Setting Employees Up for Success in a Remote Environment

A team member of yours is about to become remote for the first time.

Or, you’ve just taken over for a team with a few folks who are going remote for the first time.

You’re wondering: How do I set up my team for success in a remote environment?

You want your employees to feel prepared, confident, and ready to execute. Here are six things you can do to make sure they start off on the right foot.

Let people know that remote work is different – there is a learning curve.

You don’t just start naturally doing remote work and become good at it. There are specific habits and skills you have to pick up. And that takes time. These expectations are important to calibrate because many assume remote work is just doing the thing: You work and you’re no longer in the office. Warn them that it might feel weird to not have a clear “start” and “end” to their day, or in-person watercooler chit-chat with their co-workers. Let them know that if things do start to feel “off” to mention it to you. Establishing a steep learning curve as the norm, not the exception, will help your team members who are new to remote work not feel discouraged in the beginning – and for them to internalize that with entering a new system of work, they’ll need to adapt and adopt a new system of work.

Raise flags where pitfalls are, so they avoid stepping in them.

If folks aren’t careful, it’s easy to fall subject to the pitfalls of remote work. Here are the key ones to make clear to your team:

  • Overworking is easy if you don’t have a clear end point to your day, or find yourself continuing to check email incessantly over weekend.
  • Loneliness can become a real issue if you’re not cognizant of your own needs to connect with your team members.
  • Miscommunication can be rampant if it’s not made clear how much empathy plays a role into not taking a particular chat personally, or if someone doesn’t know the systems of written communication.
  • A lack of deep work / constant interruption can occur if the person doesn’t absorb the communication processes that you’ve set up as a manager. You can read more about the specific communication best practices for remote teams in Chapter 2.

Coach them on what to lean into.

In addition to things you want your team you avoid, there are things as a manager that you want your team to lean into more. Particularly:

  • Over-communication rarely feels like over-communication. The more you both proactively share progress, the more you can make sure you’re both on the same page. This way, small problems will get resolved sooner and won’t bubble up into something bigger.
  • Lead with empathy. Not sure what someone meant by their note? Assume positive intent. Feeling bothered with the way someone communicated their request? Kindly share the feedback of what you observed and how you’d like things to be different next time. Don’t assume that the person will change their behavior, or know that you have certain preferences.

Build trust and rapport.

When asked, “What do you think is the most important thing a remote manager can do to prepare their direct reports for success?” to almost 300 remote managers and employees, the #1 thing that they said was to “build trust and rapport across the team” (24% of remote managers and employees said this.) This should come as little surprise given how important social connection is in teams, to begin with, as discussed in Chapter 4. This means as a manager, making sure you’re prioritizing the different ways of connecting with your team beyond just the “work stuff.” Do you have regular video calls where your team can just chat about non-work related stuff? Do you have a dedicated chat channel where folks can have jokes shared, and small talk about their weekend? Make sure you’re investing in building connection in your team, as a way to set them up for success.

Make expectations for work results clear.

One of the best ways to set your team up for success if making sure they know the exact definition for “success” to begin with. Without clear expectations for what success is, your team isn’t going to know if they’re on track, off track… or anywhere in between. Make sure you’ve clarified these questions:

  • What does success look like? How will we know we will have been successful?
  • What does “good enough” look like?
  • What does “high quality” look like?
  • What are things I tend to be particular about that others might not?
  • How does this project tie into the bigger vision we’re trying to make real?

You can also read more about setting clear expectations for managing performance in Chapter 5.

Schedule regular one-on-ones.

You can’t make expectations clear, and you can’t invest in connecting with your team, if you don’t create the space and time to have these conversations. This is where one-on-one meetings come in. Of course, as a remote team, you’ll need to have these via video – but whatever you do, actually do them and don’t skip them. As described in Chapter 5, most remote managers tend to hold one-on-ones with greater frequency than managers who are co-located. This is valuable time to line up on what could be better, how the person is feeling adjusting to being remote, and what you can be doing as a leader to support them.

Help your team ease into being remote. Give them every reason to be successful by providing the support you know as a manager is your role to do. These six things will help.


  • Let people know that remote work is different – there is a learning curve.
  • Raise flags around overworking, loneliness, miscommunication, and a lack of deep work to help your team avoid these pitfalls.
  • Coach your team to lean into over-communication and empathy.
  • Build trust and rapport – 24% of remote managers and employees said it was the #1 thing you can do to prepare your direct reports for success.
  • Make expectations for work clear by asking questions like, “How will we both know we will have been successful?”
  • Schedule regular one-on-one meetings to help calibrate the transition to a remote environment.

Put this into practice with Know Your Team:

  • Use our Social Questions feature to build trust and rapport and help ease new employees into a remote environment.
  • Use our One-on-Ones tool to have consistent one-on-one meetings with your team, with agenda templates, suggested questions, and a place to write shared takeaways, so you can make sure your team members are adjusting well to a remote environment.