Stop Being a Strategic Thinker

In a world dominated by MBAs, leadership courses, and strategy retreats, we're taught to think in straight lines: set goals, build plans, execute directly. Clean, logical, safe and increasingly irrelevant. The leaders shaping the future aren't following the playbook; they're rewriting it. It's time to ditch strategic thinking and embrace the power of oblique contrarianism.

The Three Types of Thinkers: Only Two Win

• Strategic Thinker: Direct, logical, predictable, linear. They execute the same playbook everyone has, making them easily replaceable by AI.
• Oblique Thinker: Indirect, pursuing complex goals through unexpected, sideways paths. They reach destinations others miss by avoiding the obvious road.
• Contrarian Thinker: Counter-consensus, spotting opportunities where others see risk. They zig when the market zags, moving when crowds freeze.

AI excels at straight-line strategies mexecuting plans and analyzing data faster than humans. But it can't think sideways, challenge assumptions, or sense weak signals. That's your irreplaceable edge.

The Paradox of Obliquity: Hitting Targets Indirectly

Economist John Kay calls it "Obliquity": the most complex goals are achieved indirectly. Profit-obsessed companies aren't the most profitable; innovative products defy market research; successful leaders lack detailed plans. Oblique paths lead to breakthroughs by embracing complexity and unpredictability.

History's Oblique Contrarians

• Winston Churchill (1940): No victory roadmap just oblique moves toward a direction. Objective achieved.
• Steve Jobs: Ignored focus groups, built what markets didn't know they needed. Pure contrarian genius.
• Amazon: Chased customer obsession for 20 years, not profit. Became the world's most profitable company.

None were strategic thinkers; all were oblique contrarians.

Your Unfair Advantage in the Age of AI

AI handles execution and optimization, but it can't question assumptions, feel hidden signals, or choose sideways paths. With 86% of leaders craving content that challenges them (Edelman, 2025), oblique thinking is your last human superpower.

Building Oblique Leaders at Crowe

At Crowe Pioneering & Excellence, we don't just refine plans we cultivate oblique leaders. We train pattern sensing over data hoarding, indirect strategies over direct execution, and assumption-breaking over best practices. We build courage for unmapped paths, helping organizations dominate through contrarian boldness.

Most reward strategic thinkers; dominators celebrate oblique contrarians. Which does your culture celebrate? Like the chess knight moving in L shapes, not lines embrace obliquity. It's the dangerous piece that wins the game. Are you thinking obliquely enough?

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