Why Now Is Time For A Strategic Leadership Retreat

During the depths of the Global Pandemic, I began to notice a disturbing comment in the interviews I conduct regularly with organizational leaders. It went something like this: “We can’t even think about next week, much less next quarter. Strategic planning and forward thinking are out the window.”

It was an understandable sentiment. We were reeling, and there was no end in sight to the crisis. The prediction models were all wrong, the experts were as clueless as everybody else; the only thing certain was continuing uncertainty, so why even try to look or think ahead?

If you’ve been around for awhile, the comment was noticeable for the sheer fact that it was what disrupted companies were saying to themselves as they gently glided off a cliff. Blackberry, Sears, Blockbuster, and a host of other firms had tuned out the wider world and the trends, and circled the wagons. We’d all seen this movie before, and it didn’t end well.

If you’ve lived through recessions, terrorist attacks, stock market crashes and other natural disasters, you knew instinctively that those who take their eye off the ball often end up being thrown out of the game. You instinctively knew that the old adage “if you fail to plan, you plan to fail” was still valid, even amidst the chaos. This was supported in the business press almost on a daily basis as once-iconic brands like Neiman Marcus, Hertz, GMC, Chesapeake Energy and dozens of others filed for bankruptcy.

Maybe pandemics were just the latest type of disruption organizations and their leaders needed to contend with. But surely they did not signal the end of forward thinking and strategic innovation?

Right now, there’s another shift underway. Covid caseloads are falling fast, shots are going into arms, workers are returning to the workplace, consumers are spending, flights are full. There’s evidence of an economic boom that could dwarf anything we’ve seen in decades.

But the question is: Are you ready? Is your organization ready to pivot to faster growth?

Now is the perfect time to go about strengthening your management team’s forward thinking capability. It’s time to shape the next phase of your strategy.

One way to do this is to organize a strategic planning retreat. Designed well, an offsite leadership retreat can become transformational moments for an organization. Use these six guidelines to steer your next strategic retreat in a bold new direction:

1.  Use your offsite retreat to ask fundamental questions.

One trend I’m seeing right now is the need to focus on better managing risk. Covid unearthed a whole new dimension of risk that requires greater understanding and maybe even a redefinition of how you manage risk.

Leaders are looking for ways to mitigate the external and competitive risks their companies face. Yet they know that simply avoiding risk and “playing it safe” is not the solution in a hyper-competitive global environment, but can be the road to ruin. Instead, they seek to simultaneously identify new opportunities and better manage the risks their organizations need to take to find the future first.

Pose questions such as: How well did we do in responding to the Covid crisis? And how has the Pandemic changed our culture? How have our customers needs evolved? What’s important now? Just figuring out the right questions to pose at the meeting is helpful in promoting forward thinking.

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

“Future-proofing” is the process of avoiding technological, competitive and strategic blindsides. Use the meeting to conduct a debrief on how well or how poorly your organization adjusted to Covid’s technology and new customer demands, and discuss what ways your “Early Warning System” might be revamped for the fire next time.

3. Use the leadership retreat to think about the digital future.

No strategic plan is complete without a visionary technology component. Spark fresh thinking in this realm by posing such questions as: On balance, are we leading or lagging on technology? Where do we need to enhance or transform our technology strategy going forward? What customer problems do we need to take on? And how will this technology, if we adopt it, deliver greater value to our customers?

4.  Use your offsite meeting to assault industry and company assumptions.

Retreats become transformational when executives and managers are provided with a process to wonder anew about the assumptions the organization has long made about customers, markets, culture, the industry, etc. Assumptions act like barnacles on the side of a boat– they slow us down, or worse, cause us to miss out on emerging opportunities. In a time when today’s business model has a shorter and shorter shelf life, assaulting assumptions is a critical and ongoing necessity to strategic thinking.

5. Use the offsite gathering to focus on innovation execution.

My 30-year experience in the field of strategic foresight and innovation suggests that management teams often lack confidence that they can execute on bold ideas and are delighted when provided with a process that enables superior innovation capability. Many in the managerial ranks got there by being super-competent in their functional arenas. But they quietly see themselves as “fish out of water” when it comes to imagination, innovation, and vision. A well-designed strategic offsite builds executive team confidence.

6. Use the retreat to focus on white space opportunities.

If the rate of change outside your organization is faster than the rate of innovation inside your company, it’s time to take action. It’s time to figure out what needs accelerating. It’s time to shift from strategic planning (on an annual basis) to strategic thinking, which is ongoing, and needs to be part of the DNA. So-called “white space” opportunities are often assumed to be outside your organization’s walls, and outside its capabilities. But another way of defining them is to see them as those that fall between divisions, where no business unit has clear jurisdiction. Use your retreat to open up the white space of new possibilities, to identify new markets, and new revenue streams from existing capabilities.