S · S · Dossier steps: Sort evidence and Scenarios
Think through the what-ifs before you move
A detective doesn't arrest the first suspect who looks guilty. They list every suspect and rule them out one by one. It takes a few extra minutes, and it can save you months.
Start with the evidence board
Before you think about outcomes, sort what you have into three piles.
| Pile | What goes in it | Example: "Should I raise prices?" |
|---|---|---|
| Facts | Things you can show with records | Costs rose 12% this year. Two clients asked about rates last month. |
| Assumptions | Things you believe but haven't tested | "Most clients will leave if I raise prices." |
| Guesses | Hunches with no support yet | "My competitor is about to cut prices." |
Run three scenarios
For every real option, write a best case, a worst case and a most likely case. Keep each one to a sentence or two. The worst case matters most: if you can survive it, the decision is safer than it feels. If you can't, you need a plan B before you start.
Ask "and then what?"
First-order thinking stops at the immediate result. Second-order thinking keeps going. Cutting prices brings more customers. And then what? You have more work at lower margin. And then what? You need to hire sooner, and your cash gets tighter. One extra question often changes the answer.
Hold a premortem
Psychologist Gary Klein's premortem flips the usual review. Imagine it's a year from now and the decision failed badly. Write down why it failed. People find risks this way that they'd never name when asked "what could go wrong?", because the failure is treated as already true.
Keep more than one suspect
Investigators call it tunnel vision: locking onto one theory and only noticing clues that fit. Owners do the same with plans they like. For any decision, keep at least two real alternatives on the board, including "do nothing," until the evidence rules them out.
Where this fits in the Dossier
This page covers the two S steps of the Dossier Method: Sort the evidence, then run the Scenarios. Class II and Class III decisions use both. Your dossier records your shakiest assumption, three scenarios and the top premortem reason.
Go deeperCase file, step-by-step how-to, common mistakes and questions to work through
Case file: The big contract
A fictional example
Luis owns a landscaping company with twelve employees. A property management firm offers him a three-year contract to maintain 40 apartment complexes. It would increase his revenue by about 60%. His crew is excited. His first instinct is to sign tomorrow.
Instead, he put everything he knew on an evidence board.
- Facts: the contract price, the number of sites, payment terms of net 60 days, and a 30-day termination clause for either side.
- Assumptions: that he could hire eight more people by spring, that his trucks could cover the routes, and that the price covered his costs at that volume.
- Guesses: that the management firm would renew after three years.
Then he ran the scenarios. Best case: he staffs up smoothly and the contract becomes a steady base. Worst case: he hires and buys equipment, then the firm uses the 30-day clause after a few months, leaving him with payroll, debt and no revenue to cover it. Most likely: a rough first season while he learns the sites, then steady work.
"And then what?" changed his view. With net-60 payment terms, he'd pay two months of new wages before seeing the first check. That meant the cash gap alone was more than his reserve.
The premortem was blunt. "It failed because one client became 40% of our business and could leave in 30 days." Luis went back with three requests: payment in 30 days, a 90-day termination notice, and a phased start of 15 sites in year one. The firm agreed to the phased start and 45-day payment terms. He signed a smaller, survivable version of the same deal.
How to run what-ifs, step by step
- Draw three columns: facts, assumptions and guesses. Put every important piece of information in one of them. Be strict.
- Circle the assumption that would hurt most if it's wrong. Ask how you could test it in a week for little money.
- Write three scenarios in one or two sentences each, with a rough number where you can.
- Ask "and then what?" twice for the most likely scenario. Follow the effects on cash, people and time.
- Run a ten-minute premortem. Imagine it's a year from now and it failed. Write every reason you can think of, then rank the top three.
- Change the plan to handle the top reason. A smaller first step, a better contract term or a backup plan.
"Imagine it's a year from now and this project failed badly. Take five minutes and write down, on your own, every reason it might have failed. Then we'll go around the table, one reason each, until we run out."
Common mistakes and how to fix them
| Mistake | Fix |
|---|---|
| Only imagining the best case because the opportunity is exciting | Write the worst case first. It's easier before you're attached. |
| Treating the other side's promises as facts | Promises are assumptions until they're in writing. Contract terms are facts. |
| Running so many scenarios you never decide | Three scenarios and one premortem is enough for most decisions. |
| Ignoring timing: when money goes out vs. comes in | For any what-if involving money, sketch the cash month by month. See Cash Flow. |
Questions to work through
- What assumption is your business most dependent on right now? How would you know if it stopped being true?
- Think of a past decision that went badly. What would a premortem have caught?
- Which of your plans has only one "suspect," one way you think it can go?
- Where in your business do you treat a guess as a fact?
- What's the worst case you're quietly avoiding thinking about? Could you survive it?