PROJECT

Headway

A simple guidebook to running more human (and more effective) 1:1 meetings.

outcomes
Writing & Editing

UI Design

Development

Testing & UX

the challenge

If you’re not familiar with them, one-on-one meetings are a chance for a team member and a manager to get together and focus completely on the team member and her struggles, goals, and concerns. I find these meetings fascinating because they had such a huge impact on me, both as a team member and as a manager.

The hardest part about starting out as a manager holding one-on-ones is that there’s no single place to learn more about them. Tips and recommendations are spread out across dozens of articles and blog posts, and some of the advice is conflicting. It can be tough to know exactly what to talk about and how to know if you’re doing a good job. A lot of the time it felt like I was just winging it, which wasn’t very efficient.

After talking with a lot of other managers, reading countless articles and blog posts, and running 100s of one-on-ones myself (and making lots of mistakes!), I realized that these meetings don’t have to be scary or complicated.

There’s an easier way, one that doesn’t rely on notes or agendas. And it all starts with accepting the complexities of being human, rather than trying to optimize our way around them.

My goal with this guidebook is to pare everything down into a quick, easy-to-digest format. If you’re new to these types of meetings, this book will give you a two-year head start. If you’ve been doing them for a while, you’ll find ideas in here to challenge how you approach them and what you — and your team — should be getting out of them.