I’m working on a massive opus of my thinking on one on ones, how important they are to remote teams, and a bunch of tall tales about the times I’ve messed them up, and how to avoid my mess ups in your own life.

(Note: This massive opus will not be a list of questions to ask during one on ones. We have enough of those 🙂 )

If I were writing for an actual publication and not my personal blog, it would have an SEO optimized, click-gravity headline: “The Ultimate Guide to Remote One on Ones” – “You Won’t Believe What This Dude Said in a Remote One on One!” – “56 Ways to WOW your Boss!” etc etc.

( You can see my first ever post about one on ones here: Communicating with a Remote Team: One on Ones)

One thing that doesn’t fit super well into that piece, but is still something I want to talk about, is that one on ones are important, and they are hard to get right.

Many folks who are leading teams (remote or otherwise) walk through one on one sessions without much order or preparation. Once the calendar item pings, they dive in. No prior preparation, maybe they have some notes from the previous week, but by and large the one on one session is flying blind.

“So, remind me, what are you working on right now?”

If you have to ask that question, as a team lead, you’re not doing your job. It’s your job to come into every one on one prepared, and not just with an understanding of what your team is working on but why.

It’s your job to lift these people up. It’s your job to insulate them from all of the turbulence that cannot help them, and to really dig into the why of each individual. Knowing what they are doing is good – knowing why it’s important to them and their career is great.

The reason the why is important is because it can vary widely across individuals – maybe someone on your team cares deeply about democratizing the web, so issues like accessibility and internationalization are what drive their desire to provide support. Maybe someone else on your team actually wants to step into a front end development role, and support is a great first way to understand a product deeply.

While both of these individuals are doing the same tasks day to day, your understanding of their deeper why allows you to better help them find ways to leverage that work toward their personal goals. Helping the first person become a Github guru might miss the mark; similarly, the second individual would be confused if you invited her to attend a translation summit conference.

It’s not always that easy – not everyone has grand career aspirations, or at least not ones that they have a great way of sharing with their team lead. Not everyone is motivated or compelled by work. Not everyone has an ambition beyond where they are today – that’s OK!

As a lead it is on you to know who is who, and to know on some level what drives them, or that they are not driven to pursue greater things at work – at least not today. That’s the real trick of it, is that just because someone is leaning out of work this week does not mean they won’t become someone with different goals in two, three months.

It’s a lot to keep track of, and if you allocate 30 minutes to your 30 minute one on one sessions, you’re missing out on a lot of value you could be offering your team members.

I like to do half hour one on ones weekly with my team. I would love to do video every time, but I am willing to settle for voice, and will do text from time to time (reluctantly). I spend about thirty minutes that day also preparing for each one on one session.

That’s not thirty minutes total. I spend as long preparing for the one on one as I do having the one on one. If I have four 30 minute one on ones, that takes me about four hours.

(You can read about how my approach to one on ones has changed over time here: Experimenting with One on Ones: Tales of a Team Lead)

I am a compulsive calendar junkie: if something isn’t on my calendar it generally does not get done. Here’s a visual:

(Thursday is so empty because this Thursday through Sunday the Doc and I are having a lovely long weekend bonding with Mango.)

The natural next question is, what do I do with these 30 minutes?

I am very lucky in that at Automattic, we have a real culture of transparency, and default to over communicating rather than the opposite. I am working on having a better 30 minute structure, but right now, I do this:

Check the team member’s last Weekly Update, which is a structured post we do on Mondays. Follow those trails a bit – look into projects and work they mentioned.

Check their trac and Github contributions over the last week

Scroll through their P2 (our internal communication tool) activity, to see where they’re having an impact and hopefully catch them doing something right.

Review our shared, running notes from our one on one sessions

Consider how I can help move them toward their goals, what advice or direction I can offer. Look for roadblocks.

If there’s time: look through their last 3-2-1-Oh document

In a non-remote environment, it might be trickier, and it might take even more time, since you wouldn’t have the advantage of being one click away from these various records. You’d have to check in with folks on other teams, go back through emails, etc etc.

(You can read about why I don’t use one on ones for status updates here: Iterating on One on Ones)

At the end of the preparation time, I aim to have:

A handle on how their week looks from my end

Suggestions on how to move toward their goals over the next week

Questions for feedback (in both ways, “How did your rotation with Terms of Service go?” but also, “How do you think I handled that situation?”)

If I were to dedicate only the time during my day for the one on one itself, it would be very difficult for me to really serve my team in the best way that I can. Not to say it would be impossible – but you’d need a much better memory than me, at least 🙂

If you lead a team, for the next week or two weeks, try spending more time really focused on preparing for those conversations, and coming to the table not with canned Applebee’s interview questions (“What would you say you’re struggling with?”) but with insights into their actual work, and how you can help make that work easier, better, or just more fun.