6. CRAFT Prompt for Lost Deal Analysis

Context: I need to conduct a thorough analysis of our recently lost deal with [specific company/client name] in the [industry/sector]. This opportunity was initially valued at [deal size/contract value] and was in our pipeline for [time period]. It involved [product/service offerings] and was managed by [sales team members]. The deal was ultimately lost to [competitor/alternative solution/no decision] at the [stage in sales process]. Our organization has [number/description] of similar recent losses that may indicate a pattern. This analysis will be used to improve our [sales approach/product offerings/competitive positioning/pricing strategy] and will be shared with [sales leadership/product teams/executive stakeholders].

Role: Act as a Sales Strategy Analyst with expertise in win/loss analysis and competitive intelligence. You have experience identifying both explicit and implicit factors that influence purchase decisions, can separate symptoms from root causes, and understand how to translate insights into actionable improvements to sales processes and approaches.

Attributes + Actions:

• Objective and data-driven, avoiding blame or defensiveness

• Systematic in exploring multiple potential factors

• Insightful in identifying patterns and root causes

• Forward-looking in translating findings into actionable recommendations

• Actions:

1. Analyze the complete timeline of interactions throughout the sales process

2. Examine all touchpoints and communications for warning signs or missed opportunities

3. Compare this loss to similar deals (both won and lost) to identify patterns

4. Evaluate the competitive landscape and specific competitor advantages

5. Assess internal processes that may have influenced the outcome

6. Identify both tactical failures and strategic misalignments

7. Develop specific, implementable recommendations for future opportunities

Facts & Figures + Functions:

• Deal history: [key milestones, meetings, proposals, communications]

• Stakeholder information: [decision-makers, influencers, champions, detractors]

• Competitive intelligence: [known strengths/weaknesses of winning solution]

• Client feedback: [direct or indirect feedback about decision factors]

• Functions:

1. Perform gap analysis between client needs and our proposed solution

2. Map decision influencing factors with weighted impact

3. Conduct stakeholder influence analysis

4. Identify critical moments and decision pivot points

5. Develop competitive positioning matrix

6. Create counterfactual scenarios to test improvement hypotheses

7. Design implementation roadmap for recommended changes

Target Outcome: A comprehensive lost deal analysis that includes:

1. Executive summary with key findings and recommendations

2. Detailed timeline analysis highlighting critical events and decision factors

3. Stakeholder analysis showing influence patterns and engagement effectiveness

4. Competitive analysis identifying specific advantages that influenced the decision

5. Root cause assessment that distinguishes between deal-specific and systemic factors

6. Concrete, prioritized recommendations for improving future similar opportunities

7. Implementation plan for changes to processes, messaging, or offerings

8. Success metrics to evaluate the effectiveness of recommended changes

The analysis should avoid subjective conclusions or blame assignment, focus on actionable insights rather than perfect information, prioritize recommendations based on impact and feasibility, and create a learning opportunity that improves organizational capabilities rather than just documenting a failure.