Now, let’s talk about how to run a team from anywhere. Over the decades, countless books have been written on how to manage a team and be a great boss. Most of these books assume that the team is all together in the same location, which is clearly not the case these days.
In this chapter, I’m going to share specific tips and tactics when leading a distributed team. My hope is that you won’t find generic “here’s how you can be a good boss” advice in this chapter. We’ll leave that stuff for the other books written 30 years ago.
The first thing to consider is, “what makes leading a distributed team so difficult by default?”
I’d challenge the notion that it’s tougher to lead when remote, but instead, that the tools you used in the office don’t work as well now. It’s like a carpenter using a hammer when they should be using a screwdriver instead. It’s not that one tool is better than the other. It’s that each tool serves a different purpose.
With that being said, leading a distributed team is not a walk in the park. Here are some challenges you will experience:
As I mentioned in the beginning of the book, the office provides a natural collision space for observing what’s going on. You can use the office to “manage by walking around.” As the name suggests, this activity is when you waltz around the office and talk to people. It gives you a chance to observe, nudge, and understand what’s taking place. This activity gives you steady stream of data to improve your effectiveness.
When everyone isn’t in the same room, you can’t walk around and see what’s going on. You may feel like you are flying blind. It’s natural for leaders to try to replicate this office activity online by randomly pinging coworkers in workplace chat (management by chatting around), which can be annoying and distracting.
A hallmark trait of a great leader (at least the stereotype) is the ability to persuade and influence. Often this means you are great at talking in front of a group of people and can energize the room. When remote, you are much less persuasive because of the following reasons:
Next up, it can be difficult to understand how someone on your team is feeling. When a team member walks into the office, you can often tell by the look on their face. As a leader, when you see that someone isn’t feeling so well, you can intervene and try to help.
When remote, it takes much longer to discover that something is wrong, which means that it can take more time to resolve these potential problems.
Leaders will rarely admit that they manage through “butts in seat,” but it is easy to conflate activity with output. When remote, you can look at a workplace chat tool to see if people are online and equate this to “sitting at the desk, doing work.” It can be easy to unintentionally grade people based on how quickly they reply to your messages and pings, even if that is not your intent.
Another reason why it’s so difficult to lead a team when remote is that people become sick of the endless meetings. As a leader, meetings are a tool in your toolbox to create alignment, the feeling of connection, and to understand what’s going on. But what happens if everyone is complaining about Zoom fatigue? Do you want to compound the issue even more?
If we look at the problems above, the root cause of remote management woes is that there’s not enough data being exchanged between employees and leaders. The only way to fix this is by creating ways to speed up the flow of information between you and your team, but in a way that doesn’t add another meeting or more distractions.
The most important tip I have for leaders is to run a regular, asynchronous check-in. Every week (or two), ask your direct reports the following questions:
This is like a weekly update, but instead of being public and viewed by the entire team, it’s only accessible to the employee and leader. This pulse check helps you understand how people are feeling about their week and also helps you kickstart more effective 1:1 meetings.
There’s a few reasons why I recommend this approach:
The insight from this routine will help you proactively identify potential problems and also help you discover ways to personalize someone’s work experience. The output from this asynchronous routine is very similar to what you might learn in the first twenty minutes of a 1:1 meeting.
The second most important tool in your managerial toolbox is to have dedicated 1:1 conversations to get to know each person on your team. One of the most common examples is a 1:1 meeting.
I don’t have regularly scheduled 1:1 meetings on my calendar. I will create on-demand 1:1s based on the feedback that I receive in the asynchronous check-in (see previous tip). Then, when I chat with someone, I try to spend extra time chatting with them as people instead of feeling pressure to check in on the status of a project.
If someone is struggling with work, I will find out through the check-in and will schedule a 1:1 meeting based on that. I find this process more effective as there are rarely awkward conversations. You always have something to talk about!
This next tip applies to co-located teams, too; but as a leader, you need to create clarity of expectations and write them down. We discussed this idea in the chapter on hiring, but the premise is that you need role and goal clarity:
I’d strongly encourage you to dedicate time to collectively hang out as a team and do something besides work. We discussed this idea more in the chapter on how to feel connected.
For example, someone I know would hold Friday afternoon “happy hours” with his team. As the name suggests, the team would jump on a Zoom call early on a Friday afternoon and chat. While there would be a little bit of work discussion, the entire point of the call was to hang out. Many leaders have tried to do this throughout the pandemic, but often run into implementation problems, like:
It’s easy for leaders to unintentionally hoard information. You may chat 1:1 with one person about a topic or goal and then have another conversation with someone else on your team. These discussions don’t travel across the team, which means that the information is trapped and you are the only source. Congratulations, you are now a bottleneck!
Instead, you need to remove yourself as the bottleneck. The only way to do this is by documenting a conversation asynchronously and sharing the takeaways with the broader group.
Speaking of communication, one area you will need to pay particular attention to is creating and enforcing communication norms. You are the communication architect for your team or company.
You don’t need to go overboard, but gentle nudges and modeling the expected behavior goes a long way. For example, if you see a long discussion happening in Slack without a lot of progress being made, consider proposing that people jump on a video call instead.
If people are discussing something in a meeting that should be shared more broadly with the rest of the group, consider asking someone to take notes or record the Zoom call.
Another pro-tip for leading a distributed team is to avoid giving negative feedback asynchronously. If you need to deliver bad news or feedback that could be interpreted in a variety of ways, make sure to do this in person, over a Zoom call, or on the phone.
At one of my first remote jobs, my boss delivered negative feedback to me over an email. I’m sure the intent was to be helpful, but it was scathing. I’m confident that if he shared the feedback over a video call, I would have interpreted it differently. Written messages can be interpreted in many ways, so you need to tap into the fast feedback loop that a real-time conversation enables.
Side note — if a software vendor offers the ability to share performance feedback through software, you should run the other way. It’s a terrible practice that will cause issues at some point.
To wrap up this chapter, effectively managing a distributed team is not too different from the best practices you’ve seen in management books written decades ago. The major differences are that you need to over-index on building relationships and to act like a communication architect to make sure information flows where it should.
Want to keep going? Read the next chapter where we discuss hybrid work.