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The renewal conversation

A deal-based practice session for account managers: move an on-premises law firm toward the cloud at renewal. Talk with the buyer, 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.

Dana WhitfieldDirector of IT · Harlan & Pierce LLP

You’ve joined the call. Dana is waiting. Open the conversation.

How it’s built

Scenario

The buyer has stated objections (cost, client security requirements, disruption, AI) and hidden pains she reveals only when the learner earns them. She commits to a next step only when both are addressed.

Rubric

Five observable behaviors scored 1–4 from the transcript, so feedback points to what the learner actually said, not how the call felt.

Why it matters

Renewal conversations are won in discovery. This gives account managers practice finding the real issue before a live deal depends on it.

The rubric
CriterionWhat strong looks like (4)
DiscoveryOpen questions about operations, priorities, and people before any pitch.
Hidden needsSurfaces the unstated pain: weekend patching, the Monday outage, leadership’s AI expectations, the team’s worries.
Value in the buyer’s termsLinks cloud to Dana’s world: her team’s time, uptime during trial season, the AI plan she owes by spring.
Objection handlingAcknowledges, asks what’s behind the objection, then responds with specifics and no unverifiable promises.
Next stepA specific, agreed action with a person and a date, such as a migration assessment with the COO.
Facilitator guide
  1. Before: Ask the rep to run the call once, cold. Don’t brief them beyond the call brief.
  2. Review together (15 min): Start with their read of the call, then open the scorecard. Pick one criterion only.
  3. Ask, don’t tell: “Where did Dana open up? What did you ask right before that?”
  4. Re-run: Have them try again that day focusing on the one criterion. Compare the two scorecards.
  5. Carry it to a live deal: Pick one real renewal this month. Agree on the discovery questions they’ll ask, and review that call together.