Leading in Pyjamas

I had a great day at the Lead Developer Austin conference last week. All of the talks were high quality and being at conference focused on leadership was energising. I also absolutely love the Austin library. The conference gave me the chance to meet with some remote colleagues and have some in person conversations. This made Katie Womersley talk about Buffer’s remote culture strike a chord. Remote work is part of Auth0’s DNA and it’s something we/I think about all the time. And, it seems we do have a lot in common with Buffer and I took away some things to try out! (I’m a tools nerd, so I love seeing what other people are using - in the same way I love seeing how people setup their dev boxes).

Auth0 recently published an interesting blog with quotes from our distributed workforce. In it you can see patterns clustering around flexibility. Whether that be flexibility to be with your family when they need you or to work from anywhere in the world. (Do a search for “dog” and you we have some global common ground).

When I was an IC there is no doubt working remotely was hugely productive. I also took advantage of travelling and being able to work from anywhere. But what about leading remotely?

I don’t lead from my pyjamas or even wear pyjamas but I do in an Auth0 t-shirt often - which I imagine makes it look like I do. I’m a huge fan of managing remotely; the people we are able to hire and the flexibility we can give them makes it worth it alone. So with that context, I wanted to explore some areas to think about and that we can improve on.

A maker versus a managers schedule can be very different. A managers schedule can translate to a lot of meetings and if you’re remote this means video conferences (or as to me to vacuum is to hoover, to video conference is now to Zoom). This was also described to me last week as “I spent 8 hours a day sitting on my a**”. Video conferencing requires a different set of skills than you would use in an meeting room. It’s just much harder to read people and see where the energy is in the discussion. In the same way presenting on a VC takes practice (speaking into the void) so does conducting meetings via this medium. Beyond practice, if you’re part of the group in the conference room you can model good behaviours by being keep conversation flowing out to the people who are dialled in.

The medium that you deliver your message is very important in a distributed team and if your primary communications channel is Instant Messaging then the temptation will be to always default to that. One of my first, recent and continued learnings is: don’t discuss anything you think may be contentious in IM (ok you win Slack, in Slack). Even if to you it seems completely uncontentious people read it with their own state at that time and being asynchronous you may not be there to correct their interpretation. In Katie’s presentation the point: “don’t making decisions in Slack” is something I strongly agree with. Slack feels like and anti pattern for discussion and for recording the outcomes. And it’s also not a good medium for conveying your true meaning.

Feedback can also suffer when leading remotely, particularly instant feedback that is so effective i.e the “that was good as you walk out of a meeting room”, or the “let’s have a quick coffee because we need to correct this”. You connect at meeting time and then you literally hit a button to disconnect from each other. This doesn’t have to be lost in remote work but it needs discipline; asking someone to jump on a VC straight after a meeting (do this a few minutes before the meetings ends as people tend to run off to make tea). Reworking your schedule a little on the fly to re-prioritise those discussions when you have a build up of back to back meetings is important. If you have received an “omw” Slack from me I am likely doing this - or running out to get tea.

Tech companies like to build autonomous teams - these are the teams I like working in and the teams I like building. And, no surprises, these are the most successful distributed teams too. Smaller autonomous teams working together with a great manager - it’s here where managers can really shine by being the glue that keeps their remote nodes together. The challenge here for a senior leader is that you may be well connected with your directs but there is not natural point where you will connect with the team as a whole - such as at the coffee point - unless you create one. Be that a skip level 1:1 or a regular team meeting.

Often what you are pushing against is isolation. Isolation of team members who are not working on a collaborative task or who are a different timezone. Or isolation of yourself from your reports as your focus is drawn to something urgent or strategic. This is where discussions about mental health are so important - acknowledging the side effects of possible isolation and making a space for people to talk about how it impacts them. I instinctively push back when someone saying: “I know your busy, but…”, the connection always needs to be there even if it’s in a DM that’s answered a few hours later.

This is a quick, unstructured post about leading remotely totally inspired by the great talks and conversations last week. Hopefully it will turn into a talk of my own.


Duncan Godfrey

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