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Measurement

How to tell if an AI pilot is working

Decide what success and failure look like before the pilot starts, and measure against the initiative, not the demo.

Ben Ennis · October 2026 · 3 min read

Pilots rarely fail loudly. They drift. Usage tapers off, the champion moves on, and the renewal shows up before anyone has decided whether it worked. The way to avoid that is to make the decision rules before you start.

Before: write down three numbers

  • Baseline: where the outcome metric stands today, measured the same way you will measure it later.
  • Target: the number that would justify scaling, tied to the initiative.
  • Kill line: the result at which you stop, no matter how good the demo felt.

During: measure the work, not the tool

Track time per task, rework and error rates, and the share of eligible work actually going through the new path. Count the exceptions people handle by hand. Logins, prompts sent and satisfaction surveys are useful context, but they do not tell you whether the initiative moved.

After: make one of three calls

  1. 01

    Scale

    You hit the target and an owner is ready to run it. Budget it and roll it out.

  2. 02

    Fix

    You are close, and you know why you missed. Change one thing and run a short second round.

  3. 03

    Stop

    You crossed the kill line. Write down what you learned and move the effort to the next item on your map.

Stopping is a good outcome. It frees budget and attention for the work that will move the initiative, and it builds trust that AI spending is being managed like any other investment.

Want this mapped for your initiatives?

Book a free 30-minute fit call. Bring one executive initiative and we will sketch the path from it to the technology together.