Stratagem Weekly

Strategic playbook tackles “Wicked’ problems

Given the "wicked" problems businesses, government and society face, everyone should know how to be a more effective problem solver.

It was my great privilege in early 2024 to provide a workshop and strategic playbook on problem solving for this year’s class of Leadership Greater Madison. (To see examples of my tailored strategic planning playbooks, visit my website.)

The workshop covered skills spanning critical thinking, cost-benefit analysis, and strategic planning. I folded in concepts from a book I greatly admire, “Cost-Benefit Analysis: Concepts and Practice” by Anthony Boardman, David Greenberg, Aidan Vining and David Weimer. I used many tenets of strategy I’ve learned the past 15 years from my friend Roger Martin.

For example: It’s not enough to suggest a good idea that just might solve a problem. Any idea can only be assessed in the context of comparison to the cost/benefit of alternatives, be it the status quo or a second or third good idea.

This requires aligning people beforehand on what defines a cost, a benefit, and how to objectively research each. Without this, the perspectives of any possible solution are vulnerable to prejudice (for or against) that aren’t even conscious for most people. So, teams tackling the problem will find it difficult to align. Plans will not be as effective as they could be.

Planning to resolve a problem, and strategic planning to resolve a problem, are not the same: The latter searches for a strategy that overcomes several barriers to problem resolution "in one fell swoop." To achieve this, planners must grapple with tough realities, costs, and tradeoffs. But the result is a strategic planning playbook with metrics, tactics and people all focused to deliver what’s required to successfully resolve the problem!

In contrast, typical plans are driven by dreams of how leaders would like things to be—wishful activities that never get completed; spreadsheets and promises built on hope.

Yet hope is not a strategy.

What is?

In the face of today’s wicked challenges (such as shortages of childcare, low-income housing, and skilled workers), it’s training community volunteers, activists, elected officials and appointees on how to be a more strategic and effective problem solvers.

The cost of earnest people not getting skills in this is huge.

The benefit of their eyes being opened by even a short course?


For more, visit my website or follow me on LinkedIn.

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