Transitioning to remote work: What to know and do before becoming a remote leader

Recently, I was asked, “Claire, what advice do you have for a leader who’s transitioning to a remote team?”

I had to think about that question for a while. After all, it’s been a while since I’ve personally transitioned from running a remote team – I’ve run Know Your Team as a remote company for the past five years.

However, in posing the question to our 1,000+ members in the Watercooler in Know Your Teamand pulling data from the survey we conducted amongst almost 300 remote managers and employees, there were definitely key themes of “There are things you should definitely know about before making the leap to managing a remote team.”

Whether you’ve been assigned to a new remote team, are joining a remote company, or have some new remote direct reports joining your team, here are the most pressing things to keep in mind and pitfalls to avoid as you transition to becoming a remote leader…

Commit, don’t dip a toe in.

You can’t half-ass running a remote team. I’ve noticed this in watching other CEOs try to transition their team into becoming a remote team… They only let a select few people work remotely, or they don’t make writing things up a priority, or they don’t make what’s going on in the company accessible to their remote team members. That doesn’t cut it. The remote folks get treated like second-class citizens. Over at Help Scout, their CEO Nick Francis says exactly this when talking about their remote culture of 60+ employees world-wide:

“A friend and investor in our company, David Cancel, once told me that you have to choose remote culture or office culture and stick to it, because there is no in between… Trying to optimize for both will likely result in remote employees feeling like second-class citizens.”

Similarly, Help Scout’s Head of People Ops, Becca Van Nederynen, shared that, “You can’t dip your toe into remote work, it requires 100% commitment.”

At Know Your Team, we live this maxim daily. Even though Daniel, my business partner, and I are both located in San Francisco, we communicate with one another as though we don’t live in the same city: We talk via chat and Zoom for a majority of our communication. That way our other team members who are not in San Francisco aren’t left out of the loop.

If you feel you can’t be as “all in” as you’d like as a remote manager (for example, your team is composed of a mixture of both remote and in-person employees), consider a “if one person is remote everyone is remote” rule for meeting. One Watercooler member mentioned this, writing: “If all the people in the meeting are at the same office, sure, go ahead, take a room to talk. If even one person is somewhere else, open a conference call, and everyone grab their headset and join. Don’t have everyone in a room and just the one poor guy or gal on the call. This helps everyone feel the remote pain (if any), and make the meeting go on an equal footing. I was a bit hard to start, but it pushed us in making a lot of progress quickly.”

Focus on setting up basic processes and tools immediately.

“If your team today relies heavily on meetings and interrupting each other to get stuff done,” one Watercooler member wrote, “Switching to remote will be a nightmare.” As a result, it’s paramount to initially focus on setting up some foundational processes, guidelines, and tooling so your team doesn’t feel lost.

For example: If somebody has a question, do people know where to ask? Does your team think they need to be watching Slack all day long to stay up-to-date? If someone completes a task, do they know where to go to find new work to do? How do people communicate their progress with each other and outside their teams? How can ideas turn into projects, and where can people see that happening?

For more best practices on how to set up processes in a remote team as a manager, be sure to read Chapter 3.

Keep in mind that takes time to get to the right process. You’ll likely have to change, adjust, change, and adjust again as your team and your company grows and shrinks over time. However, formalizing these processes give you and your team the foundation to figure out what will work in the first place.

Consider too, that you want these processes to not be a burden. Your team shouldn’t have to rack their brains trying to memorize them, and they shouldn’t have to be checking a document on “How to work” constantly (and they definitely should not be penalized in any way for not following them).

At the end of the day, these processes are iterative. Together, you’ll figure out what works best.

Over-communicate almost everything.

As discussed in Chapter 2, communication is only made more important in a remote team, when you can’t see each other face-to-face. This means that it’s your job as the leader to set the example and communicate often and clearly to set the tone in the team. How is the team communicating what’s going on? How is the team communicating decisions? How is the team communicating challenges and big wins? How is the team communicating gratitude? Reflect on how you’re creating opportunities, systems, and channels where folks can both receive and participate in these communications.

This extends in particular to communicating work hours and work progress. The best remote teams tend to constantly communicate what they are doing, where they are, when they will stop working, when they are online and available, etc. That sets the right expectations and makes things much smoother.

If you are switching to being a remote manager, one Watercooler member suggested “a small cheat-sheet with remote communication best practices with things like:

  • If you are going to be offline to take care of some personal things during the day, please notify your direct team on their Slack channel
  • If you are planning to work at odd hours schedule for a few days please let everybody know up-front.”

Emphasize training and onboarding — especially for junior employees.

When you’re new to a remote team, you’re in for a challenge. That’s why it’s important to invest in onboarding and training new hires well. You can read more about onboarding remote employees well in Chapter 7. You may also need to prepare for the fact that for new junior employees in particular, there may be more of a ramp up period that’s greater than in-person. Wrote one Watercooler member, who reflected on his experience: “In my experience, it’s much harder to coach an intern or a junior person that needs a lot of guidance in a remote environment than in-person. I never actually had a good experience, but it might be possible with today’s technologies. But I think this is something that you have to be aware and plan for.”

Focus on building trust.

According to our survey, what most managers overlook is building trust and fostering rapport in their team (25% of people said this). It’s easy to, given all the other things you feel like you might need to get in place first (e.g., communication processes, tools, etc.). And it can also feel non-obvious of exactly how. Set up some standard means of building trust. This can be via video chats that you schedule to talk about something fun once a month or establishing a non-work-related specific chat channel. Whatever it may be, being intentional as a leader and putting focus toward building trust will help you avoid being one of the remote managers who think to themselves, “Oh man, I really should have paid more attention to how we build trust in the team.”

To get a full sense of what exact ways you can build trust as a remote leader, be sure to read Chapter 4.

Not everyone likes to be remote – be ready to adjust accordingly.

It’s easy to assume that when you become a remote manager that everyone will enjoy working remotely. This is not the case at all. As one Watercooler member remarked: “One of my favorite people to work with doesn’t like being remote. He likes being surrounded by people, going out for lunch with the team on a daily basis, etc.” So, how do you account for this? The Watercoolor member suggested: “You can try to address that by having off sites/gatherings a few times a year, having remote social sessions (like a happy hour via hangout) and cover coworking space.” And yet even with those mechanisms in place, some people still might not enjoy being remote – and so it’s important to be cognizant of this. Be sure to ask questions actively in one-on-one meetings to find out if the environment is working for them… and if not, what exactly you can do.

If you’re making the switch, explain why are you going remote.

Oftentimes, as a new remote manager, your company is making the switch to becoming remote – and it confuses the hell out of people. Your team then makes assumptions about why certain folks are remote, but not others, or don’t understand the reasoning behind the move in the first place. The result is some of the team feeling like “second-class citizens”… and eventually the parts of the company that are remote versus non-remote actually can develop different cultures. The latter is actually not necessarily a bad thing, but sometimes is an unintentional and negative by-product of the fact that you haven’t made the reasoning behind the move to remote work clear. Don’t assume everyone knows. Your smooth transition as a remote manager depends on it.

Naturally, these suggestions don’t cover every single scenario, nor will they all apply to your exact specific situation. Though, as you make this transition, consider trying at least a few – especially establishing processes and building trust. The effort will make a difference in your transition.

Takeaways:

  • If you’re thinking about going remote, commit – don’t dip a toe in.
  • Focus on setting up basic processes and tools immediately.
  • Over-communicate almost everything.
  • Emphasize training and onboarding — especially for junior employees.
  • Focus on building trust.
  • Not everyone likes to be remote – be ready to adjust accordingly.
  • If you’re making the switch, explain why are you going remote.

Put this into practice with Know Your Team:

  • Know Your Team can help you make the transition to a remote team: You can get feedback with our Culture Questions, ask fun Social Questions, and get updated on what everyone is working by way of our Heartbeats – all without disrupting them via chat or calling an all-team meeting.