Dr. No #66 – Your Company Is Carrying Debt You’ve Never Heard Of (and it’s killing your team)

Hey lawyer,

Every GC worries about legal risk, financial risk, regulatory risk…
But the force most likely to cripple your team isn’t in the contracts.
It’s in the culture.

This week we dig into organizational debt — the silent killer of performance, speed, and sanity.
Adapted from Brave New Work, one of the smartest books Rosa and I have ever touched.

Let’s go.

1. Food for Thought

If your department had to start from scratch tomorrow — blank sheet, no history —
what rules, processes, approvals, templates, or meetings would you not rebuild?

That is where your organizational debt is hiding.

2. Book Insight — Brave New Work (Aaron Dignan)

What GCs need to know

Organizational debt is everything your company put in place “just to get by”…
…and never cleaned up.

Like financial debt, it compounds.
But instead of interest, it charges you complexity, slowness, frustration, and turnover.

Here are the big ideas — GC edition:

A. Knee-jerk rules create long-term stupidity

Someone screws up a contract → leadership adds a new approval layer.
A negotiation goes wrong → a new policy.
One complaint → a new mandatory check.

Do this long enough and a one-step process becomes a 20-step circus.
Suddenly Legal is blamed for being slow — but the real culprit is ten years of fear-driven bureaucracy.

GC takeaway: You're not slow. Your systems are clogged.

B. Yesterday’s rules are killing today’s performance

Most policies were created by people who no longer work there.
In contexts that no longer exist.
Solving problems nobody remembers.

Look at your org:

• The giant monthly meeting where nothing happens? Debt.

• Baseline budgets based on last year’s chaos? Debt.

• Social media policies written in 2009? Radioactive debt.

GC takeaway: If you wouldn’t create it today, it shouldn’t survive today.

C. Bureaucracy protects debt — debt creates bureaucracy

Org debt spawns new rules.
New rules spawn compliance rituals.
Compliance rituals spawn PMOs whose job is to manage the mess.

It’s a tragic love story between red tape and institutional fear.

GC takeaway: You can’t fix bureaucracy by adding more bureaucracy.

D. The only cure: Radical simplification

Ask:
“If we were starting from zero, what would we build?”
That question is a nuclear weapon.
It outs every irrelevant rule, redundant approval, and zombie process.

GC Action List:

• Kill one useless meeting per week

• Delete one outdated policy every month

• Reduce approval chains to the minimum lawful number

• Rebuild processes around clarity, not history

• Move from “prevent error” to “enable flow”

Simplification is not cosmetic.
It’s a strategic advantage.

3. Mental Model — The Chesterton Fence

Before you remove a rule, understand why it was created.
But if no one remembers why — it’s not a fence, it’s junk.
And junk kills velocity.

GC version: Don’t defend processes just because they exist.
Defend them because they’re useful now.

4. AI Booster — MailAI

Automate your email handling with 24/7 AI agents.
Never again drown in follow-ups, status requests, or “quick questions” that turn into 40-minute detours.

Perfect for GCs who need every minute of thinking time they can reclaim.

5. Quote to Reflect

“Every system is perfectly designed to get the results it gets.”
— W. Edwards Deming

If your team is slow, frustrated, overworked, or invisible —
the system is designed that way.

P.S.

When your internal processes are drowning in org debt, your legal team becomes the unofficial customer support line for every broken workflow.

Ambar fixes that in a Fractional or On-Demand format to:

• Rewrite messy approval flows

• Rebuild obsolete compliance processes

• Simplify contracting frameworks

• Create new legal templates

• Audit and delete useless procedures

• Redesign workflows to fit the business like a glove

We do the hard cleanup.
You get the strategic credit.

Ready to kill your org debt?
Book a call with Ambar

See you next week,
Dr. No