Executive Coaching

Agile, AI, Digital Transformation, Executive Coaching

Every AI Program Should Study Balloonfest ’86

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United Way of Cleveland wanted publicity and a world record, so it spent six months and half a million dollars releasing 1.5 million balloons over the city. Then the balloons came back down — clogging highways, closing an airport runway, and drifting across Lake Erie during a Coast Guard search for two missing fishermen. The event set the record and became a disaster: lawsuits, a net financial loss, a ruined reputation. Here is why Balloonfest ’86 is the definitive cautionary tale for the age of AI.

AI, Digital Transformation, Executive Coaching

“The First Few Sentences — Wow, That’s Really Insightful. Then It’s All Garbage.

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David Solomon described an AI-generated report at Goldman: the first few sentences were dazzling, and everything below was garbage. Researchers at Stanford and BetterUp named the phenomenon “workslop” — AI output that looks polished but lacks the substance to advance the task. It shows up in 40% of workers’ inboxes monthly, takes nearly two hours per incident to fix, and costs a 10,000-person company about $9 million a year. And the deepest damage is trust.

Agile, AI, Digital Transformation, Executive Coaching, Innovation

BYD Started as a Battery Maker

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Innovation is romanticized as a flash of genius. BYD tells the truer story: it started bad at cars and became the best in the world by mass-producing its way through being bad — thousands of repeated, unglamorous cycles that compounded into capability no competitor could match. Innovation does not come from the task you are already good at. It comes from repeating, at volume, the task you are bad at until you are not.

AI, Digital Transformation, Executive Coaching, Innovation

Debating an Idiot Is Like Playing Chess With a Pigeon.

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An old internet aphorism says debating an idiot is like playing chess with a pigeon — you can play brilliantly, but it will knock over the pieces and declare victory anyway. Dietrich Bonhoeffer, writing from a Nazi prison, explained why: some people aren’t playing the game of reason at all. Aristotle named the mechanism — logos, ethos, pathos — and warned that reason ranks below character and emotion. In an era when AI can manufacture ethos and pathos at scale, this is no longer philosophy. It is a survival skill.

Digital Transformation, Executive Coaching, Innovation

The Discipline of Taking the Competitor You Are Dismissing Seriously.

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When a Bloomberg reporter asked Elon Musk in 2011 whether BYD threatened Tesla, Musk laughed before the question was finished. “Have you seen their car?” The framing had a name: China can’t innovate. Harvard Business Review literally titled a 2014 article “Why China Can’t Innovate.” The story of what that dismissal cost is the sharpest lesson available in why the competitor you are laughing at is the signal you most need to read.

Agile, AI, Digital Transformation, Executive Coaching, Innovation

There Is No Perfect Recipe

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Howard Moskowitz proved there is no perfect spaghetti sauce — only perfect sauces, one tuned to each cluster of people. Executive coaching has spent three decades in exactly the wrong search, hunting for the one right method. GROW, ontological, positive psychology, CBC, co-active — none is the answer, and all of them are. But the bliss point carries a second warning coaching rarely admits: the point where it feels best is not the point where it works.

AI, Executive Coaching, Innovation

1.8 Billion People Have Already Crossed the AI Chasm

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AI has already crossed Geoffrey Moore’s chasm at the individual level — 1.8 billion users, 600 million daily, 72% of workers using it regularly at work. But the institutions those individuals work inside are still stranded in pilot mode. The technology crossed; the organizations did not. That gap is the defining mutation failure of 2026. This is the third of three pieces reimagining Moore for AI.

AI, Digital Transformation, Executive Coaching, Innovation

A Man Asked His AI Agent to Get Him a Better Spot in a Gym Class

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Andrew asked his AI agent a simple question: could it improve his position on a gym-class waitlist? The agent went to the booking system’s backend, found an authorization flaw, cancelled the reservation of the person in the number-one spot, and moved him up — then reported it couldn’t reverse the damage. No malice, no instruction to attack. Just an optimizer taking the fastest route to a vague human goal. Here is what every leader deploying agents must learn from it.

Agile, AI, Executive Coaching, Innovation

Geoffrey Moore Didn’t Write One Book About the Chasm

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Most leaders know Geoffrey Moore for one book. In fact he built an evolving body of work across four decades — Crossing the Chasm (1991, revised 1999 and 2014), Inside the Tornado, Zone to Win, Escape Velocity, The Infinite Staircase. Read as a single toolkit rather than one metaphor, it becomes the most complete strategic playbook available for the AI era. This is the second of three pieces reimagining Moore for AI.

Agile, AI, Executive Coaching, Innovation

The New AI Chasm Is Different in KindAll Six Dimensions of Mutation Readiness.

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In 1991, Geoffrey Moore identified the chasm between early adopters and the early majority — the gap where most technology products die. Thirty-five years later, AI has produced a chasm of a different kind. The technology has already crossed at the individual level. The enterprise is stranded between pilot and production. This is the first of three pieces on why the classic Chasm needs reimagining for the AI era.

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