Overview AI tools like Ask Jiminny can help your team evaluate sales calls and deals more consistently, efficiently, and objectively. However, the quality of the insights depends on how well the prompts are written to an extent. This guide will walk you through how to craft effective prompts for deal evaluation with an emphasis on scoring, reasoning, and actionable coaching feedback.
Why Prompt Precision Matters in Deal Evaluation
A well-crafted prompt:
Produces consistent and objective deal scores
Surfaces useful coaching insights
Reduces the time needed for manual review
Enables sales managers to make data-informed decisions
Bad prompts often result in vague, generic, or hallucinated feedback that isn’t actionable. Good prompts add context, structure, and constraints that guide the model to deliver high-quality evaluations.
Prompting Best Practices for Deal Evaluation
1. Add Context at the Start of the Prompt
Start by telling the model who it is, who the evaluation is for, and what the goal is. This aligns the output with the right tone and intent.
Example:
"You are a sales-performance analyst. Your report will be reviewed by the sales rep’s manager. Your goal is to provide an objective, actionable evaluation of how the rep performed on this call, so they can be coached effectively."
2. Encourage Reasoning Before Scoring
Ask the model to explain before it scores. This is known as "giving the model time to think," which leads to more accurate and grounded evaluations.
Example:
"For each criterion, provide a short explanation based on the transcript and then assign a score from 1 to 5. Include supporting quotes where applicable."
Benefits:
More thoughtful scoring
Easier to verify and trust the feedback
Enables coaching with evidence
3. Be Specific About Evaluation Criteria
List the exact areas to evaluate. Use a structured format like:
Opening: Did the rep establish rapport and set an agenda?
Discovery: Did they ask high-quality, open-ended questions?
Pain: Did they identify the key business challenges?
Next Steps: Did they secure clear next steps?
Prompt Tip:
"Evaluate the call on these 4 criteria. For each, provide reasoning and a score. Format your response as a table with columns: 'Criteria', 'Explanation', 'Score (1 to 5)', 'Quote if available'."
4. Use Scoring Anchors
If you want more consistency in scoring across calls, define what each score level means.
Example:
5: Excellent - fully met expectations
3: Average - partial effort or impact
1: Poor - missed opportunity or incorrect
Prompt Tip:
"Use this mapping to guide your scores."
5. Ask for Coaching Suggestions
Great prompts go beyond evaluation and ask the model to suggest how the rep can improve.
Example:
"After the evaluation, provide 2-3 coaching tips based on the rep’s performance."
This helps managers turn insights into action.
6. Avoid These Common Prompting Pitfalls
❌ Too vague: “How did this call go?”
❌ No criteria: “Score the call”
❌ No audience: “Write a review” (but for who?)
❌ No structure: Output is rambling and hard to read
Always provide:
✅ Role
✅ Goal
✅ Evaluation structure
✅ Reasoning before scoring
✅ Supporting quotes
Call Evaluation Example:
You are a sales performance analyst preparing a call evaluation report for a sales manager. Your objective is to provide an objective, structured assessment of the rep’s performance during this call to support coaching and improvement.
Please evaluate the call across the following four criteria:
Opening – Did the rep establish rapport and set a clear agenda?
Discovery – Did the rep ask high-quality questions to understand the prospect’s situation?
Pain Point Identification – Did the rep uncover specific business challenges or needs?
Next Steps – Did the rep clearly define and confirm next steps?
For each criterion, provide:
A 1–2 sentence explanation of the rep’s performance
A relevant quote or reference from the transcript to support your assessment
A score from 1 to 5, using the following rubric:
5 = Excellent – Fully met or exceeded expectations
3 = Partial – Some effort, but incomplete or unclear
1 = Poor – Missed opportunity or ineffective execution
At the end of the evaluation, include 2 clear and actionable coaching tips the rep can apply in future calls.
Deal Evaluation Example:
You are a revenue analyst reviewing a sales opportunity. Your goal is to evaluate the overall health and likelihood of closing this deal based on the information provided.
Please assess the deal across the following criteria:
Stakeholder Engagement – Are the right decision-makers involved and actively engaged?
Deal Momentum – Are there signs of progress or risk of stalling?
Champion Strength – Is there a strong internal advocate?
Urgency & Compelling Event – Is there a clear reason for the buyer to act now?
Next Steps Clarity – Are the next steps specific and confirmed?
For each, do the following:
Provide a short explanation (2–3 sentences)
Include a relevant quote or reference (e.g. from an email or call)
Assign a score from 1 to 5 using this mapping:
• 5 = Excellent, 3 = Moderate, 1 = Poor/Absent
At the end, give:
An overall deal health score (1 to 5) using this mapping
5 = Excellent – strong signals, no major risks
4 = Good – minor gaps but progressing well
3 = Moderate – some risks or missing info
2 = Weak – significant concerns or stalled
1 = Poor – little to no progress or clarity
A short paragraph summarizing the main risks and what actions the rep or manager should take next
Conclusion Writing great prompts is the foundation of useful deal evaluation with AI. With the right structure, context, and scoring strategy, you’ll get more accurate, actionable insights and better sales performance as a result.
Encourage your team to iterate, test, and share prompt templates to build consistency and quality into every evaluation. Now hit the save button on Ask Jiminny and share the mastered prompt with your team!