Retention is won in sales: the five questions I ask before quoting Staywise

Controversial sales take: I disqualify 60% of demos before quoting. Retention starts at the contract, not at onboarding. The five questions:

Who owns the cancellation decision? (If they cannot name the person, the deal will churn.) What happens the week after you buy? (No plan equals no activation.) Who failed at this before us? (Learning their scar tissue beats any feature pitch.) What does "working" look like in 90 days? (Vague success equals certain churn.) Can I talk to the person who will use it daily? (Champion-only deals die in onboarding.)

Deals that pass all five close at 3x and retain at 2x. Smaller pipeline, bigger business. Yes, I have a spreadsheet. Yes, you can see it.

Agency-to-product scar tissue here. The "who failed before us" question is genius. Our worst churn was clients burned by a previous tool who projected the trauma onto us. Naming it early changes everything.

Exactly. The previous failure is in the room whether you name it or not. Name it, learn the shape of the scar, show how this time differs. Unnamed, it becomes "all tools are like this" and you churn in month four.

Ads-for-trades view: I qualify plumbers the same way. "Who answers the phone when the ad works?" No answer, no campaign. Leads that nobody calls are the paid-ads version of shelfware.

Perfect parallel. Uncalled leads and unopened software are the same churn: bought hope, no owner. The owner question fits every industry.

Sales engineer nod: "can I talk to the daily user" is where enterprise deals are won or lost. Champion-only evaluations produce beautiful pilots that die in procurement. The user interview is the real demo.