Win/Loss Analysis Program
Learning why you win — and lose — from every deal.
Workflow
Step 1Deal Selection for Analysis
ObjectiveIdentify deals for win/loss interviews
InputCRM data, closed deals, deal outcomes
OutputDeal list for interview with contact information
Key activities
Identify recent wins for customer interviews, identify recent losses for customer/competitor interviews, ensure geographic/vertical balance, prioritize strategic deals
Decision points
Mix of wins/losses? Representative sample? Contact information quality?
Tools: CRM, deal trackingRoles: Sales (identification), Operations (coordination)
Success: Deal list with 40-50 deals identified quarterly
Quality gate: Deal list finalized, interview plan created
Why it matters
- Win/loss is the highest-signal research you have. Patterns here reveal what's really working in the market — and what's costing you deals.
Best practices
- Interview both won and lost deals — the losses teach more.
- Ask without leading; capture verbatim.
- Synthesize into patterns, not anecdotes.
- Feed the insight into positioning and coaching.
Common mistakes
- Only studying wins — selection bias.
- Leading interviews that confirm beliefs.
- Insight that never reaches the team.
Key questions
- What do we consistently win on, and lose on?
- What is the pattern behind the losses?
Agents that drive this
Deal RoomCompetitor Intel
Tools we use · alternates in [ ]
HubSpot[ Salesforce, Pipedrive, Attio ]Notion[ Confluence, Obsidian ]Exa[ Tavily, Apify, Brave Search ]