How to Use AI to Uncover Cognitive Blind Spots and Challenge Your Assumptions

The Hidden Trap: How We Build False Cause-and-Effect Connections

Humans are wired to seek comfort and safety. Whenever we’re working on something, we need all the cause-and-effect relationships to be clearly mapped out — everything must have a rational explanation. And if those connections don’t actually exist, we construct them anyway. Almost always unconsciously. And by the time you realize it, it’s already too late. The train has left the station.

What’s missing is challenge.

Cognitive Blind Spots and the Questions That Expose Them

Nassim Taleb, in The Black Swan, recommends constantly asking: what don’t we know?
David Rock’s neuroscience research suggests asking: what if?
And even Artemy Lebedev — in his own blunt way — proposes asking: am I even doing the right thing here?

At our strategy sessions, we dedicate a specific block to challenging and double-checking: what have we overlooked?

Using AI to Surface What You’re Missing in Real Time

But how do you keep asking these questions when you’re buried in day-to-day operations?

Here’s a practical lifehack: ask your GPT to make it a habit — whenever you discuss any project with it, it must always challenge you and find an answer to the question: what don’t I know, or what have I missed?

Be prepared to take off the rose-tinted glasses. The blinders come off too.

Survivorship Bias: The Cognitive Blind Spot You’ll Finally Start Seeing

You’ll also inevitably revisit the Survivorship Bias model — Taleb’s framework you thought you already knew. Because now you’ll start experiencing it firsthand, in full, and on a regular basis.

And that’s when you’ll see the parallel reality.