Dr. No - Issue #33 - How to make killer decisions (even when you don’t have all the facts)

“You can’t make decisions based on fear and the possibility of what might happen.” — Michelle Obama

Hey lawyer,

Welcome to this week’s issue of Dr. No — your 3-minute dose of brain fuel for legal leaders who think like strategists.

We keep it simple (and sharp) with our signature format:

• 1 Provocative Question to challenge assumptions

• 1 Insightful Book for strategic leadership

• 1 Mental Model (Munger, Buffett, Cialdini, etc.) to sharpen thinking

• 1 AI Tool for high-performance GCs

• 1 Quote to Reflect (edgy, elegant, or brainy)

This week’s topic?

How to make killer decisions when the crystal ball is foggy.

1 Question

If someone watched only your decisions this year (not the results), would they conclude you're world-class at what you do?

+ 1 Book Insight — Thinking in Bets by Annie Duke

Most of us judge decisions by outcomes. But great decision-makers do the opposite. They separate decision quality from result quality.

Because let’s face it — you can make the right call and still lose. (And vice versa.)

GC takeaway:
Start asking this question in every strategic meeting:

“What are the odds this goes as planned — and what’s the cost if it doesn’t?”

Annie Duke, a former poker pro, reminds us: bad outcomes don’t always mean bad decisions. Especially when you’re playing with partial information (which is… always).

Try this: Use “pre-mortems” with your team. Ask: “Let’s say this goes wrong — what did we miss?” It upgrades your risk radar in 5 minutes.

+ 1 Mental Model — Inversion (Charlie Munger)

Instead of asking “How do I make a great decision?”
Ask: “What would a dumb decision look like here — and how do I avoid it?”

Inversion is Munger’s trick for solving hard problems by flipping them on their head.

GC pro move:
Next time you’re advising on a go/no-go decision, ask:
“What would the future email look like if this blows up?”
It’ll change the conversation fast.

+ 1 AI Tool — UPDF AI

Chat with any PDF. Summarize, translate, interrogate, convert to mind maps — all in one interface.

Switch between GPT-4o and DeepSeek R1 depending on the job.

Use it to:

• Digest that 95-page SPA before lunch

• Extract the core risk items from diligence packs

• Summarize opposing counsel’s 12-page monologue into 3 bullets

+ 1 Quote to Reflect

"The greatest mistake you can make in life is to be continually fearing that you will make one."
— Elbert Hubbard

PS. Great decisions start with great talent.

Ambar is your unfair advantage when you need brainy legal advice for niche, high-stakes or urgent work. Think:

• One-off projects

• Peaks of work

• Overcoming attrition

• Secret weapon-style specialists

We’re not a marketplace. We’re a curated arsenal.

Reply if you want to see how elite legal talent can sharpen your decision edge.

Stay cool,

Rosa & Manuel