ChatGPT Prompts for Navigating a Stalled Deal

Every salesperson faces stalled deals at some point. Prospects who were once engaged suddenly go quiet, emails go unanswered, and calls are ignored. To navigate these situations effectively, sales professionals need strategies to re-engage prospects, uncover hidden objections, and revive the sales process.

Handling stalled deals properly helps to:

• Recover potential revenue – Prevent good opportunities from slipping away.
• Optimize sales pipeline health – Identify and manage risks proactively.
• Improve sales efficiency – Save valuable time by focusing efforts where they're most effective.
• Maintain strong prospect relationships – Preserve rapport and trust even when progress slows.
• Gain insights for future deals – Understand why stalls happen and how to avoid them in future engagements.

Below are detailed ChatGPT prompts, structured examples, and actionable strategies for sales reps to successfully navigate and revive stalled deals.

1. Prompt for Re-engagement Email (Gentle Check-In)

ChatGPT Prompt:

Write a polite and engaging re-engagement email to a prospect who stopped responding during the negotiation phase.

Example Email:

Subject: Checking In – How Can We Help?

Hi [Prospect Name],

Hope you're doing well! I wanted to touch base since we last discussed [your product/service] and how it could help with [key pain point]. I realize things might be busy on your end, so I wanted to ask if addressing this is still on your priority list.

If there’s been any changes or questions we haven't answered, please let me know. I'm here whenever you’re ready to reconnect!

Best,
[Your Name]

2. Prompt for Direct Inquiry Email (Clarifying Status)

ChatGPT Prompt:

Write a direct but polite email to a prospect asking if they're still interested or if their priorities have changed.

Example Email:

Subject: Quick Status Update on [Deal or Project Name]

Hi [Prospect Name],

Just following up on our previous conversations about [specific product/service] for [their company].

I wanted to see if this is still something you’re looking to move forward with, or if your priorities have shifted. Either way, your clarity will help me support you better.

Let me know what you think—thanks!

Best regards,
[Your Name]

3. Prompt for Providing Additional Value (Sharing Insight)

ChatGPT Prompt:

Write a follow-up email to a prospect who went quiet, providing a valuable resource or insight relevant to their needs.

Example Email:

Subject: New Insights on [Relevant Topic] for [Company Name]

Hi [Prospect Name],

I thought you might find this [article/case study/industry report] useful—it discusses recent trends and solutions for [specific issue relevant to prospect].

Given our previous discussion about [their pain point], I think you’ll find it valuable. Let me know if you'd like to discuss any insights further!

Warm regards,
[Your Name]

4. Prompt for Identifying Unspoken Concerns (Asking Open Questions)

ChatGPT Prompt:

Create an email that gently encourages a stalled prospect to share any unspoken concerns or reservations.

Example Email:

Subject: Anything We Can Address?

Hi [Prospect Name],

I understand decisions like this can be complex and involve many considerations. If there are any remaining questions, concerns, or hesitations on your mind, I’m more than happy to discuss and find solutions together.

Please don’t hesitate to share what’s on your mind—your comfort is my priority.

Looking forward to hearing from you.

Best,
[Your Name]

5. Prompt for Offering an Incentive or Urgency (Limited-Time Offer)

ChatGPT Prompt:

Write a follow-up email offering a limited-time incentive to a prospect who has stopped responding.

Example Email:

Subject: Exclusive Offer for [Company Name]—Ends Soon

Hi [Prospect Name],

I wanted to mention we’re currently offering [specific incentive, e.g., a discount, additional service, free onboarding] if you’re able to finalize things by [specific date].

I thought this might be timely given our recent discussions. Would you like more details or assistance moving forward?

Warm regards,
[Your Name]

6. Prompt for Multi-Channel Re-Engagement (LinkedIn Message)

ChatGPT Prompt:

Write a short LinkedIn message to reconnect with a prospect who has stopped responding to emails.

Example LinkedIn Message:

Hi [Prospect Name],

Hope all is well! I’ve tried reaching out via email but realize things might be busy. Thought I’d try connecting here as well. If addressing [their pain point] is still on your radar, I'd be happy to reconnect whenever you're available.

Take care,
[Your Name]

7. Prompt for Escalation Email (Involving Leadership)

ChatGPT Prompt:

Write an email introducing a senior team member to a stalled prospect, suggesting a high-level conversation to move forward.

Example Email:

Subject: Introducing [Senior Leader's Name] for Further Assistance

Hi [Prospect Name],

Given your earlier interest in [your product/service], I wanted to introduce [Senior Leader’s Name & Title] at [Your Company]. They can provide additional insights and help address any remaining concerns.

Would you be open to a brief call together to discuss this at a strategic level?

Looking forward to hearing your thoughts.

Best regards,
[Your Name]

8. Prompt for "Breakup" Email (Polite Last Attempt)

ChatGPT Prompt:

Write a respectful "breakup" email to a prospect who hasn't responded despite several attempts, leaving the door open for future re-engagement.

Example Email:

Subject: Closing the Loop – For Now

Hi [Prospect Name],

I've reached out a few times but haven't heard back. I completely understand that timing and priorities can shift, so I'll go ahead and close your file for now.

If anything changes or you want to revisit this, please reach out anytime. It’s been a pleasure connecting!

All the best,
[Your Name]

9. Prompt for Phone Call or Voicemail Script (Direct Check-In)

ChatGPT Prompt:

Write a brief script for leaving a polite voicemail for a stalled prospect to re-engage them.

Example Script:

"Hi [Prospect Name], this is [Your Name] from [Your Company]. Just wanted to quickly check in and see if addressing [specific pain point or topic] is still important to you. Whenever you have a moment, I'd appreciate a quick update. You can reach me at [Your Phone Number]. Thanks again!"

10. Prompt for Customer Success Story Follow-Up

ChatGPT Prompt:

Write a follow-up email sharing a relevant success story or testimonial to encourage a stalled prospect to reconnect.

Example Email:

Subject: How [Similar Company] Benefited from [Your Solution]

Hi [Prospect Name],

I wanted to quickly share how [Similar Company] recently overcame similar challenges using our solution. They achieved [specific measurable result] in just [timeframe], significantly improving their [key outcome].

Thought you’d find this encouraging, given your goals. If you’re interested, we can discuss how this might look for you.

Best,
[Your Name]

Final Thoughts: Key Strategies for Reviving Stalled Deals

• Stay empathetic and understanding: Be patient and respectful, never pushy.
• Provide consistent value: Share insights, resources, or offers that truly benefit prospects.
• Vary your approach: Combine emails, phone calls, LinkedIn messages, and more.
• Involve senior leadership strategically: Elevate conversations when necessary to move things forward.
• Know when to step back: Send polite "breakup" emails to leave the door open gracefully.

Use these detailed ChatGPT-powered prompts to navigate stalled deals effectively, re-engage prospects with empathy and value, and ultimately move toward successful outcomes.