How we approach 1:1s with the technical team

For the first years of Playground’s existence we were afraid of too much management, of too much process. We’re all smart, capable and busy people. Let’s stay out of the way so folks can get their work done. If they need something, they’ll say something, right?

Maybe that works with a small team. A team that’s been there since the early days. Conversations are ad-hoc and we all learn by osmosis. But it doesn’t scale.

And how do you scale? By being intentional. By making space.

Having regular 1:1s is a practice that opens doors, that builds relationships. It’s never the only line of communication, but it provides a guaranteed time and place to connect.

Ok, so what are we talking about anyway

Ideally, a 1:1 should be led by your report. You have created a space where they can be comfortable expressing themselves and communicating with you about what’s really going on. How exactly to do that is probably beyond the scope of this post, but it’s a slow process of building trust and proving worthy of keeping that trust.

1:1s will likely be different with different people, and that’s okay. They may ebb and flow with the same person too. Maybe this time you need an hour, or maybe just five minutes. As long as you’re both communicating with each other, you’re good.

Until you’ve established a rhythm and cadence, it will be useful to provide an initial structure from which to work. It will also be useful to circle back on particular themes once you have a natural flow too.

A general structure

Pick and choose as you need and feel free to make it your own. Not all questions will be necessary at all meetings. These are presented in an order that seems to work, but there’s no need to be strict.

Getting started

Small talk. Love small talk.

Honestly, this is an important part of building that trust we were talking about earlier. This is an opportunity to demonstrate that you care, that you’re interested.

Following up

Anything brought up in a past 1:1 that requires revisiting.

Did I say I would take care of something or look into something?

  • Here’s where we talk about how that went and any potential next steps.

Did they say they would work on something or look into something?

  • How is it going? What’s next?

Checking in


  • How are you doing?
  • How do you feel about the project you’re working on?
  • What’s it like working with the project team?
  • How are you feeling about X’s leadership on the project?
  • What’s it like working with the client?
  • Is there anything you’re concerned about?


  • Is there anything I can do to help you?

Rarely do people have a specific ask in response to this very open question.

Usually this kind of help can be identified in the context of answers to other questions. Maybe I help them think through a possible solution to a problem they’re facing. Or maybe I can see that there’s something going on that I should take the initiative on and deal with. A more specific offer, “Could doing X help solve Y?” can be very productive.

I think it’s still good to ask the open question straight up. And to ask it regularly.

  • Is there something I’m not doing that I could be doing?
  • Is there something I’m doing that I shouldn’t be?

People really seem to appreciate these questions. Again, maybe there isn’t always much that comes up but being open to and making space for feedback is important.

Big picture

  • How are you feeling about Playground?
  • How do you feel about your role here? The work that you’re doing?
  • Is there anything about the company that you’re worried about?
  • Is there anything we’re not paying attention to that we should be?


  • We’ve set some goals back at the performance review. Where are we at?
  • Does anything need to change?
  • What are next steps?


  • What am I working on?

This may or may not be directly relevant and that’s ok.

  • What am I thinking about or planning for the longer term?
  • Is there something specific I’m working on that I can share and invite feedback on?


Did something happen that’s worth celebrating? Did something happen that needs correcting? Did a client or team member say something nice about the person I’m meeting with and can I share it with them? Is there something I’m concerned about? How are we doing with professional goals? With the points in our performance matrix?

Always following positive feedback with negative feedback can establish a pattern where the positive gets negated, because the person is just waiting for the negative. Be careful about this.


How are things otherwise? Maybe this is just more small talk. Or maybe there’s room to talk about bigger or more personal things, if the person feels comfortable. Never push for it, but make room if it needs to happen. Be a support. Build rapport. Maybe share something too, if appropriate.

Is there something big going on in their life? Could this affect work in some way? Is there something we can offer that might help?

An offer of help must only be something that can be delivered upon. Don’t make promises you can’t keep.

Wrapping up

Summarize the session. How is the person feeling? What are the challenges that we’ve identified and what steps are we taking to address them?

So people know they’ve been heard.

Reminder that I’m available to chat or support or work through anything outside of 1:1s.

Thanks for checking in!

Troubleshooting & tools

1:1s can include brief status updates, but that shouldn’t be the main focus. It’s about checking in, giving and receiving feedback, discussing performance, following up on goals people have set, and identifying opportunities for growth. They can also be a place to work through difficult problems, whether technical/design or interpersonal. But when it comes to working through interpersonal problems or challenges, how exactly do we do that?


If we’ve identified that the person needs to have a difficult conversation with someone and isn’t super clear on how to proceed, offer up a safe space to practice that conversation. Play the part of the person they have to talk to and try out the conversation. If it would be helpful, you can offer also to switch parts. Take a step back and break down the conversation. How did it go? How did it feel? What could be better?

It’s good to identify and brainstorm different ways of approaching the conversation, but let’s not be prescriptive. We can coach people and help them figure out how to handle what’s going on, but let’s not tell them a specific way as if it were the only way. There are ways.

Scenario analysis

Is there something big coming up, around which there’s uncertainty or anxiety? Let’s work through it.

What’s the worst possible thing that could happen? How will you feel when that happens? How might you respond? Is this even a likely scenario that could happen? Or is it a product of fear?

What’s the best possible thing that could happen? What does that look like? What’s the likelihood of things going this way?

What probably is the thing that’s going to happen? How will that feel? How will you respond? Do you feel equipped to respond?


1:1s as a practice

It will take time. Time to get to where you’re going. And time to figure out where it is anyway that you’re going to be going. Take that time.

With thanks to Mike Ferrier who years ago shared a framework that the above is built upon. Nicole Chung for the thoughtful feedback.