Wicked Problems Need a Second Kind of Leadership

Insightful Leadership Spots the Wave. Optionality Carries You Through the Breaks

Wicked problems don’t hold still long enough to be solved.

I’ve long argued Insightful Leadership is the answer. See the wave before it crests, ride it and get your business in position before the paradigm shift hits.

It is, partially.

While spotting a wave tells you it’s coming, it doesn’t tell you what to do when the wave changes shape halfway through the ride. And wicked problems, like waves, change shape constantly.

Insightful Leadership alone isn’t enough. Leaders must pair insights with their natural partner – optionality.

Wicked Problems Won’t Sit Still

Horst Rittel and Melvin Webber, two Cal-Berkeley professors of design and urban planning, defined the term in a 1973 paper in Policy Sciences. Wicked problems, they wrote, are novel. They resist solutions because their requirements are incomplete, contradictory and constantly shifting.

Wicked problems share a few nasty traits. Rittel and Webber coined the phrase “no stopping rule” – you never get a clean signal that you’re done. They have no true-or-false test – solutions aren’t right or wrong, only better or worse.

And trial and error doesn’t yield solutions either – every attempt changes the conditions of the wicked problem. So you essentially have a new problem and can’t just try again.

You can’t even fully define the problem until you’ve tried to solve it, and by then the problem has usually moved.

That’s a precise description of what executives are living through right now. Over the last few years, every time a company seems to have tariffs figured out, the import taxes change. In an instant, politicians rip up trade deals once deemed sacrosanct.

Seventy-two percent of trade professionals now name U.S. tariff volatility their top regulatory concern, up from 41% a year ago, according to Thomson Reuters’ 2026 Global Trade Report.

Compare that to a normal hard problem. A hard problem, like optimizing a delivery route, has a right answer you can find with enough data. A wicked problem has no right answer, only better or worse responses that keep expiring.

How Insightful Leaders See Around Corners

Insightful Leadership is a discipline, not intuition. Every wave starts as a signal too faint for most people to notice. Watch for weak signals before they harden into consensus, then act while everyone else is still debating whether the signal is real.

In September 2000, Netflix co-founders Reed Hastings and Marc Randolph flew to Blockbuster’s Dallas headquarters and offered to sell their struggling DVD-by-mail startup for $50 million. Blockbuster passed. A decade later, Blockbuster filed for bankruptcy. Netflix’s market value today tops $300 billion.

Blockbuster wasn’t run by fools. It had 9,000 stores and $6 billion in annual revenue. Its leadership was optimizing a real, profitable business. But they were solving yesterday’s problem – how to get more customers into more stores.

Netflix’s founders were asking a different question: what happens once bandwidth stops being the bottleneck? Insightful Leaders ask that second kind of question while the first kind is still working.

That’s the muscle wicked problems demand. Not “how do we run the supply chain we have?” but “which of the assumptions holding it together won’t survive the next disruption?”

Seeing the Wave Coming Doesn’t Mean You Won’t Drown

Executives who read the China tariffs correctly in 2018 did the smart thing. They moved production to Mexico. That’s Insightful Leadership working exactly as designed – they spotted the wave, reoriented before the paradigm shift and avoided the first tariff hit entirely.

Then the wave changed shape.

In March 2025, Washington slapped a 25% tariff on Mexican imports under emergency powers. The Supreme Court struck that down in February 2026. So for 11 months, anyone who bet everything on a single new supply chain built around Mexico suffered.

Even after the ruling, the Trump administration imposed a new 10% surcharge within days, although the Trade Act of 1974 limited its duration to 150 days.

Mexico moved too, raising tariffs as high as 50% on thousands of product categories from countries without a Mexican trade deal. President Claudia Sheinbaum said the goal was to boost domestic production and address trade imbalances. But trade analysts saw the tariffs as a way to close the “back door” manufacturers used to route Chinese components through Mexico.

None of this means Insightful Leadership failed. Everyone who saw the China tariffs coming and moved was right.

But being right about the first wave doesn’t protect you from the second. Wicked problems don’t wait for you to finish solving them before they mutate into a new version of themselves. You solve for the requirements you can see. By the time you’ve implemented the fix, the requirements have moved again.

Seeing the wave is necessary. Insight just isn’t sufficient. What these companies needed wasn’t a better read on where the wave was heading. They needed a second board.

The Board You Keep Waxed

Optionality is not a backup plan. A backup plan is what you pull out after Plan A fails. Optionality means you never had just one plan running.

Look back at the companies that moved from China to Mexico. Most treated the move as a finish line: new country, new contracts, new steady state. That’s where most companies stopped, and it’s why the second tariff wave caught them flat-footed.

Being in Mexico wasn’t enough on its own. The tariffs Washington imposed on Mexican imports exempted goods that qualify under USMCA rules of origin.

The companies that came through both waves clean didn’t just pick the right country. They kept documenting the bill of materials and meeting regional content thresholds after they made the move.

Consequently, Mexican exports qualifying for USMCA preferential treatment climbed from under 45% in January 2025 to nearly 90% by year’s end, according to U.S. Department of Commerce data.

Manufacturers who treated that qualification as ongoing work, not a box checked once, ended up holding the one asset that survived every version of the tariff fight.

That’s optionality doing its actual job. Insightful Leaders must go beyond picking the right option. They must build the standing capacity to redirect every time the requirements move again. Optionality means keeping a second board waxed and ready to go.

Insight Watches. Optionality Moves.

Don’t mistake this for a two-step process. See the wave, then build your options. That’s not how it works, because wicked problems don’t wait for you to finish step one.

Insightful Leadership and optionality run at the same time, doing different jobs.

Insight tells you where to look. Optionality gives you something to do once you’re looking. Drop either one and the other stops working.

Insight without optionality is just a good view of the wave that’s about to hit you. Optionality without insight is a warehouse full of boards you never use to surf, because you never saw a reason to move.

That’s the real lesson underneath the tariff story. The executives who read the China tariffs correctly in 2018 had the insight. The ones who kept requalifying for USMCA after the move was “finished” had the optionality. Surfing both tariff waves took leaders running both jobs at once, not one after the other.

Wicked Problems Don’t Offer a Finish Line

I don’t have a permanent solution to your wicked problem. Nobody does – that’s what makes it wicked. What I have is a proven pair: the insight to see the wave and the optionality to survive it changing shape. Building both into how you lead is the work.

What wicked problem is keeping you up at night? I’d love to hear how you’re building your own second board. Drop me a line.

 

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