How to Tell When AI Is Guessing (And Why That Matters)

Because even the Cheshire Cat grins when he’s bluffing.

The Cheshire Cat once told Alice he could vanish and still be right.

That’s confidence — and it sounds a lot like modern AI.

AI speaks with elegance, speed, and conviction.

But sometimes, behind the grin, it’s guessing.

Learning to spot that difference turns you from user into partner.

Step 1 — Watch for the Wobble

When AI is sure, its tone is crisp.

When it’s unsure, sentences stretch like taffy — extra qualifiers, softer verbs, sudden politeness.

“It’s likely that …”

“There may be some instances where …”

That’s your grin without the cat.

What to do:

When the language hedges, double-check it. Ask,

“How confident are you in that answer from 0 to 100 and why?”

Every founder needs a radar for false certainty — this one tunes yours.

Step 2 — Ask for Receipts

Truth leaves breadcrumbs. Guessing leaves perfume.

“Cite your sources or explain how you know this.”

If it produces clear reasoning, you’re grounded.

If it hand-waves (“based on general knowledge”), that’s fantasy.

Pro Tip:

Ask for two independent explanations of the same answer.

If they disagree, you’ve caught the grin in motion.

In pitch meetings or product claims, this same habit keeps you from quoting fiction as fact.

Step 3 — The Mad Hatter Challenge

Invite contradiction on purpose.

“Now argue the opposite as if you believed it completely.”

If both sides sound equally certain, you’re in the realm of improv, not insight.

Confidence ≠ accuracy; it’s just well-formatted courage.

If both arguments sound perfect, you’ve uncovered an untested assumption — not a paradox.

Step 4 — The White Queen Proof

Remember how she believed six impossible things before breakfast?

Use that optimism wisely:

“List the assumptions that would have to be true for your answer to hold.”

Real logic exposes its scaffolding.

A guess hides it.

That list of assumptions doubles as your investor due-diligence checklist — the foundations you must actually verify.

Step 5 — Run the Reality Clock

Finally, ask:

“When was this information last verified in the real world?”

AI memory is static; reality moves.

If time matters — markets, tech, politics — check the clock before quoting the cat.

Facts age like milk, not wine; freshness belongs in your footnotes.

Why This Matters

Good leaders don’t just want answers — they want accuracy with accountability.

AI can amplify your brilliance or automate your blind spots.

The difference is discernment.

Trust the tool that admits uncertainty.

It’s the digital equivalent of humility — and humility scales beautifully.

The Takeaway

In Wonderland, everyone speaks in riddles.

In business, you can’t afford to.

So learn to spot when your machine is smiling too wide.

The smartest question isn’t “Are you right?” — it’s “How do you know?”

Ask CoPilot today:

“Explain how you arrived at that answer, and tell me your confidence level.”

When you start measuring certainty, you stop chasing shadows.