My 1-on-1 starter prompts

CJ Cenizal -

When I first started having 1-on-1s with my manager, I didn't know what to talk about. The thread of the conversation randomly touched on status updates, weekend plans, random life things, but I didn't really know what the point of this time was. Eventually, mercifully, the meeting would end and we'd get back to work. Not fun.

Fortunately, my 1-on-1 game improved over time. I started to use my manager as a resource to help me navigate the invisible currents of the company, understand where I could contribute most meaningfully, and ultimately shape my career.

After I became a manager, I found myself introducing new hires to the productive 1-on-1 patterns that I had developed as an individual contributor. To save time I wrote down some 1-on-1 starter prompts, inspired by the "What to talk about in 1:1s" comic strip by Julia Evans, to help guide our conversations in productive directions.

Give these prompts a shot if you ever find yourself running out of things to talk about during your own 1-on-1s with your manager. If you're a manager yourself, consider sharing them with your team members if you suspect any of them feel unsure about what to discuss with you.

A comic strip that suggests 1-on-1 topics, by Julia Evans (https://wizardzines.com/comics/1-1s/)

Career development

  • Where do you want to go in your career? Share your aspirations. Maybe you want to be promoted, switch career tracks, or eventually found your own startup. A good manager will look for opportunities to help you progress towards these goals because they know these will give you job satisfaction, which will help you do better work.
  • What kind of skills and experience do you need to develop to get there? Your manager might be able to provide some guidance and feedback based on what they've observed from your current set of capabilities.
  • How can your manager find opportunities for you to develop these skills and experience? A manager on top of their game will be looking for these already, but everybody needs nudges sometimes. Sometimes you might need to directly ask your manager for sponsorship.

Technical and product

  • Do you want to discuss any software design or architecture topics? Even if your manager is no longer very technical, this can be a useful communication exercise and the questions your manager asks might expose you to new ways of approaching a problem.
  • Do you want to discuss any product design and UX design topics? If your manager is more product-oriented (like I am) then you can pick their brain about the user-facing decisions you make when building features.
  • Do you want to bounce around ideas for new features? Good managers are forward-thinkers and will be thinking about where the team is headed and what they'll be working on. This is a great way to influence this work at an early stage, and possibly prepare yourself to lead it.
  • Any questions about the direction/vision of the team, organization, or your products? Same as above.
  • Do you have any concerns about technical debt? Most engineers have strong opinions on technical debt because it causes them pain on a daily basis. Engineering managers who haven't stepped on a code landmine in awhile might have become desensitized to this pain. So do your manager a favor: vent to them about it. Just be prepared for them to probe deeper, to understand the impact on the team's ability to ship features or fix bugs.
  • Does the team need to hire anyone with specific skill sets or experience? Similar to technical debt, but for the team. If you wish there was a specialist on the team who could free you up to specialize on something else or if the absence of this person is creating problems, then your manager will want to know.
  • Do you need your manager to clarify or adjust any roles or role relationships? Maybe there's a new hire on the team who specializes in nump-crunking 2.0, and you just can't take this person seriously when they try to talk about it with you. Or maybe you've never worked with a product manager before, so you're not sure how to share the workload. Your manager can help you recognize the value in unfamiliar roles and figure out how to work with them effectively.
  • Is there an issue you’re having with another team member that you’d like to discuss? It's a manager's job to help the team gel. Once you make your manager aware of the issue they can figure out how to help you resolve it.
  • Is there anything the team should be doing differently, more of, or less of? Managers aren't omniscient, and you can help them see into their blindspots by suggesting ways the team can improve code review, on-call, interviewing, and other processes.

Feedback for the manager

  • What's your manager doing well? You can encourage your manager to do more of this by showing your appreciation. Be specific about the positive impact your manager made with this behavior. "Hey, I just wanted to say thanks for clarifying our roadmap at our last sync meeting. That gave me better insight into our long-term goals, and as a result I was able to pay down some tech debt that will help us reach them."
  • Is there anything you'd like your manager to improve on? You can provide coaching to help them work on this area: "When you shared our roadmap at our sync meeting, I didn't see any specific dates. I was hoping to see a rough timeline so I could prioritize our tech debt backlog based on how long each item could take. Would it be possible to update the roadmap with this info?"
  • Would you like to see your manager change the way they work with you or others? "I saw that you rescheduled our last two 1-on-1s at the last minute. This tends to throw me out of the flow and makes it hard for me to get back up to speed on the work I have in-progress. Is there a new fixed time we can use that will be more convenient for you?"
  • Is there something your manager is working on that you'd like to learn more about? It could be that you'd like to learn more about how they approach a specific type of problem, or you'd simply like more visibility into their day-to-day.

If you ever feel like your 1-on-1s could use more direction and aren't quite providing you with the value you're looking for, try these prompts out and see if they help. Remember, your manager should be a resource to you and 1-on-1s are your time. Make it count!

Further reading

Julia Evans published a great PDF called "Help! I have a manager!" that's all about how to understand your manager's job and how to work with them more effectively. If you liked her comic at the beginning of this post, you'll love this PDF. It's full of more great stuff like that, and it only costs $10.

She also wrote a blog post called "Things your manager might not know", which is rich with topics you can discuss in your 1-on-1s.