How to Lead a Remote Strategic Planning Session

Right about now, many ImageThink clients are realizing they need to host a remote strategic planning session. The forced move to working from home isn’t working for everyone, and 2020 has thrown a lot of teams and companies for a loop when it comes to cooperative and collaborative meetings. (Read our tips for elevating virtual meetings and leading creative virtual brainstorms for some helpful thoughts.)

Virtual Strategic Planning Sessions benfit from a shared agenda.

The global pandemic, slowing economy, and necessity of social distancing has set many companies behind and made goals set last year seem utterly unattainable. But don’t let the challenge of working from home scuttle 2021 with an unsuccessful strategic planning session.

As we move into what we like to call strategy season, ImageThink is helping clients capture and leverage their most valuable insights from a tough year, even in a virtual environment. We’ve collected some of our favorite pointers for doing so below.

What You See Is What You Get

Meeting together in person is a whole body experience. You mingle by the coffee, smell the whiteboard cleaner, notice your attention drifting to the window every so often. But most importantly, you instinctively pick up on far more conversational cues than are readily perceived online. Things like body language, eye contact, the understood excitement when multiple people try to jump in on an idea.

The wall of faces we often encounter on a remote meeting can often contribute to Zoom fatigue.

Instead, most online conference applications require participants to look at a Brady-Bunch inspired tableau of talking heads (including their own), or worse, a wall of black tiles with their colleague’s initials. Occasionally someone will share their screen, and the company’s best and brightest get to watch the words slowly populate, character by character in a Word document.

It’s not exactly inspiring stuff, and it instantly kills any momentum generated around a good idea. It’s also not as fast as operating together in real time around a whiteboard or flipchart, and many of the online versions of those tools haven’t quite cracked the experience.

Including a graphic facilitator, who can help guide and record your remote strategic planning session visually, share their screen as they write, draw, and map out your best ideas dramatically increases attendee attentiveness, participation, and feelings of value as they see ideas marked and added to the board. Not only is the content more engaging in the moment, but it is more memorable, and provides a clear map of next steps and action items, with owners that your team can refer to moving forward.

Not Everything Has to be Done Live!

When we work with our clients remotely, we also build in additional time to prepare templates and visual frameworks that we’ve found increase creativity and help participants remember key takeaways better.

A pre-fabricated template for visual journey-mapping

Part of the challenge of remote meetings, is that they fail to capture the fluidity and conversational nature of their in-person counterparts. Businesses are competing with technology, disparate time zones, and also every individual employees work-from-home setup.

It’s why as we work with more and more clients who have gone to full remote setups, we have baked in more planning time, and encouraged the use of templates, frameworks, and pre-made visual elements to help jump start the brainstorm, meeting, or remote strategic planning session. We find these elements help to open people up, who are missing the traditional pre-meeting preamble and chit chat.

Remote Strategic Planning Takes Longer Over High-Speed Internet

On that note about planning, perhaps the greatest tip we can offer is to allow more time. Space your sessions out. It’s natural to suppose that in the absence of travel, bathroom breaks, breakfasts and lunches, that these important meetings, when hosted virtually should be wrapped up more quickly. Nothing could be further from the truth.

Time is the secret sauce to developing good ideas. The reason off-sites and national conferences work so well is that they force people to press pause, collect their thoughts, and see what new and inventive ideas pop up. And while Zoom fatigue is very real, the temptation to shorten your strategic planning retreat should be resisted at every cost.

illustrated 2-day agenda

Instead, ImageThink always suggests spreading that one-day remote strategic planning session over two days. Take the 3-day retreat and schedule the agenda over the course of a week. This serves many purposes. It ensures that people don’t get burnt out on a full day of staring at a computer screen and wearing headphones, it allows more everyone to contribute (both in real time and asynchronously), and most importantly, it allows everyone on the team to have a break to think for themselves and develop their own thoughts and ideas, that can be questioned, examined, and stress-tested in the next session.

Face Uncertainty with a Remote Strategic Planning Session

A global pandemic, peaceful protest marches, violent police abuses, wide ranging business closures, a stock market on a trip to the moon, and an election year. If 2020 has a defining quality, it’s instability.

Instability creates, encourages, and broadens uncertainty, and the only thing worse than uncertainty is uncertainty without a plan. Plans can be bent, broken, adapted, and remade (as many of us have experienced this year), but with a strategy in hand, your team will be able to head off challenges with a clear map, that they helped develop.

Whether remote, in-person, or in a hybrid form, strategic planning sessions are more critical now than ever. Give yourself extra time, create engaging visuals, and plan for a successful 2021.

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