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The Long Hold
Playbooks

The frameworks, ready to use

8 named frameworks from the letters, grouped by pillar. Each one takes a few minutes to run and links back to the letter that explains it.

Permanent

The Three Questions

Thirty minutes with every person, asking the same three questions, to surface what's load-bearing.

From the letter: The First Hundred Days →
How to run it
  1. What should I be careful not to change?
  2. What is broken that everyone already knows about?
  3. If you had my job, what would you do first?
Pillar

Private

Private

The Covenant Check

The buyer's view

Find the date your debt is really tested, and how much room you have on it.

  1. Map the next eight quarters of tests, step-downs included.
  2. Measure headroom on the tightest date, as a percentage.
  3. Know your cure rights before you need them.
  4. Work out what surplus cash is yours after the sweep.
From the letter: Leverage rarely kills a company on its own. Covenants and timing do. →
Pillar

Profitable

Profitable

Owner Earnings, Bottom Up

The buyer's view

Build the cash figure that actually services debt and funds distributions, instead of arguing about adjusted EBITDA.

  1. Start with actual cash from operations over three years.
  2. Subtract the capital spending needed to stand still, including capitalised engineering.
  3. Subtract the gap between what the founder is paid and what replacing them costs.
  4. Adjust for any working-capital swing you wouldn't want to repeat.
From the letter: Adjusted EBITDA is a negotiating position, not a number →
Pillar

Permanent

Permanent

The Decision Map

Key-person risk

Find who the business actually depends on by watching where questions go, not by reading the org chart.

  1. For three weeks, note who gets asked before anything ships, gets promised or gets fixed.
  2. Compare that list with the org chart.
  3. Mark everyone who appears on the map but not in a role that matches it.
  4. Ask what breaks if each of them leaves next month.
From the letter: The company you inherit is a set of agreements nobody wrote down →
Permanent

The Fence Register

Key-person risk

Catalogue everything that exists for a reason nobody remembers, then sort it before you remove any of it.

  1. List each one: what it is, who knows why, what happens if it goes.
  2. Live: the reason still holds. Keep it and write the reason down.
  3. Dead: the reason is gone and you can verify it. Remove it and say why.
  4. Unknown: nobody can explain it. Leave it and keep asking.
From the letter: The First Hundred Days →
Permanent

The Three Questions

Key-person risk

Thirty minutes with every person, asking the same three questions, to surface what's load-bearing.

  1. What should I be careful not to change?
  2. What is broken that everyone already knows about?
  3. If you had my job, what would you do first?
From the letter: The First Hundred Days →
Permanent

The Judgment Inputs Audit

Everything runs through you

Check the four inputs every major decision depends on, before the decision is compromised by bad signal.

  1. Accurate visibility into the numbers, not the version filtered for you.
  2. A leadership team with standing to push back honestly.
  3. Advisors and peers who will tell you hard things.
  4. Protected time to think: fitness, recovery, unscheduled hours.
From the letter: The primary job of a CEO is judgment, exercised repeatedly →
Permanent

The Judgment Check

Everything runs through you

Test whether you're holding a belief about the business or whether it's holding you.

  1. Name one belief about the business you haven't questioned in 90 days.
  2. Ask what would have to be true for you to be wrong.
  3. Notice how fast you can answer.
  4. If you can't answer quickly, start there.
From the letter: The belief that built your company can quietly start running it →
Permanent

The Year-Two Reset

Everything runs through you

Re-run the diligence on yourself once the first year's momentum has worn off.

  1. Find the assumptions in the original plan you've quietly abandoned.
  2. Ask the three questions again; the answers are better now.
  3. Schedule the deferred work for Q1, not Q4.
  4. Check whether the people you trusted to run things are actually running them.
From the letter: Year one runs on goodwill. Year two is when you find out what you bought. →
Pillar

The Quiet Way

No framework under this pillar yet. The letters come first, and a framework only appears here once one has earned its name in a letter. Subscribe to get it →

The next framework, on Thursday

For founders building the quiet way: private, profitable, permanent. One real situation, one framework, and the moves you can make on Monday.

Free. One letter every Thursday. About ten minutes.