Your Best Quarter Is the Warning
Why your AI dashboard looking healthy might be the most dangerous moment your company faces.
Read →Essays
How AI is changing leadership and strategy.
Long-form essays for leaders who would rather think than react. Drawn from ThinkRoom conversations and the patterns that surface in the work.
38 essays. Originally published on grail.works.
I Run a Strategy Firm. I Don't Have a Strategy.
A confession from someone who sells the one thing he can't seem to keep in stock.
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You Are Reading the Wrong Room
The data senior leaders use to make their biggest decisions is structurally biased. And the silent majority isn't where you think it is.
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The Skills That Survived
In which researchers pit AI against senior leaders and the wrong side wins.
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The Only Asset AI Can't Build
Your AI strategy is sending your employees a message about what you believe humans are for. Most companies have no idea what it says.
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Engineers Went First. You're Not Far Behind.
What software teams learned about AI that every profession will learn the hard way.
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The "Human-Centric AI" Lie, and the End of Homo Sapiens
Let me actually define what "human" means in the context of 'Human Centric AI'.
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A Jobs-Survival Guide for the Already Doomed
In which AI comes for your job and finds it defended by confusion, inertia, and a mortgage.
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The Dumbest Strategy in the Room
When I asked about his strategy, he said three words. "Beat last year." I waited for the rest. There was no rest.
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Good Is Where Great Goes to Die
The hardest prison to escape is not a bad life. It's a good one.
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The Nerd Principle
There's a difference between eliminating waste and destroying the conditions for mastery.
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Tantric Lessons for CEOs in the Age of AI
What ancient wisdom about polarity work reveals about why your organization feels dead.
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Build Builders, Not Users
The biggest bottleneck in business is shifting. From 'Who can build it?' to 'Who knows what to build?'
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Your Consulting Firm Just Hired a Country of Geniuses
My bet on what consulting becomes when analysis stops being scarce.
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When Bubbles Build Civilization
Every civilization-grade technology shift in the past 500 years has been both a speculative bubble and a genuine transformation. At the same time. The bubble funds the revolution.
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Your Org Chart Is From 1855. Your AI Is From 2025
When your AI-augmented employees become too fast for the company they work in.
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Your Bookstore Doesn't Need a Website
"You cannot have a strategic discussion about how AI impacts your business unless you have a fundamental understanding of AI." Not expert-level knowledge. Just enough literacy to see what's possible.
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You're Reading the Wrong Curve
Why your AI investments look disappointing when you're doing everything right.
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The Secret Every CEO Should Steal from Homer
How a 3,000-year-old poem explains why your PowerPoint isn't working.
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The ROI Paradox: How Chasing Returns Destroys Returns
When everyone optimizes for the same metric simultaneously, the optimization itself becomes the constraint.
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The Curiosity Advantage: Why Not Knowing Is Your Superpower
I used to think calling someone "curious" was the ultimate compliment. Turns out I was onto something. Just not in the way I thought.
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Your Leadership Team Is Embarrassingly Behind on AI (And It's About to Cost You Everything)
If you're in a leadership position and you're not personally using AI for your actual work, you're not just behind. You're actively sabotaging your organization's future.
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You Don't Rise to Your Strategy
Everyone's doing their job well. No one's doing the company's job.
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The Slow Death of Strategy
"You simply cannot have intelligent strategic discussions about AI if you haven't personally experienced its capabilities."
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The Stone Age Brain Meets AI
"People intellectually understand AI can make them at least 30% more productive, but emotionally, their Stone Age brain tells them to wait until someone else has done it first."
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The AI Leadership Gap Is Already Ridiculous
"Those who've had their AI awakening and jumped on the train will be in a completely different place by the end of the year than those who haven't. It will be noticeable. It will be felt."
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The Dangerous Obsession with Measurement
What if, in our rush to measure everything, we're actually understanding less?
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THIS IS KILLING YOUR COMPANY
"Can I tell you something I've never admitted to anyone? I have no idea what innovation actually means anymore."
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Why AI might force you to become more human
What if our relentless drive to break everything into processes, the very foundation of modern professional life, is about to hit its limit? And what if the path forward is a return to something much older?
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Why Every Business Is Now a Tech Business
"We need to go in this direction. I don't know how long it will take or how much it will cost."
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You’re too nice to have a strategy (so you don’t!)
"Strategy is a dictatorial game," he said. "It's for an autocratic, frankly kind of assholish leader." I nearly choked on my coffee.
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