Playbook

Scoping fixes interview count and ratio, timing window, deal sourcing, and an effort range before outreach starts.

Pull the target list from the CRM directly, sized well above the interview target to account for low participation.

Secure executive sponsorship for the program's scope, not deal-by-deal approval, framed as pattern recognition, not rep review.

A win/loss outreach sequence runs three to four touches with a modest incentive, kept separate from the sales relationship.

A win/loss questionnaire moves through five stages, opening broad before narrowing, with separate win and loss variants.

Open by establishing neutrality, pace across the full question set, follow up on vague answers, and close with a clear next step.

Tag interview notes against a taxonomy built from the questionnaire's categories, adapted to an existing CRM's codes where useful.

A finding becomes a pattern at three to five independent mentions, weighted toward what recurs across losses over wins.

Run the readout as a live, cross-functional meeting built around synthesized findings, ending in a specific action per function.

A finding-type-to-function matrix maps each finding to the specific action Product, PMM, Sales, and CI should take.

Run a win/loss program on a semi-annual cadence by default, adjusted only for a specific market, pipeline, or competitive shift.

Track how many specific decisions a program's findings actually changed, not interview counts or report cadence.