Chapter 4
One-to-Ones

This afternoon you begin your one-to-ones with your team. You’ve got three of them booked in today: Ben, Katie, and Lee. Your initial meetings with them last week went swimmingly, but you were mostly just gathering information about their roles within the team and the projects that they are working on. Today it’s down to business, and you’re feeling the stage fright.

To the content: you had a bunch of ideas last night that felt inspirational, motivating, and life-affirming. But on reflection this morning, they seem awkward, cheesy, and dumb. You nervously tap your fingers on your knee. You want to get these relationships off to the right start. You worry you’re going to be spending several hours sitting in painful on-off silences. What if you don’t have anything interesting to say? And what are you even meant to be saying? Your previous manager was broadly absent, so you don’t have experiences from the other side of the table to model. You begin to get a bit worried.

Taking out your phone, you Google “what to talk about in one-to-ones.” You scan the results from the many listicles that populate the first page of hits. “Self-critique”? It’s a bit early to dive into that. “Check in on objectives”? Well, you haven’t really set any with anyone yet. “Talk about pay”? Erm, that doesn’t seem like a normal first meeting. “Coaching”? But on what? You still need to get to know these folks first before you can get into a rhythm of meaningful conversation.

You hop off the subway at your downtown stop. Ascending the station stairs and emerging onto the street, you hope for an epiphany, otherwise it’s going to be an extremely awkward afternoon. As the traffic noise of the city swirls, you can’t help but tune in to a loud conversation happening between a pair of suited men walking in front of you.

“So did they get the contract?”

“Yeah. We had to make some amends and also walk back on some of the pricing, but it’s signed.”

“Nice job. What were some of the changes?”

“Nothing major. They want some regular support from our services team, which isn’t a big deal. They also want a QBR, plus the terms to be re-evaluated at the end of the year.”

You reach the crosswalk and wait for the traffic to stop. If only you could have a contract with your direct reports about what each side needs from the relationship, you think. The light turns green. You step out into the road. That’d make things easier at the start. Hang on a second. This sounds like a good idea...

In this chapter, you’re going to learn how to do one-to-one meetings with your staff. Although you may be wondering how this subject can generate an entire chapter of content, I can assure you of the following:

• That you’re going to be spending a lot of time in one-to-ones, so it’s in your best interest to be able to do them confidently, comfortably, and to get the most out of them.

• That there is a vast difference between having an unprepared chat and having a meaningful, focused one-to-one.

So that’s what this chapter is here for: to give you the context, techniques, and inspiration that you need to have great one-to-ones.

In this chapter you’re going to learn the following:

• How to best prepare for one-to-ones, again touching on why they’re an essential part of your role.

• How to do your first one-to-ones by using an exercise called contracting in order to get your relationship off on the right foot.

• Ideas for what to talk about each week, including how much you should actively participate versus passively listening.

• How to take notes and assign actions. I’ll show you the system that I use to do it so that you don’t forget anything.

OK, are you ready? Let’s get going.