Dr. No #50 - Dr. No – 11 Ways Daniel Kahneman Will Mess With Your Thinking (In the Best Way Possible)

Hey lawyer,

Rosa and I just re-listened to one of our all-time favourite thinkers — Daniel Kahneman — in a masterclass interview with Shane Parrish.
It’s one of those “pause every five minutes and rethink your life” conversations.

Here’s what smart GCs can steal from it:

1. Food for Thought

What’s the one decision on your desk right now…
…that you think you’re making rationally, but is actually just confirming your first impression?

2. Book Insight – 5 GC-Adapted Kahneman Lessons

1. Delay Your Intuition
Israeli army interviews used to run on gut feelings — and failed. Kahneman forced interviewers to score six traits first, then make a call. Accuracy soared.
GC takeaway: Make your team score facts before they “just know” whether to approve or block a deal.

2. Loss Aversion
People fight harder to keep a perk than to win a new one.
GC takeaway: Once you give your business team a contract shortcut, rolling it back will feel like a human rights violation.

3. Your Rules Become Your Defaults
Kahneman’s rule: never say “yes” on the phone. Saved him from regret.
GC takeaway: Create “never rules” for your own work — e.g., never approve high-risk clauses without a second review.

4. Behavior Is Situation, Not Personality
Even saints snap under pressure. Change the environment, change the behaviour.
GC takeaway: If a business unit is “difficult”, fix the incentives, not the people.

5. Legitimize Doubt
Use the “premortem”: “It’s two years later, our decision was a disaster. What went wrong?”
GC takeaway: Make this mandatory before greenlighting major litigation, deals, or restructures.

3. Mental Model – The Premortem Principle (Munger-style)

Don’t just think about why your plan will work.
Force yourself (and your smartest people) to imagine why it failed spectacularly.
It’s not negativity. It’s cheap insurance.

4. AI Booster – Comet

Perplexity’s AI browser on steroids. Research, summarise, and cross-check without falling into Google’s clickbait trap.
Perfect for GCs researching multi-jurisdictional compliance — or finding the one line in a 200-page policy that actually matters.

5. Quote to Reflect

“The best way to make a good decision is to imagine you already made a bad one.” – Daniel Kahneman

P.S.
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Stay cool,

Rosa & Manuel