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.

3 min readDossier step: E · R · Execute and review

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.