Over the last couple of weeks, a few people reached out to me for advice on how to help their teams embrace remote work. During Covid, this topic became a hit, and I gave a bunch of talks sharing my experience building a distributed startup. But it’s been a while since I talked about it. It seems that, despite the big shift to remote work, many teams are still struggling to do so effectively.
I think the hardest mental shift people need to make to thrive in a remote environment is learning to work async. By default, most teams try to replicate the sync rituals from an office in a remote setup, and that doesn’t work very well. You easily end up with a calendar full of meetings, and productivity plummets. The office had its problems, but at least people could tap you on the shoulder and move on. On a screen, every interaction becomes a scheduled call.
Matt Mullenweg wrote a great piece back in 2020 called Distributed Work’s Five Levels of Autonomy, where he describes how most companies that went remote during Covid got stuck at Level 2: they accepted that work would happen from home, but they just recreated the office on Zoom. Everything remained synchronous; no meetings were canceled, and management began worrying about productivity rather than focusing on outcomes. The real shift happens at Level 3 and beyond, when async processes start replacing meetings and written communication becomes the backbone of how work gets done.
After almost five years of working at Automattic, one of the largest and longest-running distributed companies in the world, I still find it useful to revisit our internal expectations from time to time. In fact, one of my favorite Automattic pages is the public Expectations page. It’s a very practical guide on how a team can thrive in a distributed environment. Things like communicating often and publicly, being accountable, getting context before asking questions, and never missing a ping. It sounds simple, but turning these into habits is what separates teams that make remote work look easy from those that are constantly frustrated by it.
If you’re leading a remote team and things feel harder than they should, I’d start with those two resources. They won’t solve everything, but they’ll help you identify where the friction is coming from. In my experience, it almost always comes back to the same thing: too much sync, not enough trust.
If you work on a remote team, I invite you to try something simple: find one recurring meeting where most of what happens is people sharing updates in one direction. One person, or several, just reading out information that could have been written down. The famous “this meeting could have been an email.” Please try replacing it with an async update, and use the sync time you free up to discuss the information that was previously shared. You’ll be surprised how much more productive those conversations become when everyone has already had time to read and think.