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AI strategy for executives who are still human. Each issue gives you one framework, one kill criterion, or one scar with the lesson attached.
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Tags: ai strategy
Showing 12 results:
#028 - Your AI Committee Can Discuss. One Person Must Decide.
Thursday, 16:20.
An AI model starts sending bad recommendations.
The steering committee meets on Monday.
The governance chart says, “The committee owns the decision.”
The operating team now has two bad options: wait four days while the problem continues, or act without authority.
On the op...
Aug 01, 2026
ai governance
ai strategy
executive decision-making
#026 - What has to stop for this to start?
Can you have two girlfriends at the same time?
Technically, perhaps.
Ethically, not in my world.
Practically, it usually ends in disaster.
Not because two is a difficult number, just because both relationships compete for the same finite resources: attention, time, care, and energy.
A serious r...
Jul 18, 2026
ai strategy
executive decision-making
prioritization & focus
#024 - You're In Love With the Idea of AI.
I dated a woman who fell in love with a man I'd never met.
He had my name. My voice. My address. But when she described him to her friends, I didn't recognize him. The accomplishments rearranged. The future she'd already written for us. A version of me she'd carefully composed.
She wasn't lying. ...
May 17, 2026
ai strategy
executive decision-making
leadership psychology
#023 - I Owe You an Update. The Timeline Changed.
I have my routines that make me strong. Or stronger.
Exercising every day. Taking a walk in my forest. Reading. Meditating. Learning.
They are not impressive. They are not optimized. They are not hacks. They are the small, repeatable things that hold a person together when the world keeps changin...
Apr 25, 2026
ai strategy
future of ai
leadership psychology
#022 - AI Is Like Your Boyfriend. Genius and Idiot, Sometimes.
He solves a Rubik's Cube in one minute. Then he forgets your mother's name. Again.
He explains quantum entanglement to your dad at dinner. Then you tell him — for the third time this week — that your sister is coming on Saturday. He nods. He smiles. Saturday arrives. He has no idea why she's stan...
Apr 19, 2026
ai risk & compliance
ai strategy
human-ai collaboration
#020 - Stop Diagnosing. Start Building.
I was thinking recently about the beautiful journey of building a family from a romantic relationship.
It's an adventure filled with discovery. Yes, there are twists and turns, but that's what makes it real. You bring different strengths to the table. You carry stories from your past that shaped ...
Jan 24, 2026
ai strategy
executive decision-making
future of ai
#019 - The Art of Subtraction.
We all know the saying: "Sometimes less is more." It resonates deeply with me, but it took me years to understand why.
I have a default setting: over-responsibility, especially with loved ones. I tend to think about their needs before they do. I plan for them. I try to predict what they want, oft...
Jan 11, 2026
ai strategy
leadership psychology
prioritization & focus
#017 - Target the Moon.
In the boardroom of 2025, the most dangerous phrase you can hear is: "Let's just start with the low-hanging fruit".
It sounds sensible. It sounds lean. In reality, it is a sedative. We are currently caught in a global "Short-termism" trap, a psychological and economic glitch where we prioritize i...
Dec 21, 2025
ai strategy
executive decision-making
future of ai
#011 - Return on Intelligence.
Your CFO asked for the ROI on that AI project.
You sent her a spreadsheet showing $300K in annual savings.
She approved it.
You just made a $3 million mistake.
The Courage Part
Here's what most executives won't tell you: measuring AI on cost savings alone is career suicide.
Not because the savi...
Nov 09, 2025
ai strategy
case study
executive decision-making
#009 - Delay is a Decision.
Most executive AI strategies are built on a dangerous illusion.
The illusion of participation.
You run pilots. You fund experiments. You brief the board on "your AI journey." You feel you are in the game.
You are confusing activity with progress.
I see this every day. Confident leaders sliding to...
Oct 25, 2025
ai strategy
future of ai
prioritization & focus
#007 - The Year You Started Cloning Yourself.
The conversation around AI in the executive suite has become predictable, and frankly, a little boring. We're told AI is a hyper-efficient assistant that can summarize meetings, clear our inboxes, and draft emails. These are fine, but they are tactical efficiencies. It's using a supercomputer to ...
Oct 11, 2025
ai strategy
future of ai
human-ai collaboration
#005 - Strategy is for amateurs.
Strategy is for amateurs. Execution is for professionals.
Not quite.
You have the credentials. Great university. Real experience. You enjoy strategy and you’re good at it. Yet your plans stall. The deck is sharp, the meetings are smooth, but the results… thin. Easy to blame company culture, headq...
Sep 27, 2025
ai strategy
change management
prioritization & focus
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