E · R · Dossier steps: Execute and Review

Making the tough calls

Some decisions have no good option, only less bad ones. The goal is not to feel sure. The goal is a clear reason you can stand behind later. You can do hard things, and this page shows you how to do them well.

5 min readDossier step: E · R · Execute and reviewGo deeper ↓

First, ask what kind of door it is

In his 2015 letter to shareholders, Jeff Bezos split decisions into two types. One-way doors are hard or impossible to undo, so they deserve slow, careful thought. Two-way doors can be reversed if they don't work, so make them quickly and learn. Many owners treat every decision like a one-way door and stall the whole company.

Decide before you feel fully ready

Bezos also wrote that most decisions should be made with about 70% of the information you wish you had. Waiting for 90% usually means you're too slow. The what-if work is how you make 70% feel safe enough to act.

Write it down

For each big call, record the date, what you chose, why, what you expected to happen, and when you'll review it. In the Dossier Method that record is the dossier itself: E is making the call and setting tripwires, and R is grading it later on the Decision Quality Grid. Judge the reasoning with what you knew then, not only the outcome. Good decisions sometimes have bad luck.

Set tripwires when you decide

A tripwire is a signal you choose in advance that forces you to rethink. "If the new service hasn't covered its costs by month four, we shut it down." Decide the tripwire while you're calm, so you don't have to argue with your own sunk costs later.

Case files: common tough calls

Case 04-AClass III · one-way

Letting go of an employee who isn't working out

Third-person view
If a friend told you they'd coached this person three times with no change, what would you say?
What-ifs
Best: the team improves and morale lifts. Worst: you lose key knowledge and struggle to replace them. Likely: a hard month, then relief.
Before you act
Document the coaching, plan coverage for their work, and check employment rules where you operate.
Case 04-BClass II · two-way

Raising your prices

Third-person view
Would a new owner keep prices where they are after seeing your costs?
What-ifs
Best: margins improve and few clients leave. Worst: a big client walks. Likely: a few complaints, most stay.
Before you act
Test with new clients first, give existing ones notice, and know which clients you'd be fine losing.
Case 04-CClass III · one-way

Saying no to a big customer

Third-person view
If this customer were 40% of someone else's revenue, would you call that business healthy?
What-ifs
Best: you free time for better clients. Worst: cash drops before you replace them. Likely: a tight quarter.
Before you act
Count how many months of expenses you can cover without them. That number decides your timing.
Case 04-DClass II · two-way

Shutting down a service that loses money

Third-person view
Are you keeping it because it works, or because you built it and it feels like quitting?
What-ifs
Best: you focus on what's profitable. Worst: it was bringing in clients who bought other things. Likely: little change in total sales.
Before you act
Check whether customers of this service also buy your others. That's the clue most owners miss.
Go deeperCase file, step-by-step how-to, common mistakes and questions to work through

Case file: Closing the second location

A fictional example

Tom owns two print and sign shops. The original location is profitable. The second, opened three years ago across town, has lost money in 30 of its 36 months. It has three employees, one of them Tom's nephew. Every quarter Tom tells himself it just needs more time.

He finally ran the numbers properly. The second shop lost an average of $3,200 a month, and the first shop's profits had been quietly covering it. The lease came up for renewal in four months with a five-year term. That made it a one-way door: renew, and he was locked in until well past his planned retirement.

The sunk cost was loud in his head: "We've put $180,000 into that store." But that money was gone whether he stayed or not. The real question was only about the future: would the next five years at the second location be worth more than the alternatives?

He gathered evidence fast, because the lease deadline gave him about 70% of what he wished he knew. Most of the second shop's best customers would drive to the first location, since they ordered online anyway. The first shop had room for two more people.

Tom decided not to renew. He offered two of the three employees, including his nephew, jobs at the main shop, and gave the third two months' notice and a strong reference. He set a tripwire: if more than a quarter of the second shop's regular customers stopped ordering within six months, he'd reconsider a smaller satellite location. Six months later, the business was more profitable than it had been in three years.

How to make a tough call, step by step

  1. Name the door. Write "one-way" or "two-way" at the top of the page. If it's two-way, decide quickly and move on.
  2. Find the real deadline. A lease date, a cash date, a hiring date. Work backward from it.
  3. Remove sunk costs from the math. Cross out everything already spent. Only future costs and benefits count.
  4. Decide when you're at about 70% certainty. List the information you'd still like, and ask: would any of it change the decision? If not, decide.
  5. Plan how you'll tell people before you announce anything. See Pivot to Survive for the order.
  6. Write the decision log entry: date, decision, why, expected result, tripwire, review date.
Decision log entry · example

Date: March 3. Decision: don't renew the second location lease. Why: lost money in 30 of 36 months; customers can be served from the main shop. Expected result: higher total profit within six months. Tripwire: more than 25% of regular customers stop ordering. Review: September 3.

Common mistakes and how to fix them

MistakeFix
Letting money already spent keep a bad decision aliveAsk: "If I were starting fresh today, would I choose this?" If not, the past investment isn't a reason to stay.
Waiting for a sign that makes the decision feel easyHard calls rarely feel easy. Set a decision date and keep it.
Making a two-way decision slowlyReversible choices deserve speed. Try it, measure, adjust.
Letting personal relationships decide business questionsDecide on business grounds first, then use the relationship to deliver it with care.

Questions to work through

  1. What decision are you putting off because it's uncomfortable, not because you lack information?
  2. Where are past investments keeping you in something you'd never start today?
  3. Which of your current decisions are actually two-way doors you're treating as one-way?
  4. What would your decision log show about how you've decided this year?
  5. What tough call did you make that you're glad you made? What made it possible?