Win Loss

Win/Loss Analysis

Turns a pile of decided deals into the two or three things that actually move your close rate — and separates them from the things sales says are killing deals. Those are rarely the same list.

Grounded in: The Mom Test — Rob Fitzpatrick, applied to deals rather than users: a stated reason is an opinion, a behavior is data. Ask what happened, in what order, and what they did instead — never "why didn't you buy?", which reliably returns "price" regardless of the truth. Paired with standard win/loss practice: always analyze wins alongside losses, or you have no control group.

The load-bearing idea: "we lost on price" is the most common close reason in every CRM on earth and is usually a proxy for value not established. Price is what a buyer says when the answer is no and they'd rather not explain.

When to use this

• Close rate has moved and nobody can say why with evidence.
• The same objection appears in every deal review and has never been checked against outcomes.
• Before a pricing change, a positioning rewrite, or a roadmap commitment justified by "sales keeps asking for it."
• Quarterly, as a standing input to positioning, pricing, and roadmap.
• When you're about to build a feature because one loud lost deal asked for it.

Before you start (gather these)

• At least 10 decided deals — closed-won and closed-lost both. Under ~10 you have anecdotes; say so rather than producing a confident chart.
• The stated close reason for each, from the CRM.
• Something behavioral per deal — how far it got, who was in the room, how long it sat, what the last activity was. This is what lets you go past the stated reason.
• The segment for each deal — size, industry, inbound vs outbound. Aggregate win/loss across mixed segments hides the answer.
• Who they went with instead — including "nothing" and "built it internally", which are competitors and are systematically under-recorded.

If two or more are missing, ask 2-4 clarifying questions before analyzing. The one that matters: "do we have the wins too, or only the losses?" A loss-only analysis cannot tell you what's different about losing. If the context is already in workspace/, open with an Assumptions block instead.

Process

Delegate to the researcher subagent. Send the deal notes to researcher — wins and losses in separate invocations, so neither read is anchored by the other. Ask it to tag every item stated or behavioural; the whole analysis turns on keeping those apart. If subagents aren't available on this host, run the step yourself and say so — the output is still useful, just less independent.

1. Segment before you count. Split by deal size, source, and competitor faced. A 22% overall close rate that's 40% inbound and 9% outbound is two different businesses with one misleading number.
2. Separate stated reasons from causes. Tabulate the CRM close reasons, then set them aside. They are the starting hypothesis, not the finding. Note the share that say "price" — you will come back to it.
3. Find where deals die, not why. Map each deal to the last stage it reached. Losses cluster at a stage, and the stage tells you more than the reason field: dying at first demo is a positioning problem, dying at security review is a product problem, dying after a verbal yes is a champion problem.
4. Compare wins to losses on the same variables. For each candidate cause, check the win side. If 60% of losses had no economic buyer in the room but so did 55% of wins, it isn't the cause. This step is the whole analysis — everything before it is description.
5. Test the price claim explicitly. Compare discount depth on wins vs losses, and check whether "price" losses clustered in a segment where you're genuinely mispriced or spread evenly (which means it's a value problem wearing a price costume).
6. Rank by frequency × addressability. A cause in 40% of losses that you cannot change is context. A cause in 15% that you can fix this quarter is a roadmap item. Say which is which.
7. Write findings as claims with a confidence level and a sample size. Every finding gets n= attached. Then name the two or three actions, each owned, each with the metric that would show it worked.

Output template

# Win/Loss — [period]

**TL;DR**
- [Finding 1 — the cause, the segment, and the size of the effect] *(n=[x])*
- [Finding 2] *(n=[x])*
- [The thing everyone believed that the data does not support]

**Sample:** [n] decided deals ([w] won / [l] lost), [date range]. **Confidence:** [high/medium/low] — [why].

## Where deals die
| Stage | Wins reaching | Losses dying here | Read |
|---|---|---|---|
| [stage] | [n] | [n] | [what dying here means] |

## Stated reasons vs. what the data shows
| Stated reason | Share of losses | Holds up? | What's actually going on |
|---|---|---|---|
| Price | [x]% | [yes/no/partly] | [evidence from the win side] |

## Wins vs. losses on the same variables
| Variable | Wins | Losses | Difference real? |
|---|---|---|---|
| [economic buyer engaged] | [x]% | [y]% | [yes — n=, or no] |

## Findings
### 1. [Finding stated as a claim]
- **Evidence:** [the comparison, with numbers and n]
- **Segment:** [where it's true — and where it isn't]
- **Addressable?** [yes/no, by whom, roughly how long]
- **Confidence:** [high/medium/low] — [what would raise it]

## What we believed that isn't supported
- **[The belief]** — [what the data actually shows]. [Why the belief persisted.]

## Actions
| # | Action | Owner | Metric that proves it worked | By |
|---|---|---|---|---|

## Limits of this analysis
- [Sample size, self-selection, missing segment, CRM data quality — stated plainly.]
- **Not asked:** [the question this data can't answer, and how you'd get it — usually buyer interviews.]

Avoid (anti-patterns)

• Analyzing losses without wins. Without a control you can only describe losers, never explain losing. This is the single most common way win/loss goes wrong.
• Treating CRM close reasons as causes. They're picked from a dropdown by someone moving on to the next deal.
• Accepting "price" at face value. Check discount depth on both sides before you believe it. For example, if losses averaged a 12% discount request and wins averaged 14%, price was not the deciding variable.
• Aggregating across segments. Enterprise and self-serve lose for unrelated reasons; averaged together they produce a finding that's true of neither.
• Sample sizes under ~10 presented as trends. Report the number, state that it's directional, and resist the chart.
• Forgetting "no decision" as a competitor. Deals lost to inertia are usually the largest single bucket and the most fixable.
• Ending with findings and no owner. A win/loss with no action is a document, not an analysis.

Tips

• 💡 The most useful column is "last stage reached." It requires no interviews, exists already in your CRM, and tells you more than the reason field ever will.
• If a finding survives only in one segment, that's not a weakness — that's the precision you were looking for. Say where it holds.
• Feed confirmed findings straight into positioning (if you're losing at first demo), pricing (if discount depth differs), or roadmap (if a capability gap repeats across segments).
• Re-run it every quarter with the same method. The trend across quarters is worth more than any single run's finding.