A Practical Guide to Leading Thriving, High-Functioning Virtual Teams

12 min readJun 4, 2020

What does it take to successfully transition a team from the in-person office to virtual? Well, as countless companies globally are learning, the answer is: a lot.

Within Rippleworks’ portfolio of 100+ growth-stage social ventures, 97% don’t expect to be fully back in the office for the rest of 2020. Only 9% of Rippleworks ventures previously have significant experience working virtually. So, with this being the new reality for the time being, there is a lot we can learn.

Rippleworks convened ventures on an invite-only call to share practical guidance and actionable tips on how to lead thriving, high-functioning virtual teams, especially through COVID-19.

Ventures learned from two senior leaders with significant experience leading high-functioning virtual teams: Anne Raimondi and Sung Hae Kim.

Anne is a Rippleworks Expert and longtime advisor who serves as the Chief Customer Officer of Guru, a scrappy, fast-moving 250-person startup that is navigating the crisis in real time. She’s previously led high-performing teams as the SVP of Operations at Zendesk, Chief Revenue Officer at TaskRabbit, and VP of Marketing at Survey Monkey.

Sung Hae is Rippleworks’ Chief People Person, who most recently was the Chief People Officer at GitLab, the world’s largest fully remote company with 1,200 employees in 65+ countries. She’s led People Operations at small, medium, and large global organizations, including VMWare, HP, and Wizeline.

The practical guidance prepared by Anne and Sung Hae covered five critical topics for leaders of virtual teams:

  1. Preserving & Strengthening Culture
  2. Leading Virtually During Uncertain Times
  3. Equipping Managers
  4. Supporting Productivity & Engagement
  5. Working Asynchronously

Below you’ll find a writeup from the call that hopefully will be practically useful as social ventures navigate the COVID-19 crisis. In addition, we have shared the slides and compilation of ideas shared by our ventures.

1. Preserving & Strengthening Culture

Team culture is not a physical object, but transitioning a team to working virtually will quickly show how much teams rely on the physical objects to bring your team culture to life, such as the office environment and in-person interactions. Transitioning your company culture from in-person to virtual requires intentional design, planning, and dedicated work.

“Just like the pandemic is a UV light exposing cracks within healthcare systems, working virtually can shed a bright light on any cracks within your company culture,” Sung Hae said.

A helpful starting place is doing a quick assessment with a Culture Audit to identify priority areas you’d want to focus. Employee engagement surveys are also a quick way to gain inputs from across your organization.

In addition, you have to redesign deliberate ways for your culture to come to life in a remote environment.

What fun virtual ideas can you come up with to support your company values? Here are some examples we’ve seen for common company values:

Fun / Social

  • Slack’s Donut feature connects teammates for randomized social meetings (Zoona, South Africa)
  • Photo challenges where people shares on a theme: favorite mug, new hobbies, kid/baby photos (Sanergy, Kenya)
  • Weekly virtual cafeteria sessions for staff members to play online games together (Moringa School, Kenya)


  • Book clubs, lunch & learn sessions (Rippleworks, US)
  • Support employees’ ongoing learning through online platforms like Degreed (InVision, US)

Impact / Excellence

  • Small bonuses/gift cards to show appreciation for hard work (Cignifi, US/Brazil)
  • Short videos to share with the team that highlights innovations and progress, especially in the new normal (Sanergy, Kenya)
  • Allow everyone to contribute ideas for improving the company through online merge requests (GitLab, Global)

2. Leading Virtually During Uncertain Times

How you show up as a leader makes all the difference, and this is true more than ever in the virtual, COVID-19 world. We prepared practical ideas and tactics for leaders across three important themes: communicating directly, taking brave action, and maintaining optimism.

Communicating Directly

Communication is more challenging — but more critical — in a virtual environment, especially during uncertain times. How you show up as a leader and how you communicate creates the tone for your team virtually.

The first step for leaders is frequent listening to have a pulse on what’s happening with your team and your employees.

You can find multiple ways to ask questions to help your frequent listening beyond live conversations, including Ask-Me-Anything Q&As and Polls, using platforms like Slack, Polly, and Workplace. Slack has a poll feature that you can use to ask questions on a weekly basis.

Some suggestions for questions you should be inquiring about are:

  • What are you most excited about?
  • What are you most worried about?
  • What’s confusing?
  • What have I not asked that you’d like to share?
  • If you could change one thing, what would it be?

As you’re listening and understanding where your team is, constant sharing is especially critical when people are not physically together.

Here are steps you can take to adapt:

  • Adjust frequency — Consider having more (and shorter) all company meetings. Anne’s company (Guru) used to meet as a company once a month for 90 minutes. Now, they are meeting twice a month with a shorter format.
  • Add new formats — Leverage virtual mediums to communicate with the whole organization, such as long-form writing, message-based Q&As, recorded videos. At Guru, directly after town halls, company leaders host open office hours. “They have been really effective in mitigating the loss of casual conversations in the office,” Anne said.
  • Bring cross-functional teams together — Avoid the trap of teams sticking with themselves and creating virtual silos. Find and create opportunities to bring teams together to ensure cross-functional communication and collaboration continues.
  • Give context, then give it again — Context of decisions is paramount right now. Make sure it’s clear, and then keep repeating it.
  • Subtract what’s outdated —Focus and prioritization will help the team during virtual, uncertain times. Don’t be afraid to subtract things that aren’t working, and then clearly communicate it.
  • Ask for, and integrate, feedback — Make sure to understand how your communication is landing. Get real-time feedback and adjust.

Taking Brave Action

Making decisions can be harder in this time of uncertainty, because we don’t have all the answers.

It helps to use a decision-making framework, especially when you don’t have the answers but need to communicate to the larger team. We don’t know when, for example, we’ll be able to safely get back to our offices. You may not be able to share the answer, but you can help your team by sharing how you’ll make the decision.

There are a lot of different frameworks — First Round Review has 6 frameworks for startup leaders — so the most important step is for your leadership team to pick one that works for you.

The framework can be super simple — Guru uses a framework that breaks down potential decisions by Why we like it, Why we don’t, and How to mitigate risk.

Decision-making frameworks not only help make sure leaders don’t get stuck on tough decisions, they make it easier to communicate the decisions to the larger company.

A concrete example from Anne and Guru was a complex recent decision on compensation.

As we started to see that some of our customers were being impacted by COVID, we saw in our updated revenue projections that we would not be on track the way we had thought we were going to be.

We were right in the middle of compensation changes in March. The decision to make was: Do we go forward with these raises? Do we pause these raises? Do we push them off for six months?

As you can imagine, there were lots of strong, differing opinions across the leadership team, given the impact on our employees and how much we really do care about our employees and keeping them motivated and taken care of. This framework helped us make that decision less emotional, for each person to be able to list their pros, cons, and risk mitigation.

Ultimately, we chose to pause compensation adjustments. The risk mitigation we put in place was we had a small number of employees who were making below market, and so we were going to to allow ourselves some exceptions to bring people up to market.

I share that as a concrete example of how this framework helped us make a really tough decision, and how we used the framework to directly communicate with the whole company. So the takeaway here is if you don’t have a consistent decision making framework as a leadership team, to find one that works for you, and share that framework out with your team to give them context.

Maintaining Optimism

Optimism can feel like a big challenge these days. And what’s important to stress for leaders is that it’s not about faking positivity. Times are tough and uncertain.

But as you authentically process and feel negative experiences, your role as a leader is to identify and highlight positivity for your team.

In the book Scaling Up Excellence, Robert Sutton and Huggy Rao share how it takes five positive experiences to neutralize a negative experience.

Leaders can look for and communicate stories across your team and across your customer base where really amazing things are continuing to happen. These stories are vital and energizing as people are likely inundated with a lot of negative information and news.

At Guru, a practice that Anne and the leadership put in place is to highlight employees who are living the company values.

“One of Guru’s company values is ‘Give First.’ It’s been really amazing to see our employees volunteer, fundraise, donate in the time of crisis,” Anne said. “We’ve been able to highlight the good that is happening within our team, both at company meetings and on our Slack channels. It’s gone a long way in maintaining positivity and optimism, pointing out all the amazing things our team is doing.”

3. Equipping Managers

More than ever, managers within organizations have immense responsibilities on their shoulders. Not only are they the ones directly managing, coaching, supporting employees, they also are the ones likely with young children at home. Giving managers the tools and support to be success is vital to a thriving virtual team, especially in the current climate.

As managers directly manage teams and hold one-on-one meetings, they are a direct line of communication with your entire organization. Here are some ideas for better leveraging your managers:

  • Create a private communication channel for people managers. It’ll be a safe space to share resources & tips, ask questions, offer support. All leaders can then know what’s happening across the organization.
  • Host a bi-weekly meeting with just people managers to preview decisions, roll out company objectives, and absorb decisions before company-wide announcements. Managers ultimately will be the ones directly delivering and supporting company-wide decisions.

Another way to support your managers is to help them rethink how they hold one-on-one meetings with direct reports. With the new virtual environment, clarity and alignment are more important than ever. Help managers know what questions they should be asking their direct reports, such as:

  • “What do you want to spend time on when we meet?”
  • “Are our company and team goals and outcomes clear, aligned, and prioritized? If not, where can we improve?”
  • “What can I do to help you the most?”

Finally, support managers by helping rethink how to manage performance and give feedback virtually. As a company, you will want to revisit how to conduct company-wide performance management (consider creating a lighter, less frequent version for the virtual environment).

Key tips for managers for virtual performance reviews are:

  • Leverage writing: Share a written summary of topics ahead of time
  • Ensure psychological safety: Make sure to lead with what the employee is doing well
  • Focus on what’s realistic: Narrow to at most two areas for development over the next period of time, especially for what is realistic given the current situation

4. Productivity & Engagement

When it comes to team productivity, it’s important for company leaders to take a step back and remember that your team is not just working from home — they are working from home during a global pandemic.

As leaders work to support productivity and engagement from their teams, they need to reset expectations and what success looks like. To ensure teams remain focused and motivated, leaders should:

  • Prioritize & focus: Be very clear about what the 2–3 most important business outcomes are during the next period of time. Resist taking on shiny new objects.
  • Continually inspire: Turn up volume on sharing stories about customer impact and purpose — how are you inspiring your teams around your shared mission more than ever?
  • Provide direct support: There is a lot happening in people’s lives right now. Embrace flexibility and look out for one another. Create programs to help with other challenges in their lives that exist outside of their work.

And as you ask your team to continue contributing their best work, it’s critical to continue providing an engaging team working environment.

M-KOPA (Kenya/Africa) has seen team engagement improve by 15% since pre-Covid. Their activities include company yoga classes and weekly coffee breaks (informal 30 mins video chats) between 5 randomly selected staff and senior management.

We’ve compiled more creative ideas we’ve been seeing across our portfolio here. Some highlights are:

  • Different team members hosting “story time” for each others’ kids
  • Leadership team sharing personal videos with context and encouragement
  • Virtual dress up days
  • Scavenger hunts on Zoom / video conference
  • Employees volunteering to host sessions sharing pandemic hobbies
  • Surprise the team with a day off for the whole company

5. Working Asynchronously

An upside of working virtually is that when it’s done well, productivity can increase. A downside is that when it’s not done well, productivity can decrease with more fatigue and burnout. How do you make sure you are getting the upside and avoiding the downside? Setting up your teams to work asynchronously is a huge part of the success.

  • Prioritize results and outputs. Be clear on due dates. Don’t make the work be about face time or hours.
  • Encourage asynchronous communication. Digital messaging (Slack, chats, emails, working docs) allow you to communicate without having to meet on a call. Align on clear guidelines on how the team will use asynchronous communication.
  • Create transparency & documentation. The more your team can access the information they need without having a direct conversation live with others will enable teams to get work done quickly on their own time. Ensure you have a “Single Source of Truth” for dynamic information.
  • Book “flow” time. We all feel the “Zoom Fatigue” after a long day of back-to-back virtual meetings. Virtual calls be draining, and they often hold us back from getting our work done. In addition to rethinking your team’s approach to meetings, make sure people are blocking “flow time” on calendars reserved for avoiding meetings and getting work done. Teammates need to honor it by not scheduling meetings during those times. Leaders can/need to model this for the larger team.

Speaking of too many meetings, limiting the hours spent in meetings is a critical step for asynchronous virtual teams. As meetings take place, encourage your teams to:

  • Have shorter meetings. At Rippleworks, we’ve been experimenting with shorter meetings. Did you know Google Calendar allows you to set default meetings to either 25 minutes or 50 minutes (instead of 30 or 60 minutes)?
  • Set clear agendas. Before booking a meeting, make sure there is clarity on what needs to be covered and expected outcomes. Double check to make sure you need to hold the meeting (and it can’t be an email), and prepare and send as much information as you can in advance.
  • Be strict on attendees. Invite only ‘must-have’ people to meetings. Record team meetings for people to view on their own time.

Silver Linings of COVID-19 Virtual Work

Successfully transitioning to become thriving, high-functioning virtual teams not only ensures ventures advance their work during uncertain times, the lasting benefits can continue much longer — whether ventures stay virtual or not.

COVID-19 has brought the mandate to rethink and grow how your company works together, whether it’s better living team culture, growing the ways to lead and communicate, or building more flexibility for teams to be productive.

“The real opportunity and silver lining for me is to see the humanity of it all. Something changes when you see inside people’s homes and there’s toddlers on people’s laps and there’s dogs and cats in our Zoom meetings,” Anne said.

“This is an opportunity for us to think about how we can work better and also how we can help people live better,” Sung Hae said.