Audience
Ops / buyers evaluating AI seats and trials
Trials start with curiosity and end with “we’ll decide next month.” Next month the card renews, three people barely logged in, and finance asks why another AI line appeared. Fix that with a written kill schedule before anyone clicks Start trial.
Day 1 — set the trap while motivation is high. Name one owner (not “the team”). Write one sentence job: “This seat exists to ship X weekly.” List the artifact that counts as proof (merged PR, client brief, campaign asset set, support macro — not a playground screenshot). Cap the spend: month-to-month only; no annual prepay during trial. Note the competing seat you already pay for (ChatGPT, Copilot, Canva, etc.) so compare is forced later. Put Day 7 and Day 30 on the calendar with the same attendees as a 15-minute decision, not a workshop.
Day 7 — kill by default unless proof exists. Ask only: did at least one real work artifact ship using the tool? If zero shipped work, or nobody can name the owner, cancel the same day. Curiosity without a job is a hobby invoice waiting to happen. If something shipped, record three bullets: what the tool uniquely did, what still needed a human, and whether the competing seat could have done it in roughly the same time. Soft signals that still mean kill: “we like it” with no artifact; usage that is chat tourism; one champion and zero teammates. Stretch past Day 7 only when the artifact is real and the named job still matches.
Day 30 — keep only with a recurring job and a clear winner. By now you need evidence across multiple weeks, not a single demo high. Require a named recurring job (“long-doc rewrite every sprint,” “IDE agent on multi-file refactors,” “kickoff stills for launch week”) and a written compare against the tool you already pay for. If it only replaces something free or unused, kill it. If two seats fight for the same job, keep the clearer winner and cut the other within the meeting — do not “run both another month.” Prefer meters over vibes: usage that maps to shipped artifacts beats raw token graphs.
Money and risk checkpoints: annual plans sold during trial weeks amplify regret — stay month-to-month until three consecutive weeks of real usage show in the meter. Document the kill reason in one line in your stack doc so the next buyer does not re-trial the same tool six months later. Watch for shadow upgrades (Plus → Pro, Standard → Premium) sold as “temporary” during the trial window; treat any tier jump as a new decision with its own Day 7.
Checklist you can paste into the trial kickoff note: 1) Owner + one-sentence job + proof artifact (Day 1) 2) Competing seat named (Day 1) 3) Day 7 meeting held; ship-or-cancel recorded (Day 7) 4) Day 30 recurring job + compare vs incumbent (Day 30) 5) Kill reason or keep rationale written in one line (same day as decision)
Skip this tip if procurement already forces a scored POC with exit criteria, or if the seat is mandated by a client contract. Do not skip if your stack grew by “someone shared a magic link” or “we’ll know after we try it.”
Last verified: 27 Sep 2026 — pair with the one-seat bottleneck tip before you open a second checkout.