Developing a Process for Better 1 on 1’s

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As a team lead at Automattic, I have a weekly one on one meeting with everyone on my team. We’re a small team (seven total people), but it’s the top priority in my week. After all, my main responsibility is to help the team function better. A natural first step is to meet with those individuals on a regular basis and ask things like “How can I best help you?”

Initially, the chats had very little structure. As the team was first getting started, I setup 30 minute slots with everyone, and we just talked (mostly work, but anything really). Through much trial and error and after learning from colleagues, the process has evolved. Here are some of the approaches that have had the biggest impact.

Preparing ahead of time

This seems pretty obvious. If you’re taking up 30 minutes to an hour of someone’s week, it better be valuable. Previously though, “preparing” took a very loose form. Now, it’s very structured. The whole process takes roughly 20 minutes.

Since I work Sunday through Thursday (currently), I prep for all chats on Sunday. The prep work includes three steps.

  1. The first step is to review notes from our previous conversation (all stored in a Google Sheet—more on that later). I start making a list of topics I’d like to discuss.
  2. With a tentative list in hand, I review work from the previous week. For a Happiness Engineer, that includes things like ticket/chat work, bug reports, p2 posts, GitHub issues, etc. That information is added to the Google Spreadsheet hinted at above.
  3. At this point, I have a pretty good idea of things I would like to chat about. I compile that list and send it to the individual in Slack as a rough agenda asking if they have anything they would like to add. I just recently started this (previously, I would introduce the proposed agenda at the start of the chat), but I’ve already seen a noticeable impact. This makes sure we’re both on the same page and gives both parties time to think about any of the specific agenda items ahead of time.

Focusing on the conversation at hand

This is spectacularly important and surprisingly difficult. Since we all work remotely, there’s a chance that these one on ones are happening through Slack. In that case, there’s always the temptation to do other things while waiting for the other person to respond. If we were having these face to face though, there’s no way I would be checking email during a one on one conversation.

Breaking this habit was extremely tough (I still fall prey to it occasionally). Two things have helped:

  1. Voice whenever possible. It’s great to catch up with someone over video. You can discuss the same amount of info in a much shorter time compared to test. It also has the added benefit of requiring all of your attention.
  2. Put away your mouse. I move my mouse off of the desk so I can’t easily change from one screen to the other during a conversation. For the most part, I’m stuck with the window I’m on (usually Slack).

Ending with the same question

I try to always end my one on ones with the same question, which is borrowed from Jason Evanish:

What can I be accountable to you for the next time we talk?

I don’t always get an actionable item, but I’ve found that continually asking the same question gets people thinking. They may not have something for you the first three to four times, but it sets the right mindset. These one on ones aren’t just about me holding you responsible. It’s a two-way street. I need you to hold me accountable as well.

Keeping a record

Above under preparation, I hinted at a Google Sheet for tracking one on one conversations. Every person on the team (including myself) has a Google Sheet that contains three separate spreadsheets—a volume chart (tracking tickets, chats, p2 posts, GitHub issues, etc), a volume graph (easier to spot trends), and a 1-1 tracking sheet. The sheet is only accessible to myself and the team member.

After every one on one, I go back and fill out the various columns. There are four important ones to note:

  • Personal (for anything awesome or interesting going on that I want to make sure I remember — trips, birthdays, apartment moves, etc).
  • A “What can I hold you accountable for?” column, which tracks specific actions we agreed upon and reiterated through text that we’ll follow up on next week.
  • A “What can I be accountable for?” tab which tracks the answer to the question above.
  • General notes, which tracks our agenda and anything of note for each item.

The tracking piece has two important benefits. First, past trends become more obvious. If I’m writing down the same thing for what I can be accountable for, I’m falling short somewhere. Second, the conversations become more progressive. We can build from one week to the next.


The one on ones are still a work in progress, but they’ve come a long way from the “What’d ya wanna talk about?” nature at the beginning. If you have any specific tactics that work, I would love to hear about them!

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