I used to think the insight was the hard part. Turns out, insight is the easy part now. The cheap part. The part AI does before breakfast. You've seen the pattern. Brilliant strategy deck lands. Airtight logic. Crisp recommendations. "Expand into enterprise. Fix the pricing model. Rebuild

Good judgment isn't innate. It's calibrated. The difference between someone with good judgment and someone without isn't intelligence. It's feedback loops. Judgment compounds when you learn from what worked and what failed. Most people make decisions, see outcomes, and move on. They

You have a brilliant strategy. The analysis is solid. The logic is airtight. The deck is polished. Then you present it and nothing happens. Because you assumed stakeholders would align spontaneously. Alignment doesn't happen by accident. It happens in planned conviction moments. Most people think about stakeholder management

Good judgment is knowing what matters. It's distinguishing signal from noise. Seeing second-order effects. Understanding when rules apply and when they don't. You can have high intelligence and terrible judgment. You can ace every test and still make catastrophic decisions. Intelligence is processing power. Judgment is

2006. Steve Jobs approached Intel with an opportunity. Make the chips for a new product called the iPhone. Intel turned him down. The phones wouldn't sell enough to justify development costs. The decision you delay costs more than the decision you make. Intel didn't ignore mobile.

2008. MySpace was the world's largest social network. 115 million users. Then Facebook overtook them in April. What happened next wasn't gradual decline. It was a death spiral. We say growth and decline are opposites. Actually, they're the same mechanism running in reverse. MySpace

Everyone knows SpaceX fails fast. Blow up rockets. Learn. Iterate. What most don't know: How close it came to not working. 2006. Falcon 1 exploded 25 seconds after launch. Fuel leak. 2007. Second launch. Rocket tumbled out of control. Stage separation failure. 2008. Third launch. Collision during stage

Sears had a vision. One company, unified mission, customer-centric culture. Eddie Lampert had a better idea. 2005. He restructured Sears into 30 separate business units. Each with its own president, board, and P&L. Units would buy and sell services from each other through competitive bidding. Internal competition would

That quarterly strategy deck sitting in your shared drive? Beautiful vision. Market analysis. SWOT. Three-year roadmap with milestones. Can't tell you what decision to make Monday morning. We say strategy is the plan. Actually, strategy is the navigation. 1978. Honda and Yamaha went to war in the motorcycle

I've seen this so often. The comforting illusion that following processes equals strategic thinking. The difference between process and strategy determines whether your team merely executes or truly succeeds. Checklists get completed. Templates get filled. Meetings follow prescribed formats. You feel productive, methodical, even strategic. But something'

A few years back, I sat in a meeting where we were supposed to talk about... Strategy. We started by defining the word. As each person spoke, something felt off in a way I couldn't name. That's when I saw it: We were treating strategy like

Strategies don't fail because they're wrong. They fail because we treat them like monuments instead of gardens. We carve them in stone, present them in decks, print them in manuals. Perfect plans waiting for a perfect world. But look at how real progress happens: Small shifts

Picture this: An eager CEO stands before her team, delivering what she believes is the perfect announcement. Her slides sparkle. Her logic flows. Every head nods in agreement — those automatic, noncommittal nods that every leader has learned to fear. Three months later, she's pulling her hair out: "