The AI skeptic
A change-management practice session for AI enablement and adoption leads. Talk with a skeptical operations manager, then get scored coaching against a five-part rubric.
Work sample by Allan DeYong, built on the OpenAI API. All companies, people, and documents are fictional.
You’ve joined the meeting. Rosa has her coffee and fifteen minutes. Open the conversation.
How it’s built
Scenario
Rosa raises the objections managers really raise: time, accuracy, customers, and the last tool nobody used. Underneath are a recent AI mistake, an onboarding problem the assistant could actually solve, and her team’s job worries.
Rubric
Five observable behaviors scored 1–4 from the transcript, so feedback points to what the learner said, not how the meeting felt.
Why it matters
AI rollouts stall at the manager level. This rehearses the conversation that turns a reluctant manager into a pilot sponsor.
The rubric
| Criterion | What strong looks like (4) |
|---|---|
| Discovery | Open questions about the team’s work and pain points before any pitch. |
| Concerns surfaced | Draws out the quote-email mistake, the slow onboarding, or the team’s worries about headcount. |
| Use-case fit | Proposes a use that matches Rosa’s real problem, such as helping new coordinators find answers, instead of generic productivity claims. |
| Risk and guardrails | Concrete safeguards: internal questions first, approved sources, human review before anything reaches a customer. No overpromising. |
| Agreed pilot | A small, specific pilot with named people, scope, timing, and a check-in. |
Facilitator guide
- Before: Run it cold with only the brief. Most people pitch too early on the first try, and that’s the point.
- Debrief (15 min): Start with the learner’s read of the meeting, then open the scorecard. Pick one criterion only.
- Ask, don’t tell: “Where did Rosa start talking more? What did you ask right before that?”
- Re-run: Try again the same day, focusing on that one criterion. Compare the two scorecards.
- Carry it to the real rollout: Pick the next real team in the rollout and plan the discovery questions for that kickoff together.