Writing

Monday Question: Is the Decision Scheduled?

If a pilot is already running, here's the one thing worth checking today:

Is there an actual meeting on the calendar where someone decides expand, fix, or kill?

Not a vague intention to check in eventually. An actual date, with an actual person whose job it is to render a verdict.

If the answer is no, that's the whole diagnosis. Pilots without a decision date don't usually fail. They fade, quietly, past the point where anyone remembers exactly why it never got a real answer. The absence of a scheduled decision is the single strongest predictor of that outcome, stronger than the tool, the budget, or the team running it.

The fix costs nothing and takes five minutes: open the calendar, pick a date about a month out, and put the meeting on it now, before anyone knows what the answer will be. What happens on day 31 is the same question asked a different way, and the real math on what a faded pilot costs is why it's worth the five minutes.

If your pilot doesn't have this yet, this is the week to add it.


Structuring a pilot so it can't end ambiguously is usually the first conversation. Get in touch if yours needs one.


Rosemarie Withee has spent thirteen years helping operations teams get real work out of their software, first Microsoft 365, now AI. She’s written six books for Wiley and builds AI products at Portal Integrators.