You’re overdue for real buyer interviews when several of these show up:
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Rule of thumb
When not to start yet. Too few closed deals to learn from, or the product is still thrashing week to week. Begin with the free positioning guides, then come back when you have enough recent wins and losses to interview.
RM dropdowns and sales speech are not the buyer’s account of the deal. Win/loss is one of the only times you hear the deal in the buyer’s exact words. Not the sales translation. Not a survey score.
~40%
hear the honest reason for the outcome
65%
CRM tags the wrong competitor
53%
losses came down to a fixable misstep
Sources: Anova / Crayon · Arkaro · Corporate Visions
Is
Structured conversations with real buyers about how the deal actually unfolded, in their words. Wins and losses. Recent enough that memory is still sharp.
Isn’t
Cleaning up CRM reason codes
A satisfaction or NPS-style rating survey
Competitive intelligence or battlecards on their own
Battlecards help you talk about a rival. Win/loss tells you what buyers actually did and said when they chose. The asset is verbatim buyer language, not a score.
Method exists to get buyer speech. Keep the motion simple.
Pull recent closed-won and closed-lost deals. Enough to see repeating patterns. Prune leavers and dead names.
One commitment only: book the interview. Within 30 days. Sender is not the AE. One follow-up only.
Sales briefs. Sales never joins. Short structured conversation, about 20–30 minutes. Behaviour and sequence.
Pull patterns. Workshop with the team. Actions for Product, Sales and Marketing. Light quarterly refresh.
Ready to turn buyer speech into who-buys-and-why? Win/loss into ICP and messaging, through Understand.
Buyers stay polite with the person they rejected. You want distance, not the AE “just checking in.”
Sales briefs the interviewer: context, what they think happened, who else was in the deal. Then sales steps out. Same honesty rule for who sends the outreach email.
Treat a paid incentive as operating practice, not a product line. Offer a voucher or a charity donation. In Germany, charity only: vouchers can read as a bribe.
If the team can’t create that distance, or leadership wants the evidence turned into positioning in the room, bring in someone outside the deal.
Kill the long rating-scale templates. Ask what actually happened, in sequence. Follow the answer, not the script.
Eight behaviour and sequence questions
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Highest value: it reaches pre-evaluation.
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A thin answer is itself a finding.
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The counterfactual. Usually the best question of the set.
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Where many deals die. The story has to travel.
The point of the interviews is not the report. It’s what the team does next. Synthesis, workshop, actions.
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Understand
Win/loss into who buys and why
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Message
Language that travels without you
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Sell
The sales story buyers can repeat
Vendor adjectives don’t travel. The phrases buyers used do. Keep evidence fresh with a light quarterly refresh.
Do it yourself
If someone on the team can keep their distance from the deal, and has time for fifteen or twenty conversations, the four steps above are the whole method.
Already paying for win/loss software? Keep it. It stores and charts the interviews. It will not decide who you should sell to. That is the workshop.
Enough to see repeating patterns. Exact counts vary by pipeline; don’t wait for a perfect sample before you start learning.
Same question spine. Wins: shorter, warmer, evaluation framing. Losses: independent-research framing, stronger no-pitch, compensation in the ask, more time, harder to book, richer when they land.
A dashboard stores and charts buyer evidence. A sprint turns that evidence into ICP, messaging and sales story in the room. Pick based on whether storage or decisions is the gap.
Leadership can evidence who the best customers are and why they buy, in the buyers’ words, and the team has actions that follow from those interviews, not from another opinion round.