My Remote Leadership Best Practices

Below is a slightly modified version of an email I sent to a peer group as covid set in. Their companies had become "remote" overnight, and they were looking for insights. I also shared this recently with our leadership team as a reminder of my personal best practices for leading distributed teams. I hope you enjoy it!

Slack is worse email, do not use it for more than one-off communication.

If you are not already heavily invested in Slack as a platform, stop right now. I strongly suggest you take Twist or Basecamp for a test drive. Both are much better at respecting the audience receiving the communication, versus Slack, which focuses solely on the sender. People in distributed teams need to triage and respond on their own time; Slack makes everything urgent.

You are going to lose watercooler chat unless you invest in new cultural norms.

Watercooler chat is an accident of working in proximity to one another. If your company thrives on creativity and the magic of serendipity to succeed, you need to create virtual proximity. Take a lesson from MMORPG players and use a voice chat system that allows people to passively communicate throughout the day without the ceremony of scheduling a meeting. You have a lot of options here. I would recommend Discord as it will eliminate Slack. However, if you are looking for a voice-only solution, Mumble, TeamSpeak, or Ventrilo are proven alternatives. The tools like these allow people to speak their questions aloud and have others overhear, just like you would in an office. There is no doubt a generational gap to this approach, but I can tell you teams that work this way are much more connected and collaborative.

Timezones are irrelevant

Most leaders take the shortcut of assuming people work 9-5 and therefore look across their team and see how timezones align to form core hours. Do not do this. Distributed teams do not conform to 9-5. Instead, ask your team what their anticipated hours are. Then, work together to understand when there is overlap and, more importantly, how you all want to use that overlap. The overlap is when collaboration is most likely to happen; do you need a thirty-minute standup taking away from that? What about that weekly status meeting or that biweekly retrospective. There is so much waste in colocated companies that goes unnoticed. You have to question all of these when you are working in a distributed team. What can become a document, a blog post, a forum post, a slack message, or a Discord rant? Ask—and answer—that question with the team, and you will be on your way to successful collaboration.

Lean on OSS contributors for best practices.

Very likely, you have a few developers who contribute their time and talent to open source projects. These folks are a goldmine for distributed work best practices. By necessity, nearly all OSS work is distributed and asynchronous. Take time to understand how these projects run and apply their lessons to your teams.

Do not be an asshole and assume anything about someone else's calendar.

In meatspace, you can "manage by walking around"—also known as "interrupt an individual's flow at will"—without much backlash. Many managers do this in a distributed environment by scheduling meetings with their team members and deciding when they can ignore what is on someone's calendar and overwrite it. Do not be this asshole. If you cannot find the time for the team to meet or an individual, ask them to help solve the problem. Hopefully, you already ask them to solve the problem instead of finding the solution on their behalf. By doing this, you are signaling their time is essential, and you are a legit servant leader—though, still, I am not too fond of that phrase myself.

You need a documentation source of truth—though no one will use it.

You will need a wiki—Basecamp, Notion, or Confluence—to organize your "digital artifacts." It will make everyone feel better. The team will barely use it. However, it will help reduce the discussions around where to keep the information, enhance onboarding new employees, and provide real value when an emergency happens.

Finally, learn to trust and respect your employees.

Tell yourself this before adding new policies to prevent hypothetical situations. These people are smart, professional, and likely highly paid. Do not burden them with unnecessary red tape because you are afraid—it is time to become a real leader. ;-)