Square’s 1-on-1 Toolkit: The secret to managing your team’s careers
1-on-1 Toolkit

icon picker
Partnership Agreement

This first section is all about setting expectations and start a conversation about how you’d like to run your one-on-one sessions.

Company operating principles

At Square, our company's operating principles are...

Team member expectations

I’m at my best when: I have plenty of heads down project-work time, but can ping someone for quick zoom sessions to discuss. I also appreciate knowing when things I’m doing land well. I’m better at work if I can get exercise in twice a week and turn off after Xpm.
My preferred place or format for one-on-ones: I think best [outside on a walk, by a whiteboard, ...], can we have our one-on-ones there...
Areas I want to develop: I'd love coaching on [...]
discussions: I’d like to discuss progress towards my career goals by [format] every [frequency]
My preferred feedback style and cadence: I do best when I receive lots of reinforcement on what’s going well, but also want to know where I can improve. I prefer timely and concrete feedback. The easiest way for me to receive it/ is [in person, over slack, email, etc] in [direct, sandwiched, etc] style.

Manager expectations

Goal for one-on-ones broadly: I’d like these one-on-ones to make you feel supported and heard. I want you to come away feeling like you can tackle the most important problems on your plate, and I’ll be there to back you up. Please raise any blockers you’re seeing towards your progress. We’ll also use these one-on-ones as a place to give encouragement and feedback (both ways!) and check in on your career growth (at the cadence you prefer).
My expectations of you: I expect you to set your own agenda, track your own notes, and manage follow-ups from our one-on-ones. I will add thoughts from time to time, but the agenda is primarily yours. I’d love for us to figure out the right cadence for more in depth feedback, but please plan to give me feedback on what you need more of or less of from me each week.
One of my weaknesses is: [...] so please call me out if you see that happening
Feedback from you: Each time we meet I'll ask what you need more of and less of from me so I can adjust to best support you. I prefer to receive feedback in this way [...]

Our shared expectations

Cadence: Let’s do our best to meet every [...]. If one of us has a conflict we will [reschedule, cancel].
Agenda: The agenda for each one-on-one should be set by [time] before our meeting by [team member and/or manager].
Topics: Every [insert time], we will review goals in and every [insert time] we will review performance in the section.
Feedback: Let’s give each other feedback in [style] way and [type of] form
Wins: Let’s celebrate wins in this way [...]

👉 Next:

Want to print your doc?
This is not the way.
Try clicking the ⋯ next to your doc name or using a keyboard shortcut (
) instead.