Ten Best Practices for Delivering Fun and Productive Virtual Off-Sites

By Micah Zenko & Sabriyya Pate

The last twenty years have seen an explosion of innovations in virtual collaboration and video conferencing technology. Today, every corporate employee is armed with multiple ways to chat, collaborate, manage projects, and host video calls. Despite the ubiquity of these innovations, the face-to-face company off-site has persisted.

Why do tens of thousands of conferences happen every year – costing companies millions and dislodging employees from their routines? Because, usually, they are uniquely effective uses of time. The off-site persists because no amount or combination of technologies have replicated the energy, relationships, and clarity a good off-site can bring.

Meetings, and particularly offsites, provide leaders with an opportunity to sketch out their future vision, reinforce desired values and culture, and show their personality in a less formal setting. Off-sites also allow individuals to deepen professional ties, relate to their teammates outside of their ranks and roles, and take a more strategic view of the organization.

But with health and safety concern paramount, organizations will avoid unnecessary travel in the near future. So, how do you retain the best elements of an upcoming off-site while most of your company works remotely?

At McChrystal Group we have designed and facilitated thousands of in-person and virtual off-sites across industry and government. As you consider how to structure and run your own virtual off-site, here are a few of our best practices.

10 Best Practices for Leading Virtual Off-Sites

1. Encourage prep work

Prep work, including pre-readings, are especially effective in level-setting participants around an idea, concept, issue, or other topic. This shared learning, while done individually will allow participants at virtual off-sites to enter feeling prepared and confident to speak up. Also, when you are asking people to complete prep work, it is also important that you make it very clear why the prep work will inform the desired off-site objective.

2. Keep a central theme between all sessions

Successful virtual offsites require breaks at least every two hours. These breaks, which can be spread across days, can give the sense of comprising a series of meetings, rather than a holistic virtual offsite experience. To that end, it is extremely important that facilitators maintain a central theme for all the sessions. This theme should be re-emphasized in transition between sessions as well. Ideally, this brings more coherence to an off-site, and is more important in a virtual setting.

3. Break up the offsite with frequent activities

Humans have quite limited attention spans – common estimates cap them at roughly 6 minutes. Activities keep participants attentive and on their feet. Facilitators should not lecture, but rather guide participants to share the ideas, feelings, and thoughts that are tethered to the off-site objective. Activities keep participants talking and can often encourage discussion. Our various tools, from “parking lots” of ideas, to lighthearted ice breakers, to impromptu creativity contests, give our partners confidence in a memorable virtual offsite experience.

4. Don’t be afraid of silence when asking challenging questions

“Does anyone have a thought to share?” Long pause. Dead silence. We have all been there – and likely, we have been there more often since moving to remote work. Open-ended and challenging questions are often daunting to respond to. That is why it is important for facilitators to fear not and rather lean into the silence. “You won’t out-awkward me!” is a favorite space-filler of ours.

5. Require people to write down or type out responses before opening up to group conversations

Another best practice we have found to be effective when posing questions to a group is to require individuals to write down their responses, on a scrap piece of paper, an open note on their computer, or even in the video conference platform’s chat box. This gives individuals something to reference when called upon to speak and forces them to get specific and concrete when thinking about their responses.

6. Leverage technology to gather immediate anonymous feedback

At McChrystal Group, we are fans of tech tools like sli.do and digital whiteboards. Tools that allow facilitators to gather immediate and anonymous feedback are a critical differentiator for successful offsites, in our experience. Individuals most often disagree on a range of topics, but due to a range of cognitive biases, group think, hierarchy, and more, we are often incentivized to suppress our true opinions.

7. Ask questions that require quantifiable judgements or forecasts

Productive insights are rarely generated by the standard question: “what do people think?” Vague questions get vague responses. Instead, kick-start a group conversation with a question that requires a concrete, time-bound answer. For example, “what percentage of our company do you believe will be working full-time remotely in five years? The responses—ideally provided anonymously via chat—can reveal misalignments within your team about the trajectory of your organization. With that collective, quantifiable impression, you are ready to dig deeper into more meaningful “why” and “what should we do about it” questions.

8. Use breakout groups, smartly

We have found that the most effective breakout groups last 15 to 20 minutes. They should have 10 people maximum, in order to give everyone an equal and fair chance to speak. We have also found that trained facilitators, who are confident to assign roles, steer the conversation, and monitor group dynamics, are critical in such breakout groups. Without focus and a goal, these excellent tools for focused discussion can become distracted and ineffectual.

Another option is to allow participants to move through breakout groups. This functionality allows for the wider dissemination of information and allows off-site participants to choose the breakout group topic areas that most interest them.

9. Tastefully use slides and other reference materials

Video conferencing platforms now make it extremely easy to share slides and screens with participants. While helpful in simulating what would otherwise be a projector or screen at an in-person offsite, slide and screen sharing can detract the spotlight away from the faces of the individuals at the virtual off-site. For this reason, it is important to use slides and other reference materials strategically. Only show information that is relevant to what you are discussing in that moment. Do not be afraid to get creative with slide-builds, particularly when explaining a complex idea or framework. At the same time, remember that an attractive slide does not mean a useful slide.

10. Don’t assume what you do for in-person offsites will work remotely

There are so many examples of organizations that have been able to lead successful in-person off-sites. However, in a remote environment, not everything carries over. Most notably, the human connection enabled in in-person offsites, be it through high-fives and eye-contact, is lost in a virtual setting. This is why it is important to think intentionally about alternative substitutes. One simple example of this can be a technology platform that allows side-bar interactions, often the most valuable part of in-person offsites.

McChrystal Group’s overwhelmingly popular and successful offsites are now virtual.

At McChrystal Group, offsites are a part of our culture, and we have made the pivot to virtual offsites ourselves and are eager to share our methods with partners.

McChrystal Group’s Virtual Offsite, ranging in any duration from a few hours to 2-days, are facilitated on any partner-preferred video conferencing platform. Participants can expect to be engaged, active, and involved throughout the entire virtual off-site. Our offsites guarantee:

  • Strengthened trust and alignment around a common purpose
  • Increased team engagement by fostering a sense of belonging
  • Enhanced team performance by bolstering connectivity
  • Preserved strong company cultures

Our process for delivering virtual off-sites is simple. First, we collaborate with our partners to envision the desired end-state. Then, we design a tailored and engaging agenda that matches their end-state vision. Our team of world-class facilitators have led hundreds of off-sites and are prepared to alleviate administrative burden, while also bearing the brunt of keeping the session interactive, engaging, and productive.

Micah Zenko

Director of Research and Learning

Micah Zenko is the Director of Research and Learning at McChrystal Group, charged with the development and instruction of offerings designed to improve organizational performance through Red Teaming, strategic planning, and scenario development.

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Sabriyya Pate is an Analyst on the Solutions Team where she is responsible for researching and developing the firm’s products and solutions. She works with our decision-making portfolio and also facilitates Red Teaming.

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