As a manager I read blog posts all of the time on how to have better 1:1s, but I remember being frustrated as an individual contributor that I couldn't find anything for the other way around. My 1:1s were often ending early, consisting mostly of status updates that could have been an email, and seeming like a waste of everyone’s time. (Managers, this is also on you, by the way.)

My managers had created psychological safety, but as a junior engineer I didn't always know what to do with the space when they created it for me. And to be honest, I didn’t really know what all my manager did or the kinds of decisions they were making all of the time. These kinds of questions and conversations helped me get a much deeper appreciation for what they did every day. I got insight into why they might have made a different trade-off than I would have, and it helped me become a better engineer. Now as a manager and a manager of managers myself, I really love when I can see people thinking this deeply about their work and wanting to partner on exploring it further.

It took me a while to get good at asking my own manager questions, and I realized that was mostly a result of good mentoring by others. When I heard from other senior women on what they had asked for- especially things I had never considered- I felt more comfortable getting creative in talking to my own manager.  The list below is, in fact, now the number one resource my mentees pass on to others.

So here are some examples of questions and discussions I’ve found helpful. This isn’t an exhaustive list; it’s a jumping off point. Managers that see me share this list often ask me if there’s an answer key that goes with it. Nope, sorry, but it can be a good management exercise to see what you think you could or couldn’t answer in the moment if one of your reports started asking questions off of these kinds of lists.

Career Development

• How can I grow more in my role?
• Can we talk about different job ladders that I might be interested in?
• I need a change. Are there other roles for me in the org?
• I want to explore or develop skills in a certain area. Can we identify or create opportunities for me here?
• How am I progressing on previous career or perf feedback?
• What development opportunities are available that make sense for my goals? (Ex. joining a more senior meeting, attending a conference, signing up for a training)
• I admire X person’s career path (or multiple people). How do I design a career for me like that?
• I’m not sure what I want next. What are some options?
• I really like/don’t like my role. Can we discuss how to do more/less of that?

Team Dynamics

• How do I work better with <a particular Teammate>?
• I had this awkward/uncomfortable/frustrating situation that I’d like to solve or that I want you to know about. Can we walk through it?
• Can we better define roles and responsibilities in this area that’s unclear?
• I think this project is understaffed and here’s why. Can I get more hands for this next quarter?
• How should the relationship with this collection of people work? (Ex. Project Lead, Product Manager, Collaborator, etc.)
• I’m concerned about someone on the team. Can I help make sure they’re supported?
• There was a recent team interaction that was surprising that I’d like you to be aware of. Can we find ways to make that better in the future?
• This project is experiencing problems. What skills are missing to help ensure its success?
• What are the succession plans if you/our leads/someone on the team leaves?
• Can we do more social events or fun time?
• It seems like Glue Work is falling to the same group of people on the team. Can we better distribute that work?

Technical Challenges

• I’m struggling with a choice between A, B, and C. Can you see if I’m missing something?
• Can you help me get unblocked from this approval or review?
• This policy is causing issues. What are our options for satisfying it or changing it?
• I feel overwhelmed in this space. How can I understand this tool/topic/space better?
• How can I take this idea and make it useful for more people?
• Do you think this is solving the correct problem?
• What problems do you not have bandwidth to deal with? (Ex. backlog of concerns available)
• I no longer think we should be doing this work and I’d like to reprioritize or cancel something. Can we discuss where this fits (or doesn’t)?
• How do I break down this problem into smaller pieces or multiple projects?
• Can I get a second opinion on this decision?

Organizational Strategy

• What is the long-term plan for this?
• Can you tell me more about this decision?
• Who are good people to talk to in order to learn more about X?
• How does our team fit into the larger organizational vision?
• What are other teams doing to solve these problems?
• What are the motivations behind this move?
• Where is this discussion coming from?
• Can we broadly discuss strategy or help me learn how to think about it?
• Who are the stakeholders for this work?
• Where can I learn more about our roadmap or vision for the team/product?
• Where does the team currently need leadership?
• How is this recent re-org going to affect me or our team?

Prioritization

• I’m overloaded and need to drop 2 things out of this list. What should I drop?
• I’m juggling a lot of balls at the moment. Which are glass and which are rubber? Are there deadlines that I can push back while keeping the work?
• I’m looking to increase scope or have more room for work, can you help me find new work?
• I want different work soon. Can we come up with a plan to change the kind of work I’m doing?
• Is this project making sufficient progress?
• I won’t have time for this project. Can we re-assign it to someone else?

Recognition

• This work was significant and I felt it was under-recognized because….
• I want to make sure a co-worker gets recognized for something they did that you might not otherwise know about. Can you consider a spot bonus for something?
• This particular action made me feel recognized and appreciated. Can we do more of this as a team?
• I do/don’t find this particular work rewarding. Can we talk about what motivates me? (Ex. Motivation discussions)
• Have we thanked _____ recently for the work on ______?
• I wanted to make sure you knew _______ was excelling.

Feedback

• I could use more positive feedback. Could we talk about things you think I’ve done well recently?
• How can I improve in my role? What could I be doing better, do more of, or start doing?
• The last time we talked you mentioned this feedback. The more I sit with it, the better I’d like to understand it. Can we discuss it?
• I disagree with this feedback, and I’d like to explain why and make sure I understand. Can we discuss it?
• I have feedback for a way to improve something on the team. Are there current plans for this?
• I need more ______ out of our manager relationship. Can we schedule more time for it? (Ex: strategic coaching, space to bounce ideas, feedback on something specific)
• I need to give tough feedback to a peer (on or off the team). Can I practice with you?
• There’s a tough conversation coming up that I’d like to prepare for. Can I get feedback on how I’d like to approach it?
• What’s the best way to give $OTHER_LEADER some feedback?
• This feedback invoked a strong reaction (positive or negative), and I’d like advice on how to navigate it better.

Support

• I have a personal situation that is causing extra stress. Can we explore options for adjusting expectations in the short or long term?
• Can you help identify a mentor for me to work on this?
• What resources are available from the company to help me cope with X?
• I’m nervous about this upcoming situation (presentation, launch, etc.). Could you do _____ to support me? (Ex: review a deck, attend the presentation, join a meeting, look at a demo, etc.)
• Someone recently tried to do X to support me but it didn’t actually help or made things worse. Can we talk about how to avoid this going forward?
• Can you help rearrange my schedule to be able to feel like I can take vacation?

Trends and Pulse

• I heard this rumor and it’s making me nervous/anxious/worried. Is it true?
• I saw this in the news and it’s stirring up these feelings for me. What can we do to make that better?
• There was a statement at a presentation that really surprised me. Can you help me understand what’s happening?
• I don’t agree with something the company is doing. What is the best form of escalation?
• Something happened to a group I’m a part of and it doesn’t seem to be affecting the rest of the team. Can we discuss how it’s affecting me?
• I was disappointed with the response to something. Can you share your thoughts or opinions on it?