Retreat to Advance: Using Your Offsite Meeting to Focus on the Future


The pandemic may have obsoleted the traditional strategic planning process, but what are you and your organization doing to replace it? Many organizations have yet to devise a new approach suitable to the VUCA (volatile, uncertain, complex, and ambiguous) future. Thus, now may be the right time to go about reinventing your early warning, innovation, and forward-thinking capabilities, while also updating your organization’s future vision to reflect post-pandemic realities.

One proven way to do this is to organize a retreat of your top people. Here, away from the isolation and daily pressures, you can collaboratively consider both a new plan and look at how you navigate in an uncertain and opportunity-filled environment. Inviting key strategists in your organization to come together in an elegant setting and to talk not about emergencies and contingencies, but about vision and focus, is money well spent. Designed well in advance, an offsite leadership retreat can become transformational in creating alignment for an organization. Use these six guidelines to steer your next retreat in a bold new direction:

  1. Use the offsite retreat to ask fundamental reset questions.

Asking questions is key to discovery — and to making progress. Especially questions that cause your team to consider how your strategic planning process fared during the crisis, and how you’re revitalizing planning in the post-pandemic environment. To get the creative juices flowing, ponder these key questions with your team:

  • Is our present planning process defunct, or is it still helping guide us into a more prosperous future?
  • How well did we do with contingency planning during the depths of the crisis? What did we learn from that experience?
  • How have we dealt with longer-term planning during the pandemic, and what did it reveal about the effectiveness of our process?
  • What new models of strategic planning out there might help us reinvent our own?
  • What are the most important workplace, demographic, consumer, technological, geopolitical, and social trends that we need greater insight into going forward?
  • How are our strategic foresight efforts linked to our innovation roadmap, and how do we create greater linkage and alignment?
  1. Use your retreat to ponder risk in the post-pandemic environment.

The pandemic unearthed a whole new dimension of risks that require upgrading of how an organization identifies and manages risk. In the context of the retreat, leaders will learn to use new tools to look for ways to size up and to mitigate the external and sometimes hidden risks the organization faces. But signaling a cautious attitude of avoiding risk and “playing it safe” can discourage innovation. Risk-taking will always be necessary, yet assessing risk is sometimes not communicated or understood. Avoiding risk as a matter of policy is equally dangerous in today’s hyper-competitive global environment. Instead, seek to simultaneously identify new opportunities and better manage the risks your organization needs to take to test new strategies and to find the future first.

  1. Use your retreat to “future proof” your organization.

No organization is completely “future proof,” because no organization is immune from sudden new threats from global pandemics, climate disasters, new technologies, and sudden economic downturns. But “future-proofing” is the process by which you monitor and respond to technological, competitive, and strategic shifts. The retreat can be used to conduct an audit on how well or how poorly your organization adjusted to Covid’s various crises, and to new technology and customer demands that occurred. Make sure to leave time to discuss ways your “Early Warning System” might be revamped for the fire next time.

  1. Use the leadership retreat to think farther ahead of the digital future.

No strategic plan is complete without a visionary technology mind expansion component.  Use the offsite to spark fresh thinking in this realm by posing such questions as: Are we thinking out far enough ahead on technology? Where might we enhance or transform our technology strategy going forward? What customer pain points do we need to take on before someone else beats us to the punch? And how will this technology, if we adopt it, deliver greater value to our customers?

  1. Use your offsite meeting to challenge industry and internal assumptions.

Assumptions act like barnacles on the side of a boat– they slow you down, or worse, cause you to miss out on seizing emerging opportunities. At a time when business models have shorter and shorter shelf lives, bringing assumptions to conscious awareness is a critical and ongoing first step to spawn strategic thinking. Retreats become transformational when executives and managers are freed from thinking only in their functional silos and are given license to consider opportunities and new approaches. Such meetings benefit from a neutral, outside facilitator to provide a process that encourages the group to wonder anew about the limiting beliefs, paradigms, unspoken rules, that the organization has long harbored, but has not recently revisited.

  1. Use the offsite gathering to focus on thinking beyond incremental innovation.

My multi-continent experience in speaking at and/or leading retreats suggests that management teams sometimes lack confidence that they can come up with and successfully execute bold ideas. But a well-designed strategic offsite is a learning experience and builds executive confidence in the all-important arena of innovation. Here, white space opportunities (those that arise between business units where nobody has clear jurisdiction) that were assumed to be beyond an organization’s capabilities suddenly become possibilities. New collaboration and idea-sharing gets fomented. The retreat becomes the vehicle to discover and open up to new possibilities, to identify new markets, and ultimately to profit from new revenue streams that aren’t even on the radar today.

In sum, the pandemic has laid bare the weaknesses of the traditional strategic planning process. But nothing has really come along to replace it, nor to reinvigorate it. Thus, there may never be a better time than right now to go about reinventing your early warning, innovation, and forward-thinking capabilities and updating your organization’s future vision. Inviting the key thinkers in your organization to retreat in order to advance could be the best move of all right now.