CMO · Toolkit · Intermediate · Saves 55+ hours
Win/Loss Analysis Program
A complete program for conducting win/loss analysis that produces actionable insights - not just data.
What's included
- Program Design
- Interview methodology (buyer interviews, not just sales)
- Sample selection criteria
- Interview cadence
- Third-party vs. internal considerations
- Interview Framework
- Win interview guide (15 questions)
- Loss interview guide (18 questions)
- Competitive loss deep-dive guide
- No-decision analysis guide
- Analysis Methodology
- Coding and categorization
- Pattern identification
- Quantitative aggregation
- Insight extraction
- Action Planning
- Stakeholder communication
- Recommendation development
- Feedback loop to product, sales, marketing
- Progress tracking
- Reporting Templates
- Individual interview summary
- Monthly win/loss report
- Quarterly trends analysis
- Executive summary template
Best used when
- Starting win/loss program
- Improving existing program
- Sales performance issues
- Competitive challenges
- Product roadmap input
Why this is Gold
Most win/loss programs capture data that never gets used. This program design ensures insights drive actual changes in product, sales, and marketing.
The template
The Template
PROGRAM DESIGN
Interview Mix
| Type | % of Program | Focus |
|---|---|---|
| Wins | 40% | Why we won |
| Losses | 40% | Why we lost |
| No-decision | 20% | Why they didn't buy |
Sample Selection
| Criterion | Guideline |
|---|---|
| Recency | Within 90 days of decision |
| Deal size | Mix of sizes |
| Segment | Representative |
| Competitors | Include competitive deals |
| Monthly target | 8-12 interviews |
WIN INTERVIEW GUIDE
Opening (2 min)
- Thank them for their time
- Explain purpose and confidentiality
- Confirm recording permission
Questions (25 min)
| # | Question |
|---|---|
| 1 | Walk me through how this purchase came about. |
| 2 | What problem were you trying to solve? |
| 3 | How did you first hear about us? |
| 4 | Who else did you evaluate? |
| 5 | What were your top 3 decision criteria? |
| 6 | How did we compare on each criterion? |
| 7 | What was the moment you decided we were the choice? |
| 8 | What almost stopped you from buying? |
| 9 | How was your experience with our sales team? |
| 10 | What would have made the process easier? |
| 11 | How do you describe us to colleagues? |
LOSS INTERVIEW GUIDE
Questions (30 min)
| # | Question |
|---|---|
| 1 | Walk me through your evaluation process. |
| 2 | What problem were you trying to solve? |
| 3 | Who did you evaluate? |
| 4 | What were your top 3 decision criteria? |
| 5 | How did each vendor compare on those criteria? |
| 6 | What was missing from our offering? |
| 7 | How was your experience with our sales team? |
| 8 | When did you realize we weren't the choice? |
| 9 | What would have changed your decision? |
| 10 | Is there anything we could have done differently? |
| 11 | Would you consider us for future needs? |
ANALYSIS FRAMEWORK
Category Coding
| Category | Sub-Categories |
|---|---|
| Product | Features, roadmap, integration |
| Price | Cost, packaging, terms |
| Company | Size, stability, support |
| Sales | Process, responsiveness, demo |
| Competition | Specific competitor advantages |
Pattern Identification
| Pattern Type | Signal |
|---|---|
| Consistent | 3+ mentions across interviews |
| Emerging | 2 mentions, new theme |
| Anomaly | 1 mention, unusual |
ACTION PLANNING
Insight to Action Template
| Insight | Frequency | Impact | Recommended Action | Owner |
|---|---|---|---|---|
Frequently asked questions
What is the Win/Loss Analysis Program?
A complete program for conducting win/loss analysis that produces actionable insights - not just data.
Who is the Win/Loss Analysis Program for?
It is built for CMOs and their teams working on Product Marketing. The AI coach adapts it to your company, stage, and goals.
How long does the Win/Loss Analysis Program take to use?
It saves roughly 55+ hours versus building from scratch. Our AI coach can tailor the toolkit to your situation in minutes, then hand you a step-by-step plan.
Is the Win/Loss Analysis Program free?
Yes. You can read the full toolkit and start getting coached through it for free. Sign in to save your tailored version and track your next steps.
How does the AI coach help with the Win/Loss Analysis Program?
The coach teaches you the framework, asks a few questions about your business, tailors the toolkit to you, and gives you measurable next steps to execute.