do differently that would help you?
Team & relationships
- 25.How are you finding the team dynamic at the moment?
- 26.Is there anyone in the team you feel you work particularly well with, and why?
- 27.Are there any tensions or friction points in the team that you think need addressing?
- 28.Do you feel like you get enough visibility and credit for the work you contribute?
- 29.Is there anything about how the team communicates or collaborates that is not working for you?
- 30.Do you feel included in the conversations and decisions that affect your work?
- 31.Is there a colleague you would benefit from working more closely with?
- 32.If you could change one thing about how our team operates, what would it be?
Feedback & direction
- 33.How clear do you feel on what is expected of you right now?
- 34.Is there feedback you have been wanting to give me that you have not had the chance to?
- 35.Do you feel like you get enough feedback from me about your performance?
- 36.Is there any feedback or guidance you are looking for that you are not currently getting?
- 37.How useful do you find our 1-1s? Is there anything you would change about how we run them?
- 38.Do you feel like your priorities and mine are aligned, or are there gaps?
- 39.Is there an area of your work where you would value more autonomy?
- 40.Are there ways I am unintentionally making your job harder?
Big picture
- 41.What motivates you most about your work right now?
- 42.What would make you feel genuinely proud of what you have accomplished by the end of this year?
- 43.Is there a type of problem you would love to work on that you have not had the chance to tackle yet?
- 44.If you were designing your ideal role, what would be different about it compared to your current one?
- 45.What does success look like to you, not just professionally, but in terms of how you want to feel about your work?
- 46.Is there anything about the direction the team or company is taking that you are uncertain about?
- 47.What is one thing about your work that you think others underestimate or do not fully appreciate?
- 48.If you had to give me one piece of advice about how I could be a better manager to you, what would it be?
- 49.What would need to be true for you to still be here and thriving in two years' time?
- 50.What is one thing we have talked about over our 1-1s that you feel has never been properly resolved?
Keeping track of what comes up
A good answer does not do much if you have forgotten it by next week. The things that surface in a 1-1, like a goal someone mentioned, a concern they raised, or a blocker they flagged, need to go somewhere so you can come back to them. That means logging notes after the meeting, not just promising yourself you will remember.
The follow-through is what builds trust. If you asked someone about their development goals and they told you they want to get into more technical writing, and then three months pass with no mention of it, that person stops sharing things. But if you come back to it, even just to say you have not forgotten, that changes the dynamic completely.
Manager Toolkit's catchups feature lets you log notes against each 1-1, create actions directly from the conversation, and surface previous topics before your next meeting. You do not need to rely on memory or search through old documents. What was said last time is right there when you need it. Use Key Themes to tag patterns across your 1-1s-if wellbeing or growth keeps coming up with the same person, you will see the trend without searching through notes.
Log what comes up
Capture notes from every 1-1 and surface them automatically before the next one.