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win-loss-program

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Build a standing win-loss program that finds out why deals were actually won or lost. Use when CRM loss reasons are useless, competitive losses go unexplained, or positioning and product decisions are being made from rep-reported fields. Runs three evidence lanes: mining transcripts and threads of decided deals, interviewing the buyers themselves after the decision when there is no deal left to protect, and group customer arena sessions where the cross-functional team listens to customers walk their journey. Produces a loss-cause library, competitive findings, and themes that feed positioning, enablement, and qualification. Rule: rep-reported loss reasons are opinions; buyer-reported ones are evidence. Trigger phrases: win-loss, why did we lose, loss reasons, buyer interview, post-mortem this deal, what is killing our deals.

skills/rutger-katz/win-loss-program/SKILL.md

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# Win-Loss Program: The Truth Source for Everything Downstream

Average B2B win rates sit around 19-21% (Ebsta x Pavilion GTM Benchmarks, 2025 edition, still the latest full dataset). Read as an information problem: roughly four of five worked opportunities end in a decision your company usually never investigates. The loss-reason field in the CRM does not count as investigation. It is filled by the person with the strongest incentive to externalize the cause, seconds after the sting, from a dropdown that forces one cause where there were three. Loss fields cluster on "price" and "timing"; buyer interviews of the same deals routinely surface trust, absent capabilities, a stronger champion on the other side, or a decision that was rigged before the first call. Every downstream system inherits whichever version you record.

A win-loss program replaces attribution folklore with three evidence lanes, run on a standing cadence: mine every decided deal, interview a sample of buyers one on one, and periodically put a group of customers in one room with the whole go-to-market team listening.

## Lane 1: Transcript and Thread Mining (every decided deal)

The cheap lane, and with call recording in place, the one with no excuse. Within a week of any decision, mine the deal's full record: call transcripts, email threads, proposal versions, evaluation notes.

- Extract in the buyer's words: what they said about the problem, alternatives, money, timing, and internal politics. Verbatim quotes with timestamps, never paraphrases; a paraphrase is where wishful thinking re-enters.
- Reconstruct the decision timeline: when did the deal actually die or lock? It is almost never the dated loss event in the CRM; find the call where the energy changed and what preceded it.
- Contrast rep story vs record: write the rep's stated loss reason next to what the record shows. The recurring gap between the two, by rep and by cause, is itself a coaching output.
- Limits, stated honestly: mining only hears what was said TO you. The real reason often lives in the meeting you were not in. That is what Lane 2 is for.
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