War-game a trial extension policy before eligibility windows, approval paths, and messaging harden into how every "one more week" ask is handled.
Trial extension policies fail when reps learn the rule from a peer's private exception, when CRM cannot show who already extended, when product usage never enters the decision, and when extensions become a silent discount that never converts. A help-center paragraph is not evidence.
Freeze the package
State who may request an extension, the max length and count per account, who approves, how CRM records the change, and the success metric after two cohorts. Attach sample edge cases, entitlement tooling notes, finance views on deferred conversion, and attrition risk if denials feel arbitrary. If sales, CS, and product disagree on when access ends, reconcile before seating.
Name the decision you will make if the war game finds nothing new, and the kill criteria if extensions create more unpaid usage than converted revenue.
Seats
- Quota-carrying rep. What feels unfair when a peer gets a silent yes.
- Customer success. Renewal and onboarding load after a long unpaid window.
- Finance. Deferred conversion and the audit trail for each extension.
- Product. Usage signals that should gate another week.
- Skeptic. The claim that looks strongest and is least sourced.
Optional counsel seat if consumer trial rules or auto-renew disclosures bind the language. Same pack for every seat.
Run the loop
Feed Pingpong the policy memo and exhibits. First pass steelmans the rule. Later passes attack from the seats above. Final pass turns surviving objections into clearer caps, fairer edge cases, or a hold. Delete invented conversion lifts and dual-counted "extensions already covered in the playbook" claims.
Force a day-after narrative: what happens if a top prospect screenshots a peer's longer trial, if CRM cannot show prior extensions, or if entitlement tooling fails to cut access on the new date. If those stories are stronger than your fairness and systems plan, fix the package before sales leans on it. Separate product-led trials from sales-assisted pilots so expectations stay predictable.
Ask every seat to mark which approval steps are optional in practice. Optional written justifications that never run still appear in the plan doc. If managers skip logs under quarter pressure, finance and CS should treat that skip as a design failure. Write the mandatory steps into the package, then attack whether capacity can actually clear them.
When the policy leans on a long max window, force sales and finance seats to price the next cohort that will close under fear of unpaid forever access. Write eligibility, notice, and exception owners into the package, then ask those seats to attack the rules. Related: before you start a free trial, war-game a discount policy, war-game a renewal playbook, stress-test a billing change, and the war-game decisions hub. Process: how to run a Pingpong.