Why the smartest people are the hardest to help?

“If you're very, very stupid, how can you possibly realize that you're very, very stupid? You'd have to be relatively intelligent to realize how stupid you are.” - John Cleese

This quote makes me laugh - and then sigh deeply. Because I’ve lived it.

As a senior project management consultant and trainer, I’ve had the privilege of working with bright, ambitious, high-powered leadership teams. They're smart - sometimes brilliant. And yet, these same brilliant minds are often shockingly resistant to expert advice.

When Expertise Meets Executive Overconfidence

Despite years of project management experience, certifications, methodologies, and case studies, I sometimes find myself completely unable to convince top managers that they’re heading straight into avoidable failure.

They nod politely, thank me for the insights - and then charge ahead, ignoring every warning. It’s not that they’re malicious. Or even irrational. It’s that many successful people start to mistake success for infallibility.

Enter: The Dunning-Kruger Effect

The John Cleese quote isn’t just comedy - it’s a paraphrased version of the Dunning-Kruger effect: The less competent someone is in a subject, the more likely they are to overestimate their ability. And ironically, the smarter someone is in their own domain, the more likely they are to think they’re experts in yours too.

“Project governance? Risk modeling? That’s just common sense, right?” No. It’s not. But thank you for your confidence.

When Advice Becomes Inconvenient

Here’s the real kicker: Even when they do sense something’s off, many leaders will choose to double down on their existing habits rather than rethink their approach. Why?

• Because slowing down looks like weakness.

• Because admitting blind spots feels risky.

• Because “we’ve always done it this way” is a comforting illusion.

So What Do We Do?

We consultants adapt. We stop preaching and start facilitating. We reframe advice as risk management, not criticism. We use stories, tools, benchmarks - whatever helps create a mirror without triggering defensiveness.

And when that doesn’t work? We document everything... Because sometimes we’re brought back in a few months later to clean up the mess we warned them about.

Final Thought

I’ll keep trying. I’ll keep believing that smart people can be helped - if the timing, framing, and mood alignment stars all magically align. But deep down, I’m prepared. Because the smarter they are, the harder they are to help.

And if all else fails... I’ll just quote John Cleese again and send the invoice.