How to Transition Your Team to Remote Work

10 tips from the world's top remote experts on how to navigate the transition to working remotely.

Transition Your Team to Remote Work

Planning a transition to remote work isn’t easy – but having the right tools and practices in place can make a big difference.

In light of the world’s current situation, we asked a panel of remote work experts for their tips on how to effectively transition a team to working remotely.

Whether you’re managing a remote team for the first time or telecommuting is something that you’re already familiar with – these tips will help you foster communication, set clear expectations, and support your team during this transition.

1 Establish documentation practices

If your team doesn’t have an internal wiki or digital employee handbook, now is a great time to create one. As Sid Sijbrandij, CEO of Gitlab, tweeted during our #ManagerChats:

According to the Gitlab team handbook, documenting decisions in one central location saves time in the long run and helps the company scale and adapt quickly.

Job van Der Voort, CEO of Remote, shared a similar piece of advice:

Finally, Joshua Schnell, Director of Marketing at BuySellAds, emphasized the impact that great documentation practices can have when onboarding remote employees:

2 Create a remote work policy

In order to have a smooth transition to remote work, it’s important to create a set of guidelines or “rules” that employees should follow when working from home (or locations other than the office).

As Erin Blaskie, Director of Marketing at Fellow.app argues, leaders transitioning to remote work for the first time need to create a remote work policy that is easy to follow and understand:

Similarly, Cris Mendes said that gathering specific tips and guidelines for each department has helped the Drift team transition to remote work successfully:

👉 We compiled a list of 10 remote-first companies and some of the remote work policies that have helped them be successful here.

3 Schedule recurring check-ins and team meetings

One of the most common mistakes to avoid when leading a remote team is not checking-in with your direct reports on a regular basis. If your team is transitioning to remote work, it’s important to schedule recurring one-on-one meetings where you ask employees if there’s anything you can do to support them.

As Sam Mallikarjunan, CRO at Flock argues:

Just like regular one-on-ones can bring structure to your direct report’s schedule, regular team meetings can help you ensure that the team is aligned and motivated. Here’s what Aydin Mirzaee, CEO of Fellow.app, said about the importance of scheduling these meetings – and increasing their cadence if necessary:

4 Trust employees to do their work

A lot of leaders transitioning to remote work for the first time worry that their employees won’t be as productive as they were at the office. However, this is a common assumption that you should avoid. As Heather Doshay, VP of People at Webflow argues, leaders should eliminate micromanagement in this type of situations:

If somebody on your team is not producing the work they’re expected to, don’t assume that they haven’t been working. Instead, check-in with them and ask if they’re struggling with something and if the expectations were clearly set.

Finally, it’s important to remember to focus on your team’s output – and not the number of hours that they are working. As Matt Mullenweg, CEO of Automattic said during our Twitter chat:

5 Set clear goals and expectations

Don’t make assumptions about things that may seem obvious to you. Instead, write down clear goals for every new process, project, and team ritual:

Now that your team is working remotely, team members are probably communicating less often than they’re used to – that’s why it’s important to communicate and reiterate your team goals and important metrics.

As Joe Martin, VP of Marketing and Strategy at Cloudapp argues, setting clear expectations and OKRs is key to a smooth and successful transition to remote work:

6 Provide employees with the right remote tools and office equipment

One of the most important things you can do as a remote leader is empowering your team with the right remote tools. As Tayo Rockson, CEO of UYD Management argues:

👉 Here’s a list of 9 tools you can use with your remote team

On the other hand, it’s important to check-in with your direct reports and ensure that they have the office equipment they need to be productive at home. As Sarah Park, president at MeetEdgar said during our chat, this could be a game-changer for your remote team:

7 Translate your company’s in-person rituals to virtual ones

Transitioning to remote work doesn’t mean that your company rituals (for instance, all-hands meetings) should stop.

As Leah Knobler, Director of Talent Acquisition at HelpScout said, when it comes to working remotely, it’s important to get creative and have some fun:

8 Provide flexibility and mental health support

This is not a normal circumstance to be going remote in, so the most important thing you can do right now is being empathetic and providing your team with as much flexibility as possible. That’s one piece of advice that Phil Gamache, Marketing Operations Manager at Close, shared during our chat:

9 Establish work-from-home boundaries

Apart from providing employees with flexibility and emotional support, it’s essential to remind your team to maintain a balance between “work-life” and “home-life” when they’re working from home. And of course, as a leader, you should set the example.

Here’s what Michael Lopp (Rands) and Jean-Michel Lemieux, CTO at Shopify, said about this:

10 Encourage social time and team bonding

Last but not least, remember to create opportunities for casual conversations. As Jonathan Ronzio, CMO at Trainual argues, you shouldn’t only talk about work during your virtual meetings and video calls:

Here are a few tactics to encourage your team to have those “watercooler conversations”:

Follow these 10 tips for a smooth transition to working remotely

  1. Establish documentation practices.
  2. Create a remote work policy.
  3. Schedule recurring check-ins and team meetings.
  4. Trust employees to do their work.
  5. Set clear goals and expectations.
  6. Provide employees with the right remote tools and office equipment.
  7. Translate your company’s in-person rituals to virtual ones.
  8. Provide flexibility and mental health support.
  9. Establish work-from-home boundaries.
  10. Encourage social time and team bonding.

Finally, don’t forget to check out Fellow.app for your remote meeting agendas.

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