Dr. No #65 – The Real Reason Every Deadline in Legal Is Wrong

Hey lawyer,

If you’ve ever estimated a timeline, felt confident…
…and then been off by a factor of three…

Congratulations: you’ve experienced the Planning Fallacy.
The psychological glitch that makes humans — and especially lawyers — chronically optimistic about timelines.

Let’s dissect it before it ruins your next quarter.

1. Food for Thought

What major project in your department looks “on track”…
…only because you haven’t looked honestly?

2. Book Insight – The Planning Fallacy (Kahneman & Tversky)

Your brain is terrible at predicting time.
Not because you’re dumb.
But because your brain loves best-case scenarios.

Why lawyers fall for it even harder:

• We assume “this time will be different.”

• We ignore complexity.

• We trust the wrong data (internal memory vs. external reality).

• We underestimate dependencies (IT, engineers, sales, procurement, the one stakeholder who replies every 17 days).

The famous Sydney Opera House example:
Planned: 4 years
Actual: 14 years
Budget: $7 million
Actual: $102 million

And yet we still think our AI rollout will be ready by May.

GC Applications:

• Use external benchmarks, not intuition

• Add 30–50% margin to all deadlines

• Shorten work cycles: deliver weekly, not quarterly

• Plan for slippage as the default, not the surprise

• Always ask: “What would make this fall apart?”

You are not forecasting.
You are risk-probabilising.

3. Mental Model – “Base Rates First” (Shane Parrish)

Forget: “How long do I feel this will take?”
Ask instead:
“How long has this taken in the past? How long does this usually take for other teams? Other companies? Other team heads?”

Base rates > instincts.

Instincts lie.
Base rates don’t.

4. AI Tool – Xmind

Mind maps + AI breakdowns + Gantt charts.
Perfect for turning a monstrous legal project into digestible steps (with realistic timelines instead of your optimistic fantasies).

5. Quote to Reflect

“Plans are worthless, but planning is everything.” — Dwight Eisenhower

P.S.

Privacy deadlines are the worst victims of the Planning Fallacy.
DPA rewrites, AI governance frameworks, Cybersecurity compliance roll-outs, Schrems II fixes…
All harder, slower, and messier than they look.

Ambar’s Fractional Privacy Counsel takes that pain off your plate:

• Drafting DPAs that regulators won’t laugh at

• Fixing global data transfer flows

• Building AI governance models fast

• Handling vendor compliance chaos

Book a call — and make your planning realistic again.

Speak next week,

Rosa & Manuel - Dr. No