Dr. No #74 – 7 paradoxes that explain many things in your life and teams

Hey lawyer,

I’ve been thinking about this all week.

What if the reason your team reacts in strange, frustrating, sometimes irrational ways…
is not because they’re wrong —
but because they’re human?

Here’s the uncomfortable question.

(i) Uncomfortable question

What if the behaviour driving you mad in your team
is actually a perfectly logical response to the way the system is set up?

(ii) 7 paradoxes that explain many things in your life and teams

Over the years, I’ve noticed something odd.
The best GCs don’t just know the law.
They understand paradoxes — those situations where common sense lies to you.

Here are my seven favourites. If you recognise your team in them, congratulations: you’re paying attention.

1. The Paradox of Choice

Logic says more options mean more freedom.
Psychology says more options mean anxiety and paralysis.

Give your team five acceptable ways to do something, and they’ll debate forever.
Give them two, and they’ll decide.

Better GC move:
Constrain options on purpose. Fewer choices, faster decisions, less regret.

2. The Icarus Paradox

The same wings that made Icarus great also destroyed him.

Your best lawyers fall into this trap:

• The perfectionist becomes slow.

• The risk-spotter becomes a blocker.

• The control freak kills initiative.

Better GC move:
Treat strengths like medicine. The right dose helps. Too much poisons.

3. Solomon’s Paradox

King Solomon gave brilliant advice to others… and ruined his own life.

We are much wiser advising others than advising ourselves. Distance creates clarity.

This is why Rosa and I are co-CEOs.
We borrow each other’s distance.

Better GC move:
Before deciding, ask:
“What would I advise another GC in my position?”
Then do that.

4. The Region-Beta Paradox

People recover faster from terrible situations than from mediocre ones.

A catastrophic failure triggers action.
A tolerable mess is endured forever.

Better GC move:
Don’t tolerate “almost broken” processes.
Either fix them or break them cleanly and rebuild.

5. The Abilene Paradox

A group agrees to do something that nobody actually wants.

Why?
Because everyone assumes everyone else wants it.

Congratulations, you’ve just scheduled another useless monthly meeting.

Better GC move:
Say what others won’t:
“Does anyone actually think this makes sense?”

You’ll be surprised how relieved people feel.

6. The Persuasion Paradox

The most persuasive people don’t argue.

Arguments trigger defensiveness.
Listening triggers openness.

If you push, people push back.
If you listen, they lean in.

Better GC move:
Replace “Here’s why you’re wrong” with
“Help me understand how you see this.”

Influence follows curiosity.

7. The Failure Paradox

If you want more success, you need more failure.

Every expert has failed more times than the beginner has even tried.

Better GC move:
Create safe spaces for small, early failures — before the expensive ones arrive.

So how does this make you a better GC?

You stop reacting to behaviour.
You start redesigning the system that produces it.

That’s leadership.

(iii) Mental model — Inversion (Charlie Munger)

Instead of asking,
“How do I make my team better?”

Ask,
“What guarantees my team becomes slow, defensive, and disengaged?”

Then stop doing those things.

Avoiding stupidity beats chasing brilliance.

If you have been a Dr No reader for a while, you know Rosa and I love inversion thinking.

(iv) AI Booster — Liminary

Liminary lets you save and recall anything in one click using AI.

Why this matters for senior lawyers:

• Judgment compounds only if you remember past lessons.

• Meetings blur. Decisions fade. Context gets lost.

Concrete use case:
After a tough negotiation or internal conflict, save the key insight.
Six months later, recall it instantly when the same pattern appears again.

That’s how experience turns into wisdom.

(v) One quote

That’s what paradox literacy gives you.

And sometimes, the smartest move isn’t thinking harder —
it’s bringing in senior judgment from the outside.

At Ambar, we help GCs do exactly that.

Fractional senior counsel for retail and consumer legal needs, when it actually matters:

• FMCG and consumer contracts

• Labelling and packaging complexity

• Marketing, publicity and distribution niche regulations

• Notices, sanctions and claims from the administration

• Retail and consumer disputes that drain internal teams

No fixed cost.
No learning curve.
Just people who’ve already been there.

This is exactly when clients call us.

Until next week,
Dr. No