Leading a team at WordPress.com is a great opportunity – I wrote about my approach this a little bit before – we’re a fully distributed company, and we’re always able to switch things up, iterate on our work as well as our meta-work, the labor that enables us to work at our best.

One of the tools in my toolbox as a Team Lead is the one on one. I sincerely believe that regular one on ones are absolutely essential to maintaining a cohesive team that gets along, and performs. I’m happy to say that I am in good company on this position.

This Post is meant to be a record of how I’m conducting my one on one sessions today – this is bound to change in the future as I learn more, and as my team shifts around. For now, this is the best way I’ve found to approach them. This Post is about the structure of my one on ones – not about the actual conversations themselves.

For a new hire, I generally ask to do one-on-ones every week, for at least the first few months of their employment. This is mostly because there are so many things happening and changing that waiting more than a week between catch-up sessions means a lot slips through the cracks.

That first little chunk of time with the company is so vital to a long and happy relationship, making time for and closely attending to those early one on ones is something I really try to prioritize. I want to make new employees feel welcome and supported. Also, a little, safe and powerful.

If someone is new to my team but has been with the company for a while, I’m happy to skip this early phase and jump right to the next part.

Once someone is comfortable in their position and seems able to wrangle their day to day without much fuss, if they seem to chafe a bit at the weekly frequency, we can bump it to bi-weekly – but I have a serious inclination toward keeping the one on one weekly.

A week doesn’t seem like a long time, but it’s not so much about the length of time as it is the relative closeness to recent events – something that happened ten days ago, even if it was moderately important at the time, may not seem of any import at all today. And that might mean that something important gets missed in our chat – maybe a nagging problem with a colleague, maybe a tiny but brilliant change in the way you do work – these things are important for me to hear, so I can help you solve problems before they become problems, or so I can help you amplify your new ideas across the team and company, which can help you become a force multiplier.

Keeping the one 0n ones to relatively frequently offers another advantage: they don’t have to be too long. I aim for around 30 minutes, although they do sometimes go longer for various reasons.

Organizing the one on ones is fairly simple – we pick a start time each week, and plan to meet at that time. I try to be flexible with these – if folks are sick or busy or whatnot, we can shift things around. The important part is getting the time in.

I create a shared Simplenote document for each member of my team, and we use that to set an agenda – throughout the week I’ll add items I’d like to touch base on, and each person adds items to their own as well – I’ve recently reduced the duration of our one-on-ones from an hour to closer to 30 minutes, in the interest of respecting everyone’s time. I’m not totally sure that’s enough time, given that I like to do some social chatting during one on ones rather than being all business – but we’ll see. We can always change it later.

One thing I am a stickler on is using voice chat – for a one on one, I think text is really a poor medium. We use Slack for most of our synchronous communication at Automattic, and it has a lot of upsides, but I find it tremendously distracting, and I think it’s must easier for both parties to lose focus during a text chat.

Text chat, even with colleagues you know and are generally simpatico with, can hold a lot of space for misunderstandings and misinterpretations. “I’m doing fine,” can have a broad array of meanings. A pause in conversation could mean anything: are they thinking? Are they playing Hearthstone? Are they complaining about the one on one in a back channel?

Doing voice, we tend to cover more ground, in less time, with fewer interruptions. It also helps me know which of my jokes are falling flat (spoiler alert: most of them). I very strongly prefer voice for most one on one communications, roadmapping, really anything that has any sort of professional or career heft to it, I prefer voice if at all possible.

There’s quite a lot more to say on this subject: when it’s OK to take a pass on one on ones (almost never), how to conduct the one on ones conversations (trial and error), and what makes remote leadership different from in-person leadership (everything). Those are posts for another day.

Do you do one on ones with your team? Do you think they’re useful?

 

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