win-loss-analysis

Analyze closed deals to extract root causes and actionable sales insights.

Updated Apr 11, 2026
One-click install
npx skills add https://github.com/Jlsiles/Craig---Skills --skill win-loss-analysis-jlsiles
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: win-loss-analysis
Source: https://github.com/Jlsiles/Craig---Skills/tree/main/sales/win-loss-analysis
Command: npx skills add https://github.com/Jlsiles/Craig---Skills --skill win-loss-analysis-jlsiles

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Analyze closed deals to extract actionable intelligence that informs sales strategy, messaging, and product direction.

Core Features & Use Cases

  • Deal-profile and timeline reconstruction: capture deal details and key moments to spotlight decision factors.
  • Buyer's journey reconstruction: map the buyer's internal and external conversations to outcomes, revealing hidden objections.
  • Root-cause analysis: separate the stated reasons from signals and generate an honest assessment of what drove the decision.
  • Win-loss interviews: guide structured interviews with buyers and internal stakeholders to surface actionable feedback.
  • Batch and trend analysis: aggregate patterns across multiple deals to identify recurring gaps in ICP, pricing, or enablement.
  • Actionable recommendations: translate insights into quick wins, process changes, and strategic shifts.

Quick Start

Ask buyers for candid feedback, organize deal data and interview notes, and generate an actionable improvement plan.

Frequently Asked Questions about win-loss-analysis

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I analyze closed deals to extract actionable sales intelligence?

Analyzing closed deals requires reconstructing deal profiles and timelines to spotlight decision factors, then performing root-cause analysis to separate stated reasons from hidden objections. This process generates actionable recommendations for sales strategy and product direction.

What is the best way to conduct win-loss interviews with buyers?

Win-loss interviews require a guided framework to ensure consistent, auditable insights. By structuring conversations with buyers and internal stakeholders, you can surface candid feedback and map the buyer's journey to reveal hidden objections that drove the decision.

Can I aggregate CRM notes and deal data to identify recurring sales gaps?

Yes, batch and trend analysis aggregates patterns across multiple opportunities by incorporating CRM notes and deal data. This identifies recurring gaps in ideal customer profile, pricing, or enablement, translating insights into quick wins and strategic shifts.

Do I need structured data capture for deal review and buyer interviews?

Structured data capture is required to ensure consistent, auditable insights during deal review. You must capture specific fields like outcome, loss category, decision-maker, and timeline alongside a guided interview framework to perform effective root-cause analysis.

How do I separate stated loss reasons from actual root causes in sales analysis?

Root-cause analysis separates stated reasons from underlying signals by reconstructing the buyer's journey and mapping internal conversations to outcomes. This generates an honest assessment of what truly drove the decision, beyond initial objections.