win-loss-analysis

name: win-loss-analysis description: > Systematic post-deal analysis skill for B2B sales teams — covers win/loss interview design, deal data extraction from CRM exports, competitive intelligence synthesis, pattern recognition across deal outcomes, and executive reporting. Use this skill whenever a user mentions win/loss analysis, deal post-mortems, lost deal reviews, why we lost, why we won, competitive win rates, deal retrospectives, buyer feedback analysis, post-decision interviews, competitive intelligence from deals, loss reason analysis, win rate improvement, deal outcome patterns, or sales forensics. Also trigger when the user has CRM export data (Salesforce, HubSpot, Pipedrive, Close) with deal outcomes and wants to understand patterns, or when they have interview transcripts/notes from buyers who chose a competitor. Even if they just say "figure out why we're losing deals" or "what's our competition doing better" — this is the skill for that.

Win/Loss Analysis Skill

Transform raw deal data and buyer feedback into actionable competitive intelligence. This skill covers the full win/loss lifecycle — from designing interview programs and extracting CRM data through pattern analysis, competitive positioning insights, and executive-ready reporting.

Quick Start

Before beginning any analysis, check for existing context:

Look for: .agents/product-marketing-context.md

If it exists, load it for product positioning, competitive landscape, and ICP details. If not, ask the user for their product/service, key competitors, and typical deal size before proceeding.

The Three Pillars of Win/Loss Intelligence

Effective win/loss programs triangulate three data sources. Each one alone is incomplete — together they tell the real story.

1. Buyer Interviews (Primary Intelligence)

The gold standard. Direct conversations with decision-makers who evaluated your product, whether they chose you or not. This is where the genuine "why" lives — the narrative that CRM dropdowns and seller opinions can never capture.

2. Seller Debriefs (Internal Perspective)

Your sales team's account of what happened. Valuable for process insights (where did the deal stall, what objections came up, how did pricing discussions go) but inherently biased — sellers tend to externalize losses ("price was too high", "they had an existing relationship") and internalize wins.

3. CRM/Deal Data (Quantitative Foundation)

Structured data from your CRM — deal stages, timelines, competitors involved, deal size, industry, close dates, loss reasons. Provides the statistical backbone for pattern recognition across hundreds of deals.

Interview Program Design

Interview Timing

Timing matters enormously for interview quality. Buyer memory degrades predictably:

The sweet spot is 14 days. Push to interview within this window for your most important deals.

Interview Question Framework

Structure interviews in four phases. Each phase builds on the previous one, moving from context to decision specifics.

Phase 1: Context Setting (5 minutes)

Establish the business problem and buying trigger. Don't jump into competitive questions — understand why they were in-market at all.

- What business challenge prompted this evaluation?
- Who was involved in the decision? What were their roles?
- What was your timeline, and what was driving it?
- Had you used a similar product/solution before?

Phase 2: Evaluation Process (10 minutes)

Understand how they structured their evaluation and what criteria mattered most. This reveals their decision framework — often different from what your sales team assumed.

- How did you build your shortlist of vendors to evaluate?
- What were your top 3 evaluation criteria? How did you weight them?
- What did your evaluation process look like — demos, trials, references?
- Were there any "must-have" requirements that eliminated vendors early?
- How did internal stakeholders influence the criteria?

Phase 3: Competitive Dynamics (15 minutes)

The heart of the interview. This is where you learn what really happened in the competitive evaluation.

- Which vendors made your final shortlist?
- How did you perceive each vendor's strengths and weaknesses?
- Were there specific capabilities where one vendor clearly stood out?
- How did pricing compare across vendors? Was pricing a deciding factor?
- Did any vendor do something during the process that significantly helped or hurt their chances?
- Were there any "moments of truth" — specific interactions or demos that shifted your thinking?

Phase 4: Decision & Reflection (10 minutes)

Understand the final decision and capture hindsight that often reveals deeper truths.

- Walk me through the final decision. What tipped the scales?
- Was it a unanimous decision, or were there internal disagreements?
- Looking back, is there anything [your company] could have done differently?
- How confident are you in the decision today?
- What would you tell other buyers evaluating similar solutions?

Interview Best Practices

• Use a neutral third party when possible. Buyers are more candid with someone who isn't their sales rep. Even an internal PM or product marketer who wasn't on the deal works better than the AE.
• Record with permission. Transcripts are gold for pattern analysis later. Always ask, and note that it's for internal improvement purposes only.
• Follow the energy. If the buyer gets animated about a topic, go deep there. The most valuable insights often come from unscripted tangents.
• Resist the urge to sell. This is a listening exercise. The moment you start defending or explaining, the buyer stops being honest.
• Ask "What else?" After every major answer. The first response is usually the socially acceptable one. The real insight comes in what they add when you stay quiet.

CRM Data Analysis

Required Data Fields

For meaningful quantitative analysis, you need at minimum:

Analysis Dimensions

Run the scripts/win_loss_analyzer.py script against your CRM export to generate analysis across these dimensions:

Win Rate Analysis

• Overall win rate and trend over time
• Win rate by competitor (which competitors do you beat most/least often?)
• Win rate by segment (industry, company size, deal size)
• Win rate by sales rep (performance distribution)
• Win rate by lead source (which channels produce the most winnable deals?)

Loss Pattern Analysis

• Loss reason distribution (what's the #1 reason you lose?)
• Loss reason by competitor (do you lose to different competitors for different reasons?)
• Loss reason trends over time (are new patterns emerging?)
• Stage-of-loss analysis (where in the funnel do deals die?)
• Deals lost at proposal stage vs. earlier (pricing issues vs. qualification issues)

Competitive Landscape

• Competitor encounter frequency (who do you see most often?)
• Head-to-head win rates per competitor
• Competitor strengths/weaknesses (synthesized from interviews + data)
• Competitive displacement patterns (who's taking your existing customers?)
• New entrant detection (competitors appearing for the first time)

Temporal Patterns

• Seasonal win rate variations
• Sales cycle length by outcome (do wins close faster or slower than losses?)
• Time-to-decision by segment
• Trend analysis: is your win rate improving or declining?

Synthesis Framework

The real value isn't in any single interview or data point — it's in the patterns that emerge across many deals. Use this three-level synthesis framework:

Level 1: Deal Narrative

For each individual deal, create a structured summary:

Deal: [Company Name] — [Won/Lost]
Value: $[amount] | Industry: [vertical] | Size: [employees]
Competitors: [list]
Decision Trigger: [what prompted the evaluation]
Key Criteria: [top 3 buyer priorities]
Competitive Dynamics: [how you compared on their criteria]
Decisive Factor: [what ultimately tipped the decision]
Primary Loss/Win Reason: [one-liner]
Actionable Insight: [what could be done differently]

Level 2: Thematic Patterns

After 10+ deal narratives, patterns emerge. Look for:

• Recurring loss themes: Are you consistently losing on the same capability, pricing model, or competitor tactic?
• Winning formula: What do your wins have in common? Specific segments, deal sizes, competitive scenarios?
• Perception gaps: Where does buyer perception differ from your positioning? ("We thought we were competing on innovation, but buyers see us as the safe choice.")
• Process breakdowns: Are there systematic failures in your sales process that correlate with losses?

Level 3: Strategic Implications

Roll thematic patterns up into actionable strategic recommendations:

• Product: Feature gaps that cost you deals, capabilities that win deals
• Pricing: Competitive pricing dynamics, packaging issues, discounting patterns
• Sales Process: Where deals stall, what messaging works, training needs
• Marketing: Positioning adjustments, competitive battle card updates, content gaps
• Go-to-Market: Segments to double down on, segments to deprioritize

Reporting Templates

Executive Summary Report

The executive audience needs: key numbers, competitive position, top 3 actions. Use the script scripts/win_loss_report_generator.py to produce the report structure from analyzed data.

# Win/Loss Analysis Report — [Period]

## Key Metrics
- Overall Win Rate: [X%] (↑/↓ [Y%] vs prior period)
- Deals Analyzed: [N] won, [M] lost
- Top Competitor: [Name] — encountered in [Z%] of deals

## Top 3 Findings
1. [Finding with data point and implication]
2. [Finding with data point and implication]
3. [Finding with data point and implication]

## Competitive Position
[2×2 matrix or ranked list showing competitive standing]

## Recommended Actions
1. [Action] — Owner: [team] — Impact: [expected improvement]
2. [Action] — Owner: [team] — Impact: [expected improvement]
3. [Action] — Owner: [team] — Impact: [expected improvement]

## Appendix
[Detailed data tables, interview summaries, methodology notes]

Competitive Battle Card Updates

Win/loss insights feed directly into competitive battle cards. For each competitor analyzed, produce:

# [Competitor Name] — Battle Card Update

## Where We Win Against Them
- [Strength 1 — with supporting deal evidence]
- [Strength 2]

## Where We Lose to Them
- [Weakness 1 — with supporting deal evidence]
- [Weakness 2]

## Their Typical Positioning
[How they pitch against you, based on buyer feedback]

## Effective Counter-Positioning
[What messaging works when you encounter them, based on wins]

## Traps to Avoid
[Messaging or tactics that backfired in lost deals]

## Key Differentiators to Emphasize
[Capabilities that buyers valued where you outperformed]

Scripts & References

The scripts/ directory contains automation tools:

• scripts/win_loss_analyzer.py — Ingests CRM export CSV/XLSX and produces quantitative analysis (win rates, loss patterns, competitive landscape, trends)
• scripts/win_loss_report_generator.py — Generates executive summary report structure from analyzed data
• scripts/interview_synthesizer.py — Processes interview notes/transcripts and extracts structured deal narratives + thematic patterns

The references/ directory contains lookup data:

• references/interview-guide.md — Complete interview question bank organized by phase, with probing follow-ups and common buyer deflections
• references/loss-reason-taxonomy.md — Standardized loss reason categories with definitions and CRM coding guidance
• references/report-templates.md — Full report templates for executive summary, competitive battle cards, and product feedback reports
• references/benchmark-data.md — Industry benchmark win rates by segment, deal size, and competitive scenario

Related Skills

• sales-call-analysis: Analyze recorded sales calls for talk patterns, objection handling, and coaching insights
• analytics-reporting: Build dashboards and visualizations from the quantitative output
• content-strategy: Use competitive insights to inform content and positioning