Virtual Retreats for Strategy Development & Strategic Problem Solving: 11 Design Tips and A Process

In response to the COVID-19 crisis, there has been a lot of discussion about alternatives to in-person conventions and trade shows. Yet, many executives and association strategists are also wondering whether viable virtual retreat options exist to replace in-person strategy development and strategic problem solving retreats.

The answer is: yes. One can host a successful, virtual, daylong strategy development or strategic problem solving retreat where those that are engaged at 9:00 am are still fully engaged at 5:15 pm. Ensuring a high level of engagement throughout the day and, most importantly, quality output at the retreat conclusion requires one to re-think the design of the overall strategy development process and the retreat design itself. 

In other words, it is unlikely that you can just take an in-person retreat design and move it online with success. Likewise, it is unlikely you can simply replicate the design of online business or Board meeting and achieve success. However, by applying the right design thinking principles and design elements one can achieve real success at a virtual strategy retreat, where participants are highly engaged throughout the day – and retreat objectives are realized. The fact is, just as successful online events require a different design than in-person events, virtual strategy retreats also require unique, virtual designs.

If you are in a bind and need to conduct a strategic problem solving or strategy development retreat right now to address the new reality or finish the strategy development process you’ve already started, most, if not all, of your focus will be on the virtual retreat design itself. However, if you haven’t started your strategy development process yet or have some breathing room you will want to design the entire process in a manner that takes into consideration the use of a virtual retreat.

This article focuses on the design of the virtual retreat itself and not the overall strategy development process. The concepts in this article apply to both strategy development retreats and strategic problem solving retreats.

Virtual Retreat Design Considerations

As is the case with most program design, one must take into consideration the needs of the stakeholders, retreat objectives, intended participants, available resources and the array of available methodologies. Of heightened concern for the virtual retreat designer is technology capability / limitation, delivering the same high quality outcome that an in-person retreat would deliver, and keeping all of the participants fully engaged and emotionally connected the entire day. 

Anyone who has participated in online meetings or webinars knows how challenging it can be to keep people fully engaged for even an hour, let alone an entire day – the key to a successful virtual retreat is to invest the time in and be intentional about retreat design. 

Virtual Retreats: Design Tips

  1. Change up methodology or activity approximately every 15 to 20 minutes. This is a critical practice to ensure daylong participant engagement.
  2. Use 15 to 30 minute long small group breakouts for a portion of every hour throughout the day.
  3. Provide breaks every 90 minutes. Make sure all participants know the break times, especially lunch, prior to the day of the retreat so they can make necessary food and beverage arrangements.
  4. Require that all participate via the online video platform. Resist providing an option for participants to call in via phone. Try not to create an unequal situation with part of the group convening in-person and some connecting via technology; there is a difference between ideal in-person and ideal virtual retreat designs.
  5. Provide clear participant instructions. Many participants may not have experience participating in daylong virtual retreats. Instructions should include information on tips for setting up the virtual workstation, staying comfortable throughout the day, optimizing the use of the technology, optional use of virtual backgrounds, materials participants will need, and food and beverage breaks. Ultimately, one wants to set clear participant expectations and make the participant experience as productive, easy and convenient as possible.
  6. Staff the retreat with a facilitator, host/tech person, and a behind the scenes scribe/assistant facilitator that can assist the facilitator with the real-time transcription and small group distribution of information captured during the retreat, for example large group brainstorming ideas.
  7. Part of a facilitators job is always to keep the audience engaged, in a virtual setting the import of this role is elevated even further. It is essential that the facilitator keep a heightened focus on keeping the virtual audience engaged and emotionally connected throughout the day.
  8. Open the retreat with a review of the technology tools that will be used.
  9. Capture brainstorming in real-time with live, onscreen handwriting. Connecting an electronic tablet into the meeting as a dedicated device to be used by the facilitator to capture ideas using a tablet pen and notepad app, in the same manner one would capture ideas on flip charts, may provide more flexibility than using an inherent system white board. Share the screen with participants when it is being used.
  10. Pre-determine who will be in each breakout group. In doing so, strive for optimal diversity and consider participant personalities and communication styles. Change the small groups assignments throughout the day so the same people are not always working together. Lean toward making the groups smaller than you might with in-person breakouts; five to six people per group works well.
  11. Consider identifying and training a member from each small group as a small group facilitator. The quality of small group output is often dependent of having a great facilitator. Facilitators should be chosen and identified before the day of the retreat. A good facilitator will keep the discussion on target with the end goal in mind, engage all group members in the dialogue and ensure that all contributions are considered. You may not need facilitators for each small group exercise; it will depend on the activity planned for the group. Prior to the day of the retreat provide small group facilitators with a list of their responsibilities and instructions.

Of course, a successful retreat relies on more than just that which happens during the retreat hours. Employing a sound process to design the retreat day itself exponentially increases the probability of success.

Virtual Retreats: Design Process

Define retreat scope: In a broad or macro sense, define the totality of the work you want to accomplish during the virtual retreat. In doing so, form the retreat’s overall boundaries related to topic(s) or general purpose. For example, is the scope of the retreat limited to solving one particular problem? Is it to develop an organizational strategy / strategic plan? Is it to develop a specific crisis management or issues management strategy? 

Define retreat objectives/deliverables: Precisely define what you want to “walk out the door with” at the end of the virtual retreat. In doing so, think about post-retreat next steps and exactly what you need and in what format you need it to successfully execute the next step. It is imperative that one clearly defines the precise retreat objectives/deliverables; it is not possible to design a virtual retreat without first precisely knowing what the objectives or deliverables are. If it is a strategic problem solving retreat, it is imperative that you precisely define the problem.

Identify the participants: As with any strategy or problem solving session, it is critical to have the right people in the room. So, take a strategic approach to identifying the participants. In addition to applying the Seven Steps to Optimal Diversity, make sure that all participants have the ability and are willing to fully participate online – meaning connecting via video and audio. If it is an in-person retreat in Miami and someone can’t make it, we invite someone else. Likewise, if someone can’t make your virtual “video” retreat, consider inviting someone else. Video enhances the quality of the communication by allowing for participants to better understand by being able to read facial expression and body language, resulting in better insight into the issue being discussed. Video also increases engagement. For those who are at home or in a hotel and don’t want to invite participants into their homes or hotel rooms, today, virtual backgrounds are available.

ID software platform: Make sure the platform that you choose has the features you need and is easy for participants to use. At a minimum, you will want a platform that has a chat function, allows multiple people to share screens and has breakout room capability. File sharing is another feature that you might want to consider. Also, confirm that your platform allows for daylong meetings; some free virtual conferencing software limits meeting length.

Identify methodologies: Identify an array of methodologies and activities that could potentially be used at different times throughout the retreat to achieve the retreat’s objectives. The more creative thinking, analytical thinking and prioritization tools one has to choose from, the better. Changing up methodology more frequently than typically done at in-person retreats helps keep engagement levels high throughout a virtual retreat. If the retreat is a strategic problem solving retreat, rather than a strategy development retreat, give consideration to various problem-solving methodologies and determine which methodology might be best to solve the problem at hand considering the virtual environment.

Design the retreat: Keeping in mind some of the tips listed above, design the day flow. Create a detailed facilitator schedule that effectively sequences all activities and modules, including breaks, and includes instructions and expected outcomes for each module.

Determine briefing materials. Based on the retreat design, prepare and distribute any necessary briefing materials, session handouts and worksheets.

Plan the post-retreat follow up: Further strengthen the social connection of the group through post-retreat follow up with the participants. Determine what type of follow-up will work best. Follow up could be as simple as an emailed thank you with a short summary of retreat accomplishments or as elaborate as seeking further input on a retreat item using polling software.

Click here to read about a global association of surgeons who converted their planed Strategic Action Plan Workshop into a daylong virtual retreat with participants from around the world as a result of COVID-19 travel restrictions.

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