75+ questions forbetter 1:1s

What skills would you like to develop over the next quarter?

Where do you see yourself in the next 2-3 years?

What type of projects would help you grow the most?

Are there any training or learning opportunities you're interested in?

What aspects of your role do you find most fulfilling?

Is there a role or responsibility you'd like to take on?

Who in the organization would you like to learn from?

What's one thing you'd change about your current role?

How can I better support your career development?

What accomplishment are you most proud of recently?

Are you getting enough opportunities to stretch your abilities?

What would make this job your dream role?

How aligned do you feel your work is with your long-term goals?

What's something new you learned recently that excited you?

If you could shadow anyone in the company for a day, who would it be?

What feedback have you received lately that was helpful?

Is there any feedback you've been wanting to share with me?

How do you prefer to receive feedback?

What could I do differently to better support you?

Is there anything I should start, stop, or continue doing?

How can we improve our 1:1 meetings?

What feedback would help you improve in your role?

Are you getting enough feedback from your peers?

What's something you wish you had known earlier in this role?

How well do you feel recognized for your contributions?

What feedback from a past manager has stuck with you?

Is there a recent situation where you would have appreciated more feedback?

What's the biggest obstacle you're facing right now?

Is there anything slowing down your work that I can help with?

What process or tool frustrates you the most?

Are there any unclear expectations causing friction?

What's something that's harder than it should be?

Are there any decisions you're waiting on?

What would help you be more productive?

Is there any information you're missing that would help?

What's something you wish you could delegate?

Are there any team dynamics causing challenges?

What are your top priorities for this week?

How are you progressing on your quarterly goals?

What would success look like for you this month?

Are your current priorities aligned with what matters most?

What's one thing you want to accomplish before our next 1:1?

Is there anything on your plate that shouldn't be a priority?

What goal are you most excited about right now?

How can I help remove barriers to achieving your goals?

What's the most important thing you're working on?

Are there conflicting priorities you need help resolving?

What would you focus on if you had more time?

How do you decide what to work on each day?

How would you describe our team culture?

What do you think makes our team effective?

Is there anything about the team dynamics you'd like to improve?

How well do you feel connected to the broader team?

What could we do to improve collaboration?

Is there anyone on the team you'd like to work with more?

How inclusive do you feel our team is?

What's something you appreciate about your teammates?

Are there any unspoken tensions on the team?

What would make our team meetings more valuable?

How are you doing, really?

What's something exciting happening in your life outside work?

How are you feeling about your work-life balance?

What helps you recharge outside of work?

Is there anything affecting your energy or motivation?

What's something you're looking forward to?

How supported do you feel at work?

Is there anything personal I should be aware of that might affect your work?

How can I be a better manager for you?

What do I do that helps you the most?

What do I do that's frustrating or unhelpful?

Am I giving you enough context about company decisions?

Do you feel you have enough autonomy in your work?

How clear are my expectations for your role?

Is there anything I should communicate more openly about?

Do you feel I advocate for you and the team?

What could I do to help you feel more engaged?

If you were in my position, what would you do differently?

How is your remote work setup working for you?

Do you feel as connected to the team working remotely?

What's the biggest challenge of working remotely for you?

Are there any tools or resources that would help you work better remotely?

How do you maintain boundaries between work and personal life at home?

Do you feel you get enough face time with teammates?

What aspects of remote work do you enjoy most?

Are there any communication gaps we should address?

How can we improve our async communication practices?

Would you prefer more or fewer video calls in your typical week?

What's been the most surprising thing about joining the team?

Is there anything about our processes that confuses you?

Do you have the access and tools you need to do your job?

How clear are you on your role and expectations?

Who has been most helpful to you since you started?

What questions do you still have about the company or team?

Is there anything from your previous experience we should adopt here?

How can I help make your transition smoother?

What achievements are you most proud of this period?

Where do you feel you've grown the most?

What goals did you struggle to achieve and why?

How do you feel about the quality of your work lately?

What would you do differently if you could redo the past quarter?

How well did our performance expectations align with reality?

What support would have helped you perform better?

Where do you want to focus your development next?

How do you think your peers would describe your contributions?

What obstacles kept you from performing at your best?

How aligned do you feel with the company's direction?

What's working well on your team that I should know about?

Is there anything you'd tell me that you wouldn't tell your manager?

How could leadership better support your team?

What changes would have the biggest impact on your work?

Do you feel you have enough visibility into company decisions?

What's one thing you'd change about our organization?

How is your relationship with your direct manager going?

What's your understanding of the situation?

How has this situation affected your work?

What would a good resolution look like to you?

What do you think the other person's perspective might be?

What have you tried so far to resolve this?

What support do you need from me to move forward?

What went well on this project that we should repeat?

What would you do differently next time?

Where did we underestimate complexity or time?

How effective was our communication during the project?

What was the biggest surprise or learning?

How well did we handle unexpected challenges?

What risks did we miss that we should watch for next time?

What process improvements would help future projects?