Four kinds of CEO blind spots

After 25 years in the CEO seat and a few hundred coaching conversations since I sold my last company I've stopped asking CEOs the generic question "What are you not seeing?"

What I ask instead is more specific. There are four kinds of blind spots every CEO has. Most leaders can only see two of them, and the two they miss are usually the most expensive.

Here they are.

1. Filtered information. What your team is softening before it reaches you. Not lying, but filtering. The pipeline forecast that's always slightly optimistic. The team status that's always "in transition." The numbers presented in the way least likely to trigger a hard conversation. Nobody is hiding anything; they're just routing around your reactions.

The question to ask: "If my team had no fear of disappointing me, what would they tell me differently?"

2. Normalized patterns. The signals you've stopped processing because they've become "just how things are." The Tuesday meeting that always runs over. The same client objection that keeps coming up. The deal that's always going to close "next quarter." When something has been true for six months, it stops registering as data and you start making decisions around it instead of about it.

The question: "What's been true for 6+ months that I've stopped questioning?"

3. Outdated assumptions. Decisions you're still operating from, based on conditions that have since changed. A strategy you set two years ago when the market looked different. A pricing model from a competitive position that no longer exists. The original logic was sound. The world moved. You didn't.

The question: "What am I doing today because I decided it 18 months ago, and would I make the same call now?"

4. Behavioral blind spots. The hardest one. The way the company has built itself around you. Your reactions in meetings shape what people bring you. Your tone in tough conversations sets the ceiling for honesty. The parts of you that aren't serving the company well have become invisible to you - because nobody points them out anymore.

The question (this one usually requires asking someone else): "What is the company working around about me?"

Here's why this matters now.

Every one of these blind spots is a clarity problem. And clarity is the foundation of CEO transformation in the AI era.

AI is doing two things to CEOs right now. It's either overwhelming them with possibilities they can't process, or it's accelerating them faster in a direction they never clearly chose. Both failure modes have the same root cause: the role of CEO is changing in real time, and most leaders are still operating with assumptions formed before this shift began.

You can't transform what you can't see clearly. The four blind spots above are where most CEOs are losing visibility and AI is making it worse, not better, because every productivity tool you adopt accelerates whatever you're already doing. Including the wrong things.

This is the foundation of what I'm teaching live next Tuesday, May 5. "The CEO in the Age of AI".

We won't be covering the four blind spots in detail (you have them above). What we will cover is what comes after clarity. What it actually means to lead in this new environment, what's changing about the CEO role at a deeper level, and the framework I now use with my coaching clients to operate from a different position entirely.

60 minutes. Free. Live.