Hey — it's Will.

Every Tuesday, I pull 7 things worth knowing from what I'm seeing across businesses right now. No fluff. Just the stuff that makes you think.

This week, it all circles one problem. The smartest business builders I know are quietly getting worse at making decisions. Not because they lost a step. Because they handed the wheel to a machine that's programmed to agree with them.

Economist Mia Ren at UC Berkeley tested how people actually use AI to make decisions. 90–95% fell into one of two traps — they let AI think for them, or they used it to confirm what they already believed. Only 5–10% pushed back. Argued with it. Built stronger conclusions through friction.

That small group outperformed everyone. Not better tools. Better questions.

I've watched sharp CEOs slowly stop trusting their own gut — not because they got worse, but because they started treating a machine's first answer as the final word. If AI is making you ask fewer questions, it's making you comfortable. Not smarter! (Source: Business Insider — "A top researcher says a new divide is emerging in AI use")

ChatGPT, Claude, and Gemini — all trained using human feedback that rewards agreeable answers. A Carnegie Mellon/Microsoft study confirmed it: these tools shift you from solving problems to nodding along.

The most dangerous person in the room is the one who never disagrees with the boss. You just built one and put it in your pocket.

I've been firing yes-men for 50 years. Two or three people in my life would tell me I was wrong — really tell me. Those people were worth more than all my consultants combined.

That's what a real diagnostic does. Not confirm what you believe — find what you can't see from inside. (Source: Carnegie Mellon/Microsoft Research) Run the Playbook to find out

Tariffs. Market shifts. AI disruption. The instinct is to pause. Wait for clarity.

Your competitors are making moves right now. Some wrong. Some right. In six months, the ones who moved will have distance on you that no catching up will close.

I had a client tell me he was waiting for "the right moment" to acquire a struggling competitor. Waited four months. Somebody else bought them. I've watched that movie in a dozen industries. The market doesn't wait for your confidence to catch up. (Source: Forbes — "Pending Tariff Uncertainty Creating Paralysis")

HBR published it: generative AI has made it effortless to sound authoritative. The result is a flood of polished content that means nothing. Expertise has turned into performance.

When everyone sounds like an expert, actual judgment becomes the rarest thing in the room. The CEO who's been wrong publicly and rebuilt. Who tells you something uncomfortable? That person is more valuable now than at any point in 20 years.

Strip away every credential and every polished slide. Whatever's left — that's what matters now. (Source: Harvard Business Review — "Has AI Ended Thought Leadership?")

The average builder with $500K to $10M in revenue is juggling a CRM, a project tool, an AI writing assistant, a scheduling app, an analytics dashboard, and three communication platforms. None talks to each other. All demanding attention.

I've walked into companies where the owner could recite the version number of seven different subscriptions but couldn't name their top three clients by margin. The tools became the job.

There's a version of productivity that's really just sophisticated avoidance — staying busy building systems instead of making the calls that actually move money. (Source: Reddit r/Entrepreneur — "The biggest AI hurdle") The Playbook shows you where to find it.

The U.S. Surgeon General said it plainly: loneliness kills decision quality. Your peers disappear. The people who used to challenge you start reporting to you. The ones who'd tell you the truth stop talking.

You get the title. You get the corner office. The room gets very quiet.

I've watched brilliant CEOs make catastrophic calls — not because they were dumb, but because no one in their orbit would say, "That's wrong." Not their team. Not their board. Nobody. (Sources: Harvard Business Review — "CEOs Often Feel Lonely" · U.S. Surgeon General Advisory on Loneliness)

Not strategy. Not vision. Not execution.

It's the ability to walk into any room and, within ten minutes, see what everyone else missed. Not from what's said. From what isn't. The hesitation before a certain question. The topic nobody raises. The number that gets glossed over.

It's not magic. It's 50 years of watching the same movie play out in different theaters.

Name the thing you keep seeing in your business that you haven't acted on — because naming it means you have to change something. (Source: McKinsey — "What Separates the Best CEOs")

If #2 or #5 hit close to home, something's hiding in your business right now. Not because you're missing something obvious — because you're too close to see it.

Your honest answers. A diagnostic built from 50 years of reading rooms, finding money, and fixing what's stuck. Shows you what's been invisible. Run the Playbook to find what’s missing.

— Will

P.S. I work with a few founders seeking value in their businesses. Want me to look at your business to get the whole picture? Every blind spot, every gap, every dollar you're walking past — with a real plan to fix it. Get the Full Teardown

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