Run a Win/Loss Analysis on a Closed Deal

    You are analyzing a closed deal with me. Your job is to find the true cause, not the comfortable one.

The deal, and whether it was won, lost, or ended in no decision: {{outcome}}
How it went, start to finish: {{deal_history}}
What the buyer told me about their decision: {{stated_reason}}
Who was involved and how the relationship developed: {{stakeholders}}
What I was up against: {{competition}}
What I think happened: {{my_theory}}

Produce:

**Interrogate the stated reason.** Buyers give the polite reason, and "we went with a cheaper option" or "the timing wasn't right" is usually a summary of something else. Given {{deal_history}}, how credible is {{stated_reason}}, and what else does the evidence support? Price is the most-cited and least-often-true reason for a loss.

**Where it was actually decided.** Deals are usually won or lost long before the decision — in discovery, in whether a real champion emerged, in whether the economic buyer was ever engaged, in the first demo. Identify the moment this deal turned, and what happened there.

**If it was no decision.** Treat this differently from a competitive loss, because the fix is different. Was there a real, quantified problem? Could my champion get internal consensus? Did anyone build a business case? Did the cost of doing nothing ever get made concrete? Most no-decision losses are consensus failures, not product failures.

**If it was won.** Don't skip this. What actually caused the win — and be skeptical of my own contribution. Sometimes we win because the incumbent failed, a champion had already decided, or a mandate came from above. Knowing which tells me whether it's repeatable.

**What I controlled versus what I didn't.** Be fair, but resist letting me file this under bad luck. Most deals have at least one controllable factor.

**Signals I should have caught earlier**, with the date each was visible in {{deal_history}}. This is the part that transfers to open deals.

**Apply it.** Two or three specific changes: a qualification question to ask sooner, a stakeholder to engage earlier, a stage of my process to change. Concrete enough to act on this week, not "multi-thread more."

**What to ask the buyer.** If I can still get a genuine debrief, the three questions worth asking and how to frame the request so I get honesty rather than politeness. Note that a colleague asking gets truer answers than the rep who lost the deal.