Excited to announce HEADWAY: A Practical Guide to Running One-On-Ones for Humans

When I decided to move on from Buffer, one thing that I really wanted to do was to share as much of what I had learned during my time there as I could.

I thought a lot about what would be valuable and useful to other people. I came up with a few ideas, but the one I kept coming back to was about sharing what I learned about running one-on-ones that tackled the deep and complex issues we all face but don’t often talk about.

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.

Below is the introduction to Headway, which is available for 50% off during the pre-order.


Let’s stop calling them one-on-ones

I’m pretty sure that one of the best ways to get someone to dread something is to call it a “one-on-one meeting.”

I was anxious when I first heard the term. It sounds a little bit like punishment, like you’re being called into the principal’s office again. The only difference is that this time you have much more at stake.

Of course, as soon as I had my first one-on-one and I realized how powerful it could be, I was hooked. Who wouldn’t want a dedicated time to talk about larger challenges with their manager and mentor? It’s a dream come true! In fact, one-on-ones have probably had more impact on my personal growth in the past few years than just about anything else I’ve done.

But the term “one-on-one” leaves all of that potential out. It implies that what’s special about these meetings is that they’re face-to-face—but of course we’ve all had face-to-face meetings that don’t seem to go anywhere. If you asked someone who hasn’t heard the term, they’d probably tell you that they have one-on-one chats with their manager all the time. What’s exceptional about these types of meetings isn’t their format.

The name also tells you absolutely nothing about what its purpose is. Is it for the benefit of the team member? The manager? The business? Are you discussing performance, or something else?

It shouldn’t be an extraordinary thing to have 1:1 time with your manager. It should be an extraordinary thing to have time with your manager to help you break down challenges and keep moving forward in your life.

I think it’s time for a new term. Let’s ditch the one-on-one in favor of something clearer. Something that celebrates the purpose of these types of meetings: a focus on growing great people, overcoming difficulties, and helping your team make headway in their lives even in the face of their greatest challenges.

In fact, headway would be a much more appropriate name for these meetings than one-on-one. Headway can be defined as, “To move forward or make progress, especially when circumstances make this slow or difficult.” A headway meeting, then, would be a chance for managers to get together with team members and collaboratively work on moving forward despite the challenges that may exist.

Headways are a different way of thinking about one-on-ones. Less formulaic, more substantive. Both the manager and team member can call them when they’re needed, instead of fixing them to a recurring calendar reminder. And they embrace the complexities of being a fully rounded human being by prioritizing the person instead of the work or the output. (Businesses already have plenty of mechanisms for taking care of those things.)

Most of all, though, headways give people a little more grace because they assume, by default, that you’re struggling—and that you’re not alone.

That sounds like a meeting I’d be excited to show up for.


This was an excerpt from my first book, Headway. Enter the code PREORDER50 to get 50% off while it’s in pre-order!