2 ways to get better at guessing

First way: try out guesses with small, reversible tests

Try out changes on a small scale—involving a few people for a short period of time—and in a way that’s easy to bail on.

Things tried out this way tend to be crappy or prototype-y. Good:

• Use a piece of paper instead of a fancy app.
• Make a spreadsheet instead of a report.
• Draw a table and figures on the wall instead of a spreadsheet.
• Do it manually today. Automate later.

Small: you need only enough work to figure out if your guess was any good. Don’t dump resources or spend time rushing towards dead ends.

Reversible: work this way to take the sting out of failure. Idea didn’t work? Stop and try the next one.

Test: once you can point to an initial success, gather resources and proceed with something more elaborate.

Second way: a logbook of guesses

Once you start testing your guesses, you’ll find that you make a lot of guesses, and run a lot of little tests. So keep a log. Write down:

• Your guess,
• What you thought might happen, and
• What actually happened.
• Was your test bigger or smaller than it needed to be?

Practice this and your guesses will improve over time.

Don’t take my word for it—try it in a small, reversible way, and see.