# Win/Loss Analysis

## Purpose
Systematically understand why you won or lost specific deals to improve product, positioning, sales process, and competitive strategy.

## When to Use
- After closing (or losing) a deal
- Improving sales conversion rates
- Refining product positioning and messaging
- Understanding competitive dynamics
- Identifying product gaps or opportunities

## Process

### 1. Capture Every Outcome

Track all deals that reach decision stage:

**Won deals:** Understand what made you the choice
**Lost deals:** Understand why they chose differently
**No decision:** Understand what prevented action

### 2. Conduct Win/Loss Interviews

**Timing:** Within 2 weeks of decision (memories fade)

**Format:** 15-30 minute call with the decision-maker

**Approach:**
- Thank them for their time
- Explain you're trying to improve
- Ask open-ended questions
- Listen more than talk
- Don't defend or sell

### 3. Win Analysis Questions

**The Decision:**
- "What ultimately made you decide to go with us?"
- "What was the deciding factor?"
- "Was there a moment when you knew you'd choose us?"

**The Alternatives:**
- "Who else did you seriously consider?"
- "How did we compare to [competitor]?"
- "What did they have that we didn't?"

**The Process:**
- "How did you make this decision?"
- "Who else was involved in deciding?"
- "What almost stopped you from choosing us?"

**The Value:**
- "What do you expect to get from working with us?"
- "What problem are you most hoping we solve?"
- "How will you measure if this was a good decision?"

**The Improvement:**
- "What would you change about our sales process?"
- "Was anything confusing or frustrating?"
- "What should we do differently next time?"

### 4. Loss Analysis Questions

**The Decision:**
- "What made you decide not to go with us?"
- "Was there a specific moment when you knew?"
- "What would have changed your mind?"

**The Winner:**
- "Who did you choose instead?" (or "Did you choose anyone?")
- "What did they have that we didn't?"
- "What was their key advantage?"

**The Objections:**
- "What concerns did you have about us?"
- "Was there anything we said or did that raised red flags?"
- "What questions did we not answer well?"

**The Fit:**
- "In hindsight, were we ever a real contender?"
- "What would make us the right fit for someone like you?"
- "Would you reconsider in the future? Under what circumstances?"

**The Process:**
- "How did our sales process compare to others?"
- "Did we provide what you needed to make a decision?"
- "What should we do differently?"

### 5. No-Decision Analysis Questions

**The Stall:**
- "What prevented you from making a decision?"
- "Is this still a priority? Why or why not?"
- "What would need to change for you to revisit this?"

**The Urgency:**
- "What was the original timeline you had in mind?"
- "What happened to push it back?"
- "Is there a trigger that would restart this?"

**The Internal:**
- "Was there internal disagreement about this decision?"
- "What other priorities are competing for attention?"
- "Who would need to be convinced to move forward?"

### 6. Analyze Patterns

After collecting 10+ win/loss interviews, look for patterns:

**Win Patterns:**
- What do winning deals have in common?
- What features/benefits are mentioned most?
- What use cases resonate?
- What personas convert best?

**Loss Patterns:**
- What objections repeat across losses?
- Which competitors are beating you? Why?
- What features/gaps are mentioned?
- What personas don't convert?

**Create a matrix:**

| Pattern | Wins | Losses | Action |
|---------|------|--------|--------|
| Price objection | 2/10 | 7/15 | Review pricing strategy |
| Integration need | 8/10 | 3/15 | Lead with integrations |
| Enterprise features | 1/10 | 8/15 | Consider roadmap priority |
| Fast implementation | 9/10 | 2/15 | Emphasize speed in messaging |

### 7. Take Action

**Product Actions:**
- Feature gaps mentioned in multiple losses
- Features praised in wins (double down)
- Integration requests

**Positioning Actions:**
- Messaging that resonates (emphasize more)
- Messaging that confuses (clarify or remove)
- Competitive positioning adjustments

**Sales Process Actions:**
- Questions that aren't being answered
- Objections not being handled
- Proof points that would help

**Qualification Actions:**
- Personas that don't convert (qualify out earlier)
- Red flags that predict loss (address or disqualify)
- Buying signals that predict win (prioritize)

### 8. Track Over Time

Monitor win/loss trends:
- Win rate by segment
- Win rate by competitor
- Most common loss reasons
- Most common win reasons

**Quarterly review:**
- Is win rate improving?
- Are the same objections repeating?
- Have product changes affected wins?

### 9. Synthesis

After conducting win/loss analysis:
- What are the top 3 reasons we win?
- What are the top 3 reasons we lose?
- What would improve our win rate most?
- Which losses were we never going to win? (bad fit)
- Which losses could we have won? (execution gap)

## Example

**Product**: B2B HR software for mid-market companies

### Win/Loss Data (Q1: 12 Wins, 18 Losses)

**Win Interview Insights:**

| Deal | Deciding Factor | Key Quote |
|------|-----------------|-----------|
| Win 1 | Ease of implementation | "We were live in 2 weeks vs. 3 months for competitors" |
| Win 2 | Customer support | "Your team felt like partners, not vendors" |
| Win 3 | Modern UI | "Our employees would actually use this" |
| Win 4 | Price | "Best value for features we actually need" |

**Loss Interview Insights:**

| Deal | Why Lost | Key Quote |
|------|----------|-----------|
| Loss 1 | Enterprise features | "Needed SOC2 compliance, you don't have it" |
| Loss 2 | Competitor (Workday) | "Our board required a name they recognized" |
| Loss 3 | No decision | "Budget got cut; maybe next year" |
| Loss 4 | Missing integration | "We needed Greenhouse integration; deal breaker" |

### Pattern Analysis

**Why We Win:**
1. Speed of implementation (8/12 wins)
2. Modern UX/design (7/12 wins)
3. Responsive support (6/12 wins)
4. Value/price ratio (5/12 wins)

**Why We Lose:**
1. Enterprise features missing (7/18 losses)
2. Brand recognition (5/18 losses)
3. No decision/budget (4/18 losses)
4. Missing integrations (2/18 losses)

### Actions Taken

**Product:**
- Prioritize SOC2 certification (addresses 7/18 losses)
- Build Greenhouse integration (addresses 2/18)

**Positioning:**
- Lead with "live in 2 weeks" messaging
- Add customer logos to address brand concern
- Create ROI calculator for budget objections

**Sales:**
- Qualify for enterprise requirements early
- Disqualify Fortune 500 (brand concern insurmountable)
- Create "speed to value" case studies

**Qualification:**
- Add SOC2 to discovery questions
- Identify integration requirements upfront
- Assess brand sensitivity earlier

### Q2 Results (Post-Actions)

- Win rate: 45% → 52% (+7%)
- Losses to "enterprise features": 7 → 3
- Losses to "brand recognition": 5 → 5 (no change)
- Average deal cycle: 45 days → 38 days

**Insight:** Win/loss analysis identified SOC2 as a solvable blocker worth fixing (high loss frequency, within our control). Brand recognition was high frequency but not actionable (can't become Workday overnight). This focused product investment on maximum win-rate impact.
