Most of the bad decisions I've made felt obvious at the time. That's what makes them dangerous. In the room, with a good salesperson across the table and a number that looks right, everything feels obvious.
So I made a rule. Anything that commits serious money, or changes who I work with, gets one page before I say yes. Typed or handwritten, it doesn't matter. It just has to exist.
What goes on the page
The same four headings, every time.
- What I'm deciding. One sentence. If it won't fit in one sentence, I'm deciding two things and I need two pages.
- Why now. What happens if I wait a month? Surprisingly often the answer is nothing, and the urgency belonged to someone else.
- What would have to be true. The assumptions, written as plain sentences I could be wrong about. Revenue holds at this level. The partner does what they say. The market doesn't turn.
- How I'll know I was wrong. A date and a number. If it hasn't happened by then, I stop or change course. The psychologist Gary Klein built a whole method around this idea, the premortem, where a team imagines the project has already failed and works out why.1
Why a page beats a conversation
Talking a decision through with people I trust is useful, but conversation flatters. People nod. I fill the gaps with confidence. A weak assumption slides past because nobody wants to be the one who slows things down.
Paper doesn't nod. A sentence like "the client will renew" looks thin when it sits alone on a line with nothing underneath it.
The page also has to survive a night. I write it in the evening and read it again in the morning. More often than I'd like to admit, the morning version of me crosses something out.
What it costs
A day, usually. Once in a while, a deal, when the other side wanted an answer in the room. I've made peace with that.
The deals that can't wait a day are rarely the ones I regret missing.
What it gives back
The obvious benefit is fewer mistakes. The less obvious one is that the pages pile up. I keep them in one folder and read back through them every few months. Patterns show up that I would never see from memory: the same optimism about payment terms, the same habit of underestimating how long it takes to hire well.
Daniel Kahneman spent a career showing how confidently people misjudge their own plans.2 A folder of my own old pages makes the same point, with my handwriting on it.
A few of those pages became essays on this site. Most stay private, which is the point. They were never written to convince anyone except me.
If you want to try it
Start with one decision
Pick the next decision that makes you slightly nervous and give it the four headings. Don't polish it. Nobody else is going to read it.
Sleep on it
Read it once more in the morning, before you act. You'll either make the same decision with more confidence, or you'll find the thing you were hoping nobody would ask about. Both are worth a day.
Sources
Sabir Salim Shaikh
Founder, chairman and managing director of SAVIANS Group in Pune. He writes about building and running businesses, from the decisions that worked and the ones that didn't.
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