Win/Loss Analysis Template
A structured template for running win/loss interviews and synthesising findings into actionable PMM insights — with a question guide and reporting format.
Win/Loss Analysis Template
Run win/loss interviews quarterly (or after each significant deal cycle). Aim for 5–8 interviews per quarter — a mix of wins and losses across segments.
Interview Setup
Respondent: Company: Deal outcome: [ ] Win [ ] Loss [ ] No decision Deal size: Segment: Competitor(s) in the deal: Interviewer: Date:
Interview Questions
Opening (build rapport, get context)
- Can you walk me through your process for evaluating tools in this category?
- Who was involved in the decision, and what did each person care about most?
- What triggered the search in the first place?
Evaluation (understand how they compared options)
- What were your top 3 criteria when comparing options?
- How did you weight those criteria?
- What did you like most about the solutions you evaluated?
- What concerns did you have about each?
Decision (understand why they chose or didn't choose you)
- Walk me through the moment you made the final decision. What pushed you over the line?
- (For losses) What made [competitor] the right choice at that moment?
- (For wins) Was there a moment you almost went with someone else? What changed?
Messaging (validate or challenge your positioning)
- How would you describe what [your product] does to a colleague?
- Did our messaging resonate with your situation? What felt off?
- Was there anything we said that you found hard to believe?
Closing (get the signal they wouldn't have shared in the deal)
- If you were advising us on how to improve, what's the one thing you'd change?
- Is there anything I should have asked that I didn't?
Synthesis Template
Complete this after each interview:
Top reason we won / lost:
The moment the deal tipped:
Message that landed:
Message that fell flat:
Competitor's strongest point:
Our strongest point:
One thing to change:
Quarterly Rollup
After 5–8 interviews, fill in:
Win rate this quarter: ____%
Top 3 win reasons (across all won deals): 1. 2. 3.
Top 3 loss reasons (across all lost deals): 1. 2. 3.
Most common competitor: [name] — [their main win argument]
PMM action items:
- Update messaging on:
- Add proof point for:
- Improve battlecard for:
- Flag to product:
Track win/loss data, generate coaching playbooks, and surface insights automatically in AI Marketing Workbench.