How to lead effectively with a newly remote team

Phil Stern By: Phil Stern

The working dynamic for many companies changed overnight with thousands of businesses being suddenly forced to move to a remote workforce model. For many of these companies, their culture, norms, communication and collaboration have been built on the back of in-person interactions and real-time discussion. Many of these organizations will require a radical change in culture, processes and tools to drive their business forward.

We’ve identified three areas of focus to help your team manage through this change:

  1. How to help your team members work from home effectively
  2. How to drive culture and engagement in a newly remote team
  3. How to coach and lead effectively with a fully remote team

How to help your team members work from home effectively

  • Don’t take anything for granted. It can be easy to imagine the homes of your team members to be much like your own, but this simply might not be true. Ensure you check in with each member of your team:
    • Ask them if they have a quiet space to work
    • Ask if they need anything to help them establish a productive home office
    • Help them test their technology (internet, phone, etc.) to ensure it’s able to suit their needs. We suggest having each team member use a site like Speed Test. Their internet speed should exceed 5mbps for effective video calls (on a network they do not need to share with anyone). Recognize that if their kids are now home schooling they might need more.
  • Consider a stipend. To the point above, not everyone on your team is ready to quickly transition to remote work. To help make the transition smooth and to enable them with the best possible setup, consider offering a stipend to help cover their costs to acquire hardware, furniture or connectivity that will make them more comfortable and more productive.
  • Set clear expectations. Document your expectations for hours, activity levels, productivity and communication and share those with your team as early as possible. Review them in an all-team setting and then follow up with each team member in a 1:1.
    • Set a daily routine for yourself or stick to an established one. Share your routine with your team members and ask them to share theirs with you.
    • Establish guidelines for communication tools (how to use Zoom, when Slack is appropriate, etc.)
  • Engage with your teammates as much as possible. Effective collaboration can still take place from a distance and we recommend doubling your scheduled interactions with each team member, each week.
    • Standups, 1x1s, and other meetings should continue to be held on the same cadences via Zoom, with additional, shorter touchpoints also scheduled throughout the week.
    • Ensure all notetaking and presentations are in electronic form (Shared Word docs or Box) and share them after every meeting.
    • Be aware of lost “office interaction” and work to replace those by reaching out to say hello or offering support for an employee or co-worker.

Driving culture and engagement in a newly remote team

  • Start with empathy. Every interaction, be it with your team or an individual team member, is an opportunity for empathy and understanding.
    • Model this behavior. Start every meeting sharing how you’re feeling and ask others to do the same. Encourage your team members to share openly.
    • Understand that work and life is now blended more than ever before. Embrace and accommodate interruptions from children and pets. Laugh about them together.
  • Create new traditions. Given your team’s new realities about work and life, some of your old traditions and activities just won’t work anymore. Take this opportunity to establish new ones.
    • Lean into the work from home environment. Have people introduce their pets, kids or roommates. It’s a great chance to learn about your team members on a more personal level.
    • Try a virtual happy hour. Start a virtual book club. Try an online workout class or launch a Peloton or a steps challenge. Choose a charity to support as a group. Involve your team in the idea brainstorming. Have fun together while apart!
  • Increase your presence and visibility. This might sound counter-intuitive as you’ve just gone fully remote, but not being in-person with your team each day actually calls for greater presence and visibility on your part.
    • Hold Zoom office hours. Set up an always-on Zoom meeting and put the ID in your Slack profile or share it with your team via another format. Your team members can quickly pop in to ask questions or simply socialize.
    • Make a point to check in with each member of your team at least once a day via email, Slack, text or video call.

How to coach and lead effectively with a fully remote team

This sudden shift for many businesses and leaders also represents an opportunity to develop and deploy new leadership best practices. These are more important than ever now with a remote team.

  • Establish and communicate new guidelines for decision making. Given your new remote work paradigm, it can help to establish (or re-establish) how decisions get made.
    • Document and share with your teams who is involved, who is the final decision maker and what expectations are for timeframes and process.
    • We recommend establishing a model like RAPID or RACI to make ownership of projects and decision-making clear for your teams.
  • Share what you’re working on and ask your team to do the same. Because you can’t see each other in the office and will mostly be managing to measurable metrics, it can help to demystify what you and your team members are working on simply by sharing.
    • Each morning, via a 15-minute meeting, or via Slack or email, share out your priorities for the day or week. Ask your team members to do the same. Celebrate successes and review the previous day’s performance.
    • Take time each day to share wins (big and small) from members across your team. And share them with a broad audience. Celebrating achievements during this time is more important than ever.
  • Extend 1:1s and carve out specific time for coaching. So many coaching conversations happen in spontaneous moments on the floor. A team member pops by your desk or office to ask for guidance on a specific challenge they are facing. With your team newly remote, this may not happen with the same regularity.
    • Set an agenda for each 1:1 – even better ask your team members to set the agenda.
    • Carve out specific time for coaching in your 1:1s with team members.
    • Ask them to come to each meeting with their own topics for coaching and prepare one of your own. Use a framework like SBI to help them through specific scenarios or situations.
  • Expand your usage of existing collaboration tools and practices. Because there are so many changes happening at once for your team, documenting and sharing notes from each meeting, or helping them get quick access to necessary information will allow them to more easily adjust to new operating norms as they also internalize the myriad of other changes happening in their lives, their homes and in your business.
    • Take notes during every meeting and use shared documents that allow for collaboration in real-time (Google docs, Box, etc.) so that you don’t run into versioning issues or don’t lose docs that aren’t stored on shared drives.
    • You can also start using more advanced features in your existing tools. For example, Slack allows you to customize auto-responses in the tool for commonly asked questions. As your team adjusts to working remotely full-time, quick access to IT troubleshooting guides, step-by-step instructions for how to use your VPN and other commonly needed information can be automated within Slack.

Even under normal circumstances, it can be challenging to make the transition to having some of your workforce go to a remote setup. And under the current circumstances it’s nearly impossible to do so without making some missteps. Make this an iterative process and ensure you have a clear path for getting feedback from the team and adjusting your plan and policies accordingly. And finally, look for an opportunity to maintain some of these new practices and employee engagement tactics beyond this period disruption. They may serve you well in the long run.


Phil Stern
Phil is a Vice President at Mainsail. He leads the firm’s Center of Excellence for Sales and is responsible for helping Mainsail’s portfolio companies optimize their growth strategies and deploy sales practices.
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