4 prompts to use with Gong AI to diagnose past deals

Prompting abilities are non-negotiable.

85% of Americans believe that AI prompting will be a critical job skill over the next five years.

Unfortunately, very few sellers have cracked the code.

So, in parts one and two of our AI prompting series, I shared eight tried-and-tested prompts you can use to win more deals and drive renewals and upsells.

Now, I’m exploring one of my favorite AI use cases: diagnosing past deals.

Old deals are a goldmine — but only if you can extract the right insights.

Use these four prompts with AI Ask Anything to uncover insights from your wins and losses, resurrect old deals, and better prepare for future buyer conversations.

Want access to all 13 prompts? Download the sales AI prompt library to learn how to deliver revenue outcomes throughout the customer lifecycle.

To win more deals in the future, you need to understand the past.

Dissecting successful deals gives insight into:

• Customer challenges and preferences
• Common objections
• Product opportunities
• The strength of your value proposition
• Typical stakeholders

Leaders: steal this prompt to identify the elements of a winning deal. Then, create a replicable playbook that new and seasoned reps can use to close more deals.

Successful sellers also examine lost deals to understand what went wrong.

Did they overlook key stakeholders?

Did they whiff on addressing the customer’s pain points?

Did they miss critical context?

Then, they use that intel to overcome similar roadblocks in the future.

Use this prompt to diagnose lost deals and avoid making the same mistake twice.

It’s the ultimate deal doctor.

Previously lost deals are a goldmine.

Second, third, and fourth attempt deals have the highest win rates.

It makes sense. With time:

• You may have built the missing feature that they needed
• Detractors may have moved on from the company
• You have a ton of context from previous attempts
• Champions may have gotten promoted
• The awareness issue is already solved

But don’t take my word for it.

Brian LaManna, Enterprise Account Executive at Gong, is an expert at turning lost opportunities into closed-won revenue.

“Over $1.1M of my 2023 closed-won revenue came from deals that already existed. Not new inbound, not cold outbound — just opportunities left for dead.” — Brian LaManna

Use this prompt to mine your lost deals for intel. Then, craft hyper-personalized outreach that reignites the conversation.

Successful loss analyses are based on data, not emotion.

When done well, they help you understand your missteps, make a more informed game plan, and avoid repeating past mistakes.

According to Klue, 56% of VPs and C-level executives said win-loss insights have increased win rates, and 53% reported more effective sales cycles.

So, how do you remove subjectivity and uncover more objective insights?

Use this prompt.

It’ll help you analyze your top five losses this quarter and identify areas for improvement.

AI prompting skills will soon be a job requirement for most sales roles.

But creating prompts that generate specific and actionable outputs can be challenging, even for the most seasoned reps.

These four prompts are designed to help you gather in-depth insights to better understand — and even resurrect — past deals.

As always, take these prompts and adapt them to fit the needs of your organization.

Want the nine other proven deal management prompts?

Download the sales AI prompt library.