Win-Loss Analysis SKILL.md

This is the exact file agents read, including the credit header and licence notice. Save it as win-loss-analysis/SKILL.md.

---
name: win-loss-analysis
description: "Set up and run a win-loss programme: CRM analysis by segment and competitor, balanced selection of recent wins, losses and no-decisions, neutral buyer interviews, a consistent reason taxonomy, comparison of CRM and buyer reasons, patterns by segment, quarterly readouts and actions with owners across positioning, product, pricing and enablement. Use whenever someone asks for win-loss analysis, why deals are lost, loss reasons, no-decision deals, buyer interviews after a sale, improving win rates or checking whether price really lost the deal."
license: CC-BY-4.0
metadata:
  author: Afeez Adebayo
  author_url: https://afeezadebayo.com
  author_linkedin: https://www.linkedin.com/in/afeez-adebayo/
  author_x: https://x.com/za_icon
  source: https://afeezadebayo.com/skills-md/marketing/product-marketing/win-loss-analysis/
  category: marketing
  subcategory: product-marketing
  version: "1.0.0"
  created: "2026-10-10"
  updated: "2026-10-10"
---

# Win-Loss Analysis

When a deal is lost, the CRM usually says "price" or "no decision", typed by a rep at the end of a long quarter. Buyers tell a different story: the demo didn't show their use case, the competitor's champion was stronger, procurement found a security gap, or the case for change was never made. Win-loss analysis asks buyers directly why they chose, or didn't choose, you, then turns the patterns into changes in positioning, product, pricing, enablement and process.

This skill sets up and runs a win-loss programme: selecting deals, interviewing buyers (not reps), coding reasons, analysing patterns by segment and competitor, and turning findings into actions with owners.

## Operating principles
1. **Talk to buyers, not reps.** Rep-entered loss reasons are often wrong or incomplete.
2. **Include wins.** Knowing why you win is as useful as knowing why you lose.
3. **Neutral interviewers.** Buyers speak more freely to someone outside the sales team.
4. **Code consistently.** A stable reason taxonomy makes patterns visible over time.
5. **Close the loop.** Every quarter, findings must change something.

## Deal selection
| Deal type | Why include |
|---|---|
| Recent losses to competitors | Direct competitive insight |
| Recent wins | What works, to repeat |
| No-decision outcomes | Often the biggest hidden loss |
| Churned customers (early) | Where the sale promised more than the product delivered |
| Large or strategic deals | Highest value lessons |
Aim for 10 to 20 interviews per quarter, balanced between wins and losses, focused on deals closed in the last 90 days.

## Reason taxonomy (starting point)
| Category | Examples |
|---|---|
| Product fit | Missing capability, integration gap, usability |
| Value and price | Price, ROI unclear, packaging mismatch |
| Sales experience | Responsiveness, demo relevance, trust in rep |
| Competitor strength | Better relationship, perceived leader, bundling |
| Risk and trust | Security, compliance, references, company size |
| Decision process | Champion left, budget frozen, no urgency |
| Implementation | Effort, timeline, change management |

## When to use, and when not to
Use it when win rates change, when entering new segments, after pricing or packaging changes, when a competitor gains ground and as an ongoing quarterly programme.

Don't use it for general customer research about usage (`customer-research-interviews`) or for one-off competitor tracking (`competitive-intelligence`).

## Inputs to ask for, in one message
1. CRM export of closed deals for 6 to 12 months: outcome, reason, competitor, size, segment, cycle length.
2. Contacts for recent wins and losses who agreed to be contacted.
3. Existing loss reason fields and any past win-loss work.
4. Budget for incentives and an interviewer (internal neutral team or third party).
5. Stakeholders who will act on findings (product, sales, marketing, leadership).

## Workflow

### Step 1. Analyse CRM data
Win rates by segment, competitor, deal size, source and rep; distribution of recorded loss reasons.

### Step 2. Select deals
Recent, balanced between wins and losses, covering priority segments and competitors.

### Step 3. Recruit buyers
A short, respectful request from someone outside the sales team, with a clear purpose, 20 to 30 minutes and an incentive or charity donation.

### Step 4. Interview
Cover the trigger, evaluation process, alternatives, decision criteria, what tipped the decision and how each vendor performed.

### Step 5. Code reasons
Primary and secondary reasons using the taxonomy, with quotes.

### Step 6. Analyse patterns
Compare buyer reasons with CRM reasons; look at patterns by segment, competitor and deal size.

### Step 7. Share findings
A quarterly readout with themes, quotes and clips, tailored for product, sales and leadership.

### Step 8. Act and track
Actions with owners; track win rates in affected segments over the following quarters.

## Interview guide (25 minutes)
```
1. What prompted you to look for a solution? (trigger)
2. Who was involved, and how did you evaluate options?
3. Which options did you consider, including doing nothing?
4. What criteria mattered most, and why?
5. How did each vendor perform on those criteria?
6. What ultimately tipped the decision?
7. What could the losing vendors have done differently?
8. (Wins) What nearly made you choose someone else?
```

## CRM reason versus buyer reason
| CRM said | Buyers often said | Implication |
|---|---|---|
| Price | ROI wasn't clear for their use case | Better value story and proof |
| Lost to competitor | Competitor showed their exact workflow in the demo | Tailored demos |
| No decision | No compelling reason to change now | Stronger case against the status quo |
| Missing feature | Workaround existed but wasn't shown | Enablement on workarounds |

## Recruiting email (template)
```
Subject: 20 minutes on your recent decision about [category]?
Hi [name],
I lead research at [company] and I'm not part of the sales team. We're trying to learn how teams choose [category] tools, whatever they decide. Would you share your experience in a 20-minute call? We'll send [incentive or donation] as thanks, and nothing you say will be used to sell to you.
[name], [role]
```

## Metrics for the programme
| Metric | Why |
|---|---|
| Interviews completed per quarter | Programme health |
| Share of deals with buyer-verified reasons | Data quality |
| Win rate in segments with actions | Impact |
| Actions completed on time | Follow-through |

## Coding tips
- Record one primary reason and up to two secondary reasons per deal.
- Attach at least one quote to each coded reason.
- Review the taxonomy yearly, adding categories only when patterns demand it, so trends stay comparable.

## Sharing findings by audience
| Audience | Focus |
|---|---|
| Product | Capability gaps, usability, integrations |
| Sales | Demo relevance, discovery, competitor handling |
| Marketing | Messaging, proof, positioning |
| Leadership | Trends, revenue at stake, decisions needed |

## Edge cases and judgement calls
| Situation | What to do |
|---|---|
| Buyers won't talk | Short surveys, third-party interviewers, higher incentives |
| Small number of deals | Interview most of them; look for qualitative patterns |
| Sales resists | Share wins too; frame as helping reps win more |
| Product team disputes findings | Share recordings and quotes; tie to revenue at stake |
| Enterprise deals with many stakeholders | Interview two or three people per deal |

## Handoffs to related skills
- Competitor battlecards: `competitive-intelligence`
- Positioning and messaging changes: `positioning`, `messaging-framework`
- Pricing changes: `pricing-packaging`
- Sales materials and training: `sales-enablement`
- ICP refinements: `ideal-customer-profile`

## Worked example
An HR software company's CRM said most losses were on price. Fifteen buyer interviews told another story: in mid-market deals, buyers chose a competitor because its demo showed payroll integration with their provider, while the company's reps demoed generic features. Price was mentioned only when value wasn't clear. Actions included a demo library by payroll provider, a value calculator for mid-market buyers and new battlecard landmines about integration depth. Mid-market win rates rose over the next two quarters, and price-related losses fell.

## Output format
```
# Win-loss readout: <quarter>
## Deals analysed (wins, losses, no decision; segments)
## CRM vs buyer reasons
## Top themes with quotes
## Patterns by segment and competitor
## Actions, owners and expected impact
## Trends since last quarter
```

## Common mistakes
- Relying on rep-entered loss reasons.
- Interviewing only losses.
- Sales reps interviewing their own buyers.
- Inconsistent reason codes over time.
- Findings with no owners or follow-up.

## Questions to ask before you start
- Who will act on the findings, and how?
- Can a neutral person interview buyers?
- Which segments and competitors matter most this quarter?

## Self-check before you answer
- Are buyers interviewed, including wins and no-decisions?
- Are reasons coded consistently with quotes?
- Are CRM and buyer reasons compared?
- Does every finding have an action and owner?

## Further reading
- Clozd win-loss resources: https://www.clozd.com/blog
- Product Marketing Alliance on win-loss: https://www.productmarketingalliance.com/

---
Created by Afeez Adebayo, Marketing, SEO & Growth Expert
Website: https://afeezadebayo.com
LinkedIn: https://www.linkedin.com/in/afeez-adebayo/
X: https://x.com/za_icon
Source: https://afeezadebayo.com/skills-md/marketing/product-marketing/win-loss-analysis/

Licence: CC BY 4.0 (https://creativecommons.org/licenses/by/4.0/). You may copy, share and adapt this skill, including for commercial use, as long as you credit Afeez Adebayo and link to the source URL above. Keep this notice in any copy or adapted version.