Start-to-Finish Guide to Planning Virtual Team Retreats

There are a variety of reasons why teams are holding virtual team retreats on a more regular basis, including:

  • The team is unable to meet because of travel restrictions.
  • The team is made up of talented remote members who are geographically dispersed.
  • The organization is looking to reduce travel expenditures and allocate those resources to facilitation support from an organization effectiveness or learning and development vendor.
  • The team is struggling and needs to meet as quickly as possible.

Virtual retreats are a useful alternative to in-person retreats—not just during difficult times like when a global pandemic occurs. Retreats can help colleagues get to know each other better, overcome challenges, make decisions, engage in skill-building, or collaborate on plans and strategies.

If your team or a team in your organization needs to plan a powerful virtual retreat, use the following steps as a guide to plan and execute a memorable and results focused experience for everyone.

1. Determine the Purpose and Goals

Generally, people have high expectations of a retreat and hope that it will be an effective use of their time. Before getting too far into the planning process, you (and your team, if appropriate) need to clarify the key goals and outcomes you want to achieve. What is the purpose of your retreat? Do you need to give the team a chance to reconnect and recharge? Do you need to share new information about an important change or initiative? Does your team need to evaluate a problem or discuss a decision? Does the team need to collaborate on a strategic plan?

The purpose and goals will shape the overall theme and direction for the retreat, so it is important to be explicit and keep the purpose very focused. Keep in mind that in a virtual setting, you are more limited in what you can accomplish, and a clear purpose will inform other decisions and actions in the planning and preparation process.

2. Identify Topics and an Agenda

With the purpose and goals in mind, you can identify specific topics to address and shape those topics into an agenda. If you are unsure what topics to cover or want input from others, consider a short survey or planning discussion. Being collaborative in the planning process can build team member interest in the retreat. Again, be cautious that you don’t take on too much and overwhelm people with multiple topics that cannot be sufficiently covered in the time available.

3. Build the Structure

With the purpose, goals, topics, and agenda in mind, you are ready to make decisions about how to structure and execute the retreat itself. Here are some key questions to consider:

  • How long will the retreat need to be to accomplish the goals and cover the topics sufficiently?
  • Who will attend?
  • Who will be the retreat leader? Is a vendor partner needed to provide facilitation services or lead exercises and activities?
  • What is the budget?
  • What materials or resources are needed?

As you structure the virtual retreat, look for ways to vary the delivery method, so you can keep engagement and productivity high. Consider approaches such as:

  • Full group work.
  • Small group work and breakout sessions.
  • Pre-work and preparation materials or assignments.
  • Collaboration technology like virtual whiteboards, sticky notes, polls, and surveys.
  • Exercises, activities, or simulations.
  • Supporting content, data, or resources for team members (printed or digital).

4. Manage Logistics

With most Virtual Team Retreats the most crucial logistical concerns are related to technology. Have team members test their connections and software well in advance of the retreat. If you are the retreat leader or working with a facilitator, rehearse key elements of the agenda and the technology.

People like information at their fingertips, so when you provide details about the meeting, include information like the date and time, objectives, instructions about how to join the meeting, and if camera use is needed or expected. Oftentimes the technology platform you use has options to support scheduling and details. For geographically dispersed teams, don’t forget to consider time zones and how that will impact various team members. It might be appropriate to provide a few reminders to participants in advance.

Prepare and provide supporting materials ahead of time so you don’t have to wait for people to access documents and resources during the retreat. If you are planning to do a screen share, be aware of file locations so you can execute the screen share efficiently.

5. Execute and Follow Up

When the time comes to execute the retreat, be flexible and willing to adapt as needed. There are dynamics in a virtual team retreat, like technology interruptions, that do not occur in an in-person retreat so avoid getting frustrated when this occurs. Do your best to troubleshoot and make it the best experience possible.

Throughout the retreat, keep notes or a summary of assignments, action items, due dates, and next steps. If you are actively involved in the facilitation of the retreat, you might ask someone to help you with this responsibility so you can remain focused on leading the meeting. Then, distribute a summary of key points and action items to be completed after the retreat. When following up with an action plan, include details such as due dates and who is responsible in order to create greater alignment and transparency.

One of the often-overlooked parts of a virtual retreat is the follow up that should occur. Invite and be open to feedback about what worked well and what could have been done more effectively. Check in with participants who may not have been engaged because they may reveal information about how you can more constructively engage people in future retreats or indicate issues that need to be addressed related to the topic or plan of action. Connecting with team members will create open lines of communication that will benefit the team in many ways.

With some thoughtful preparation, you can achieve higher levels of engagement, collaborate on solutions, and make your virtual retreats a positive experience for everyone, even when working through challenging issues or problems with others. Check out CMOE’s free digital course, Leading Virtual Meetings for some helpful tips and ideas on leading virtual team meetings of all types, including retreats. If you are looking for a partner to help plan and facilitate a team retreat, contact CMOE to learn more about our extensive experience leading virtual and in-person team retreats.

Is a Virtual Retreat Right for Your Team?

If you are still exploring whether a virtual team retreat is right for you and your team, here are answers to some common questions that will help you make the right decision.

How are virtual retreats different from in-person retreats?

Virtual retreats can have cost benefits over in-person retreats but usually require logistical coordination similar to an in-person retreat because you have to get more creative about how to accomplish objectives and use technology to build a highly engaging experience. Some people falsely assume that a virtual retreat requires less time to organize. In actuality, the planning of a virtual retreat can take just as long as planning for an in-person retreat.

Savings can be found with virtual team retreats by eliminating airline and hotel fees but are often re-allocated to facilitator support, technology tools, and even motivation gifts.

What are the upsides of virtual retreats?

Here are some of the primary benefits of a virtual team retreat.

  • Critical or time-sensitive decisions can be made from remote locations.
  • Advancements in technology and collaboration tools make virtual team retreats more effective and collaborative than ever.
  • Most people have become more comfortable with virtual meeting technology.

What are the downsides of virtual retreats?

Here are some of the drawbacks of a virtual team retreat.

  • People miss the benefits of human interaction and seeing subtle reactions and body language.
  • Team members may not get the same opportunities to strike up spontaneous conversations that reveal important issues or build strong relationships.
  • There can be some frustrations and interruptions with technology.

How do you make a virtual retreat fun?

The best way to provide the ultimate team retreat is to incorporate team-building activities or exercises that foster participation and engagement. These can be simple activities ranging from ice-breakers to extensive activities or simulations that have a strategic connection to the retreat goals and objectives. Don’t hesitate to tap into the creative minds of your team members. They will likely have ideas about what will make the retreat fun and effective.

Some practical ways to promote engagement and have fun in a virtual setting include:

  • Begin or end the retreat with a virtual happy hour or coffee shop.
  • Use a virtual team-building activity or simulation.
  • Ask each participant to select a virtual background that represents something unique about them.
  • Start with a reflection question or quiz that participants can discuss.
  • Play a trivia game.

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About the Author


CMOE’s Design Team is comprised of individuals with diverse and complementary strengths, talents, education, and experience who have come together to bring a unique service to CMOE’s clients. Our team has a rich depth of knowledge, holding advanced degrees in areas such as business management, psychology, communication, human resource management, organizational development, and sociology.