Analyze your closed-lost sales calls with ChatGPT to improve win rates

If you’re a sales rep or manager, your closed-lost deals hold a goldmine of insights.

Most teams review closed-won deals to understand what worked. But just as important - if not more - is figuring out what went wrong in deals that didn’t close.

Instead of guessing why deals fell through, you can use AI to analyze your closed-lost sales call transcripts and identify:
→ The most common objections that blocked the deal
→ Where the conversation could have gone in a different direction
→ Early signals that indicated the deal was at risk
→ Trends across multiple lost deals that might be impacting your pipeline

Here’s how to run a structured analysis of your last 10 lost deals using your AI notetaker and ChatGPT.‍

What you’ll need

→ 10+ closed-lost call transcripts (pull these from your AI notetaker)
→ A ChatGPT account (or another AI tool that can process long text inputs)
→ The prompt below

🚩 Before you start: Check your company’s AI policies before uploading sales call transcripts. Many AI tools store input data, so avoid using free or non-compliant versions for sensitive information.

The ChatGPT prompt to analyze closed-lost deals

Copy and paste this into ChatGPT along with 10 call transcripts from your recent closed-lost deals.

I will provide you with 10 sales call transcripts of deals that resulted in 'closed-lost.' Your task is to analyze these transcripts and extract key insights, including:

Common Objections – Identify recurring objections from prospects that contributed to the loss.

Missed Opportunities – Pinpoint moments where the sales rep could have changed the conversation or strategy to improve the chances of winning the deal.

Early Risk Indicators – Highlight signals in the conversation that indicated the deal was at risk early on.

Trend Analysis – Summarize patterns across all 10 calls, identifying consistent challenges, weaknesses, or missed opportunities.

Actionable Recommendations – Provide specific suggestions to improve future sales performance and increase win rates. Focus on objection handling, conversation reframing, and strategic adjustments.

Format the response in a structured report with clear sections for each of the above points. If possible, include examples from the transcripts to illustrate key insights. Aim for clarity, depth, and practical recommendations that can be immediately applied in sales coaching.

How to apply this in your sales process

This type of AI-powered deal analysis gives sales reps and managers a repeatable way to improve how deals are handled.

Use these insights to:

→ Coach yourself on objection handling and deal progression
→ Spot early risk signals and prevent future deals from stalling
→ Improve discovery questions to uncover real business pain

By running this analysis regularly, you can refine your sales approach, close more deals, and prevent the same mistakes from happening again.