On Skip 1:1s

One of the first things I did as a new manager of managers was schedule skip 1:1s with everyone on the team. I blocked off an hour per person, and crammed ~20 hours of them into my first two weeks – along with a lightning trip from Buenos Aires to Philly for WordCamp US.

It was exhausting, but it was also illuminating. Change can be hard, and change in leadership can be especially scary – making that time for people, getting to know them and taking any questions they had of me – taught me a lot about what was going on in the team, and helped me be more successful.

Some of those first 1:1s were pretty dramatic. Lately they’ve not been as exciting, but that’s good. The goal isn’t just the meeting itself, the goal is to have a connection to people on the team, a more nuanced sense of what’s going on.

My standard set of questions are:

• How are you? Good to include life-specifics if there are any, e.g. “How was your vacation?”
• How are things on $team?
• How’s it going with $project? Mention recent achievements here if applicable, “I’m excited that X shipped!”
• Do you have any questions for me? If someone doesn’t have anything, I typically respond that it’s fine if they don’t have questions for our 1:1, if that means they ask me questions as they have them.
• Do you have any feedback for me? If there’s nothing, one thing I’ve been trying lately: “Do you have any advice for me?”

It turns out, you can totally fill an hour with these questions if they turn into a conversation (which hopefully they do) and they cover what I care about:

• How are they personally?
• How do they feel about their team?
• How do they feel about their work?
• Is there anything they’re wondering about?
• If there anything they want to change?

For managers it can feel weird that someone else is having a 1:1 with your directs. A tip I learned from my friend Julia Grace is to always sync with the manager ahead of time. Now we’ve done it a few times, it’s not a big deal for most people and I just give a general heads up, unless there’s something the manager and I are worried about, in which case we’ll sync up ahead of time and make sure we’re on the same page.

For scheduling, group teams together which is quite exhausting, but also makes it easier to see trends. Afterwards I’ll follow up with leads with any feedback or broader questions (e.g. if there seems to be a pattern). At first I found them a really important mechanism for getting managers feedback. Over time, we’ve developed different methods (e.g. feedback surveys, org surveys) and as the teams are running better that’s become less important. I generally think it’s a bad sign if I come away from a skip 1:1 with direct TODOs for that person, but sometimes people raise things that we discuss in the weekly leads call, or that I try and clarify for the entire team in an internal blog post.

I try to offer people a choice of format, unless say I just had tonsillitis and look like a reanimated corpse and then I might rule video out. At Automattic, we do a lot of 1:1s via text, which I actually really like. It might seem strange, but when people are used to it, you can have really good 1:1s via text, and I find it much less stressful than blocked off hours of back to back video or voice calls. I use Google calendar appointment slots to schedule, and if I know I’m going to be coworking or similar I mark them text only.

Skip 1:1s can feel really time consuming. I do them every other month, and I know on the months I have them it’s pretty stressful to block off all that time on my calendar. It’s easy to feel like you don’t have time to do them, but I’ve concluded that I don’t have time not to have a connection to everyone on my team, I don’t have time to only find things out when it’s a crisis, and I don’t have time not to hear people’s questions as close as possible to when they have them.

If you liked this, you might like my post On 1:1s.