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Thriving as a Remote-First Team

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    Ben Greenberg
  • Principal Consultant at Yalla, DevRel LLC

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It has now been several years since I began working for fully remote-first teams in software. My journey in a completely distributed team began before the pandemic arrived, and before countless numbers of people were thrust into this area unprepared.

Over the years I have observed several habits of remote-first teams that enable productivity, happiness and success. What I describe here is what has worked for me, and what I have seen work best in the places I’ve been. It does not mean that it is the only way. I encourage you to experiment and find the paths that fit your and your team.

Document Everything

A team separated by time and space needs to adopt one of the best practices of asynchronous work, which is to be over-sharers of information.

Whereas, teams that inhabit the same office space everyday can organize in-person meetings often and verbally share updates with each other, seek input and ideate on an idea, that is not possible for teams spanning time zones.

It may be possible to organize a meeting of all the team once in a while and ask people to work late in the evening or early in the morning within their timezones, but that is not sustainable long term. The answer is to become avid collaborators on team docs.

Use docs to deliberate async on a new project plan. Use docs to share updates from working groups. Use docs to figure out a bug that you just cannot resolve on your own. As much as possible lean into async written records. They not only allow for team work sustainably, but they also provide a phenomenal repository of information for new hires.

Share Your Wins and Losses

It can often feel a bit awkward to celebrate yourself publicly. Many of us were raised to not brag, and celebrating a success can very much feel like a brag. Yet, in a remote-first team, if you don’t share your win, no one else might know about it.

Why is it important that people know about your successes? There are numerous reasons:

  • Career advancement
  • Sense of accomplishment
  • Keeping everyone in the loop on progress
  • Building a culture of team celebration

Likewise, it is equally vital to share the moments that did not go well. Just as it can feel awkward to share your wins, it can also feel awkward to share your failures. Perhaps, it is embarrassing or you wonder what people will think about you after.

However, cultivating the sharing muscle, especially during moments of failure, is truly vital. Why? Because it normalizes the idea that we don’t always succeed, and builds a culture of learning in public within the team. This needs to happen in both in-person teams and remote-first teams, but because of the distributed nature of remote teams, we must be even more deliberate about it.

Trust Your Colleagues

It’s not a big surprise that one of the reasons supervisors love everyone working together in the same space is because it’s much easier to keep track of what people are doing all the time. From the earliest days of management theory, the notion was widely shared that if you weren’t watching employees, or if they thought you weren’t watching them, then it would just be havoc.

This couldn’t be farther from the truth.

People, by and large, want to do the right thing, and learning to trust your colleagues is a big leap forward. Within the context of a remote-first team it is imperative. Remote teams that implement all sorts of measures to track their employee productivity, in my experience, only adversely impact that productivity with each new measure introduced.

I’ve worked on teams where my manager was 7 or more hours behind me in the day. If they could not trust me and I could not trust them we would never have gotten anything done.

The cultivation of trust between colleagues on a remote team can be furthered with the next two ideas, which we’ll expand upon:

  • Check Assumptions (and Don’t Wait)
  • Intentional Meetings

Check Assumptions and Don't Wait

Do you feel like someone wronged you? Did someone totally drop the ball on a project or not reply to your request for help?

It’s easy to let those feelings grow and become a source of toxicity for you that continuously expands each passing day.

Remote-first teams don’t have many opportunities to serendipitously run into each other in hallways or by the coffee machine where grievances can be addressed. You need to deliberately seek the person out and check your assumptions about what transpired. It’s possible it was a misunderstanding. It’s also possible it wasn’t, and you both can pursue some reconciliation.

The longer you wait for the “right” moment to have the conversation the harder it will be for both of you. Finding a convenient time in the near future for both of you in a remote team allows both of you to move forward, and hopefully with relationships restored and issues resolved.

Intentional Meetings

They were the best of times. They were the worst of times.

While Charles Dickens may not have had corporate meetings in mind when composing those lines, they certainly fit.

Meetings can be incredibly useful to bring people together for a specific task and, in a short amount of time, accomplish something in real time. However, how many meetings have you attended or still regularly attend that match that ideal?

The best meetings that I’ve been a part of since joining remote-first teams have had agendas published in advance. They have had any “update” components of the meeting shared ahead of time so to maximize time for collaboration and minimize time for frontal presentations.

Meetings are one of the most expensive uses of a team’s time, if you think of all the collective hours of everyone there. Use those meetings well, and try to only have them when you need them. If a meeting is mostly updates, think about how that can be turned into a doc, or other consumable media form like videos, instead.

What You Did > The Hours You Worked

The best remote-first teams I’ve been a part of understand inherently that your contribution to the team is not measured in the number of hours worked, but rather in the quality of that work.

I strongly believe that it’s better to work to live, not live to work. I like finding meaning in my work, especially since I dedicate so much of my life to it, but it’s not the sole driver of that meaning. One of the greatest benefits for me of remote-first work is that I get to fit work into my life, and not my life into my work.

Dentist appointment for a kid? I can gladly and happily take that responsibility without feeling pangs of work guilt.

Time to read in the middle of the day or go for a walk? Yes, absolutely.

In the same way that I trust my colleagues, I trust myself to do my best work in the way that is most genuine to me. A remote-first team that starts asking for daily clocking in and clocking out is presenting a large warning sign about its health.

Those are some of the habits and practices that I’ve observed in the remote-first teams where I’ve had the most joy and success working. Overall, there is a culture of sharing, of trust, and of respectful candor.

What ideas have you seen work really well in remote-first teams?