Writing

Monday Question: What Happens on Day 31?

If a pilot is starting this quarter, ask the sponsor this before it kicks off:

What happens on day 31?

Two answers are possible, and they predict completely different outcomes.

Specific: "We compare against the baseline we captured in week one, and the ops manager decides whether we expand, fix, or kill it." That's an experiment. Experiments are worth funding, including the ones that fail, because a clean negative result is a real answer delivered cheaply.

Vague: "We'll see how it's going." That's not a pilot. That's a subscription with optimism attached, and it will most likely end the way most pilots end, which is not with a failure but with a fade.

The fade is the expensive outcome, and it's the default one. Most pilots don't die loudly. They trail off, undecided, which means the organization pays the full cost in staff hours and attention and receives no verdict in exchange. Nobody can say whether it worked, so nobody can argue for the next one.

Three exits are legitimate: expand, fix, or kill. All three are wins, because all three produce information. Only drifting produces nothing.

The fix is almost insultingly simple: put the decision meeting on the calendar in week one, before anyone knows the answer. A pilot with a decision date behaves differently from day one, because everyone involved knows a specific person will ask a specific question on a specific morning.

I've run the actual math on what a faded pilot costs, and it's roughly twenty thousand dollars for a fifteen-person team once you count what the postmortem leaves out. The three questions worth asking before any of it starts are here.


The cheap time to structure a pilot is before it kicks off. Get in touch if yours starts this quarter.


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.