A One-on-One Template For Switching Your Team to Remote Work

Around the world, offices are silent and empty, and employees are working from home in an attempt to combat the coronavirus. Though the shift to remote work predates the crisis, it has profound implications on how managers lead their teams that will continue long after self-isolation is over.

If you’re exploring remote work for the first time, it doesn’t have to mean you’re cut off from your team. It does, however, mean you have to be much more deliberate in maintaining your relationships and finding opportunities for meaningful communication.

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In practice, that means putting a lot more emphasis on your one-on-one meetings. They’re your best chance to have some face-to-face contact, keeping up to date with your team’s progress, and offer your support. Here, we’re giving managers a template to use in your one-on-one meetings after switching to remote work. Use it to learn what each individual needs to be successful while working remotely and to reassure them that while the physical circumstances of work may have changed, your care and commitment remain the same.

A One-on-One Template for Introducing Remote Work

Introducing remote work–whether it’s because of the current crisis or simply a part of the larger trend toward teleworking–requires a great deal of care to ensure the transition goes smoothly. 

With this template, you can help ease that transition by making sure each member of your team has the physical and emotional resources they need to thrive under these new circumstances. You can also gather vital information about your team’s well-being and practice the new communication skills you’ll need to keep your relationships strong.

How to Use This Template

Below are questions you can ask of your employees to help them navigate remote work. Feel free to ask the questions as they are, or add them to additional questions you’ve ideated that are relevant to your specific circumstances.

Regardless, make sure to ask your team members in-depth questions about their environment and state of mind. This isn’t a checklist you can race through; it’s a chance to really connect. Understand that members of your team may have concerns that they are initially reluctant to tell you about, so draw those out by asking follow-up questions.

We highly recommend using a video app such as Zoom for your one-on-one meetings, so you don’t lose out on the ability to make eye contact, read body language, etc.

Finally, be sure to take notes about each team member’s response, so you’ll know which issues to come back to in your next meeting. (Uptick helps organize those notes, so it’s easy to refer to them in the future!)

Why Use This Template

Working from home will require new skills for both you and your team members, and this template can help you get in front of some of the common challenges remote teams experience. 

In a 2019 survey of remote workers, 27% reported that their #1 challenge was communication, followed by social opportunities and feelings of loneliness and isolation. Setting appropriate boundaries around work is another common issue. Some workers struggle with procrastination and distraction, but many also report working longer hours than they would if they were at the office. It’s important to gauge how your team members are coping with these challenges, and let them know that one-on-ones are the place they can share those issues with you.

Remote work also presents some particular challenges to managers. (We know because we’ve been there.) If your usual MO is to take the pulse of your team by reading their body language, chatting with them over lunch, or physically looking over their work, losing those interactions can make you feel like you’re flying blind. This template will let you check in much more meaningfully than you can over email or Slack, so neither you nor your team members feel adrift.

When to Use This Template

We recommend asking these questions in the first week or two after starting remote work. Give team members a little time to find their footing, but don’t wait so long that they develop bad habits or feel adrift.

Just as importantly, the questions on this template aren’t meant to be asked once and then forgotten about. If team members voice concerns about any of these issues, come up with a strategy to address them, and then follow up to make sure it’s working. 

Remote Work One-on-One Template

  • What parts of working remotely do you think might be challenging?
    • Isolation? Difficulty asking colleagues questions? Lack of access to management? Not knowing how to use remote tools?
  • How can I help you with these challenges?
    • Do you want me to check in on your time management regularly? Do you need a quick lesson or refresher on how to use any of our tools?
  • What parts of working remotely are you excited about?
    • Schedule flexibility? Deep focus time? Having your pets as officemates?
  • What is your remote work routine?
    • What time do you start work? Do you take breaks? When do you stop for the day? Do you find it difficult to get started in the morning? Do you have a hard time letting yourself stop in the evening?
  • What is your physical setup for remote work?
    • Do you have a second monitor? Are you working from a desk, the kitchen table, or (hopefully not) from bed? Are you working from a private office or a shared space? (If possible, offer to provide tools that would make their space more conducive to work.)
  • How are you handling distractions?
    • Are your family members/roommates also at home? Are you finding the internet more distracting than usual? (If so, suggest productivity tools to better manage time.)
  • Do you find you’re more or less productive working from home?
    • Have you seen any change in the quality of your work? Your ability to make deadlines?
  • How would you rate the quality and frequency of communication with the team since you went remote?
    • Are you able to get timely answers to questions? Do you find internal messaging helpful or distracting? Would you like more or less communication with me throughout the day?
  • Are you feeling socially isolated, or do you have social outlets?
    • Do you have friends, family, or roommates to interact with? Are you getting out of the house to exercise or pursue hobbies? (If not, brainstorm some team-wide activities team members can do even while working separately.)
  • Do you feel our current tools for remote work are adequate to meet your needs?
    • How would you rate our videoconferencing tools, internal messaging tools, etc.? Is our internal documentation accurate and accessible when you have a question?
  • Do you feel you understand the expectations about remote work or any of our policies?
    • Are you clear on the hours and schedule you’re expected to keep, your availability on Slack, etc.? Do you feel comfortable using sick days or asking for flexibility to fulfill your social/familial obligations?
  • What could we be doing to make this situation easier for you and the rest of the team?
    • More/fewer team-wide meetings? More/fewer Slack conversations? Greater flexibility about scheduling?

Embrace Remote Work, Resist Isolation

While the coronavirus pandemic will eventually pass, the questions on this template will only increase in relevance as more and more workplaces allow for some level of remote work.

Even if you feel totally comfortable with this way of working, it’s still important to return to these questions from time to time. The stress of COVID-19 will undoubtedly wear on your team members as the weeks go by, and new issues will surface. The same is true if team members experience a significant change in environment, like a move. Stay attuned to these changes, and use these questions as an opportunity to show you care.

A big part of managing a newly remote team is maintaining strong connections, so when everyone sits down at their laptops, they still feel like they work as part of a larger whole, instead of as scattered individuals. One-on-ones are the best tool at your disposal for keeping those relationships strong, maintaining accountability, and improving your team’s processes. Those are goals that will always be moving targets, even when going to work means not moving at all.

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