Planning Ahead and Expecting the Unexpected

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I love a good oxymoron:

  • Planning for uncertainty
  • Staying together alone
  • Choosing the best worst-case scenario
  • Creating clarity in crisis
  • Letting go as a means of gaining control
  • Strength through vulnerability
  • Favorite mistakes

Antithetical things, when linked, can spark new insight or breakthrough thinking.

F. Scott Fitzgerald said,

“The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.”

This idea pretty much sums up what leadership has become since COVID – and may forever be. Thus, leaders must embrace moving forward with an expectation of uncertainty.

So, how does one do that? These strategic planning steps will get you started.

Consider your purpose and core values.

Why do you do what you? What gets you up in the morning even when things are hard? How do you make the world a better place? What enduring values define your culture?

Engage in a “now and later” thinking.

  • Now – Review your data: financials, external market trends, engagement data, DEI data, customer data. Create a shared understanding of your current state.
  • Later – Imagine the future. Given your purpose and current reality, what is possible? What opportunities exist? What threats loom large.

Clarify your unique competitive advantage.

What do you do better than your competitors or is impossible for others to copy? What drives customer loyalty? How might you best leverage your strengths and lean into opportunities? What if you focused on being different instead of being better? Could you focus on finding different and better?

Create an operating plan.

Once you have a vision for the future, ask how you will get there in the near-term. What milestones and metrics will mark your progress along the way if things go smoothly? How will you track progress and report performance against benchmarks?

Contemplate the worst-case scenario.

Test your operating plan against all the “what-ifs” you can think of and identify strategies for risk mitigation and/or crisis management. Engage in second-order thinking to uncover unintended consequences that could occur.

Moving forward with a plan doesn’t mean you have it all figured out. It means you have clarity about where you are, where you hope to go, how you will get there, and what you will do when (not if) curve balls come your way.

It means you can function in the dysfunction.  

Good luck, and let us know if we can help! You don’t have to do it alone.


For more on strategic planning, read “Leading Blindfolded: The Importance of Data.”

And, don’t miss our upcoming webinar, “Moving Forward: Restarting Your Growth Engine” on September 22, 2020 at 10:00 am ET.