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How to hold a strategic planning session virtually

Stephanie Kusibab
April 15, 2020
How to hold a strategic planning session virtually

Replacing that one- or two-day in-person strategy session with a virtual process may seem far-fetched. But it is possible. And, not just possible, but practical. 

With modern technology and a good facilitation plan, you can still bring people together to think strategically and co-create for the future. In fact, in this uncertain environment, strategy is more important than ever, and exploring different scenarios is increasingly critical to respond to and get ahead of change. 

Strategic thinking is best done in groups, not by one or two people. But right now, as the world grapples with the coronavirus pandemic, bringing people together physically has suddenly become ill-advised, if not impossible. Thankfully, these types of conversations can still take place just as effectively as before. Like so many things right now, it just takes a different approach.

With a strong virtual platform that allows for video interaction, breakout groups, and nonverbal feedback, we can simulate the in-person experience. No, it is not quite the same. But it can be effective with a little planning and ingenuity.

Braving the Unknown

Two years ago, I had the opportunity to do just that for the first time. We were establishing a new association – globally. With task force members in Europe, Asia, South America and North America, plus sponsor personnel who were traveling the globe, we did not have the budget to bring them together physically to have the required founding conversations. We HAD to do the planning and decision-making virtually – with a group of people who had never met in person, were not native English speakers, and who had different cultures and business backgrounds. 

It was uncharted territory, but we created a plan to do the work over a 12-week period. We opted for a scrum approach, taking on the vital tasks in succession in short, two-hour sprints via video conference. It took some patience and ingenuity, but it was also totally enjoyable. The team came together, accomplished something amazing, and I count the task force members as lifelong friends and colleagues.

4 Essentials of an Effective Virtual Strategy Session

Here are some of the lessons we learned from that work, and projects since, that you might find helpful in planning your next virtual strategy session or project:

Lesson #1: Build your team

As with any group endeavor, it is important to get to know the people you are working with. We were intentional about building a sense of team from the beginning.

We set out clear goals and took the time to get to know each other on the first call – nearly an hour just on introductions. This set the groundwork for trust and respect, allowing us to quickly get to the heart of the matter about the difficult decisions we were making. With a sense of collaboration and mutual respect, we moved effectively through meaningful, thought-provoking dialogue to decision-making.

If your group already knows each other, don’t skip the team-building step. Spend some time catching up, introducing new members and strengthening connections. Then, be sure to set clear team goals to guide your activities and bring everyone back on track when the discussion starts to wander.

Lesson #2: Prioritize discussion

Just like an in-person meeting, your time together is limited and precious. Make the most of it. We sent out pre-reading in advance to provide background, share important information and set the tone for the upcoming meeting. This kept the PowerPoint slides and presentations to a minimum and allowed us to use the majority of our calls for discussion and decision-making rather than conveying information.

We used breakout sessions during the calls to ensure everyone had the opportunity to contribute. Breakouts also helped to build consensus and speed decision-making. We set time limits for each discussion to keep things moving forward and ensure the groups stayed on task.

Even with a strong plan and dedicated facilitator, the team chose to add two unplanned meetings during this timeframe to further discuss specific topics. (Plus, we all really enjoyed the work and each other’s company!)

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Lesson #3: Expect the unexpected

Someone will have a bad internet connection. Calls will drop. Topics you thought would elicit little discussion could end up taking hours. These things happen. Remaining flexible and adjusting the plan is all part of the process.

For example, we thought developing the mission statement would take multiple distinct discussions across two meetings. With one breakout session and a full group discussion, it was done. We thought setting strategic goals would be quick given that this was a start-up with clear operational needs.

Turns out it took two and a half meetings to prioritize and hash out where the fledgling organization would focus its initial efforts. But listening to participants, understanding the group dynamic, and staying flexible is critical in any group workshop.

A virtual setting is no different; you just might need to pay a little closer attention so technology doesn’t become a distraction.

Lesson #4: Don’t be afraid of technology

In any group, there are some people who are more comfortable with technology than others. Lean into that. Plan for it. Allow extra time to help those who need it before the first call. Do quick tutorials to introduce features of the platform you’re using as you go. Let everyone help each other. Assign those who are more tech savvy as note- takers who can capture the small group discussions live on-screen and share them visually during the large group discussions.

We made a point of asking everyone to use the technology platform from the beginning by having them share pictures/slides of themselves as part of their introductions. This allowed each person to get comfortable sharing their screen and navigating the technology from the first call. When it was time for our first set of breakout groups, we learned from the teammate calling in from his hotel room in Singapore that our platform drops those who had called in via phone rather than computer. Good to know. We troubleshot that one in real-time and got him back on the call ASAP. But, that didn’t deter anyone. We knew we were all in it together and embraced exploring and teaching each other as we went. 

As we are all well aware at this point in history, sometimes you just need to embrace the unknowns of a new technology platform in order to get to the good stuff of collaboration and breakthrough ideas. Remember, technology is the means, not the end.

By understanding your goals from the beginning, and focusing on teamwork and exploring together, strategic dialogue is still possible despite physical distancing.

The Wrap-Up

Build a strong team. Use time wisely. Be open and resilient. Learn from each other. With this simple formula, you can continue to host effective strategic conversations virtually and ensure your organization is prepared for a successful future.

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Stephanie Kusibab

Stephanie Kusibab is an accomplished and versatile strategy consultant with more than twenty years’ experience delivering programs that accelerate growth and drive mission impact. Through broad business experience and perspective, she quickly understands and assesses a situation to identify growth opportunities across industries and professions. Stephanie believes the most powerful ideas come from bringing people together. Through deliberate, structured interactions digitally and in-person, she helps organizations tackle high-stakes conversations, mine diverse perspectives, generate new ideas, build stronger teams, and understand market opportunities. Stephanie and her team at Essentiam assist client organizations in defining their future through strategic planning, mission and vision creation, market analysis, leadership development, identification of new business opportunities, new product development initiatives and strategy coaching.

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