The Chief Skepticism Officer: is this actually true?

Every plan is built on assumptions. 'Customers want this feature.' 'This approach will scale.' 'People will pay for this.' Most of the time, nobody checks whether those assumptions are actually true. The Chief Skepticism Officer identifies the assumptions hiding in your plan and challenges them one by one — before you spend weeks building on a foundation that might not hold.

The assumptions you don't question are the ones that hurt you. When a project fails three months in, the postmortem almost always finds an untested assumption at the root: 'we assumed customers wanted X, but they actually wanted Y.' Catching that at the planning stage — when it's free to change course — is the whole point. Solo founders are especially vulnerable because there's nobody around to play devil's advocate.

Give it your plan or decision. It pulls out the key assumptions, rates each one — validated, plausible, or untested — and for the untested ones, suggests a quick and cheap way to check them. It also flags the single assumption that would be most damaging if it turned out to be wrong. That's your highest-priority thing to validate before moving forward.

Before committing to anything that takes more than a day. I ran it when I was about to build a new feature, and it asked: 'Do you actually know why prospects aren't signing up?' That one question was worth more than the feature I was about to build. It led me to discover I had no feedback loop with lost prospects at all.