The Gen AI Sales Prompt Series: Share ten effective strategies for B2B account managers to win back a lost client

AI Editors, Sales 3.0 Conference

A man standing in a red jacket looks out over a tundra landscape.

For the prompt, Share ten effective strategies for B2B account managers to win back a lost client, we put three leading Gen AI Chatbots to the test. If you’re using another chatbot, put yours to the test!

Result Comparisons

Chat GPT

  1. Conduct a Thorough Post-Mortem Analysis
  • Objective: Understand why the client left.
  • Actions: Gather feedback from both your internal team and the client. Analyze the issues and identify root causes. This could involve product or service shortcomings, communication issues, or pricing disagreements.
  1. Personalized Communication
  • Objective: Rebuild the relationship on a personal level.
  • Actions: Reach out directly through personalized emails or phone calls. Show empathy and genuine concern for their departure. Acknowledge past issues and express your commitment to addressing them.
  1. Offer Tailored Solutions
  • Objective: Address specific needs and pain points of the client.
  • Actions: Develop customized solutions or packages that directly respond to the problems that led to their departure. Highlight how these new solutions are different and better.
  1. Provide Incentives
  • Objective: Make the return appealing and beneficial.
  • Actions: Offer discounts, extended payment terms, or added value services as incentives for returning. Ensure these incentives are significant enough to show your commitment to winning them back.
  1. Enhance Product or Service Quality
  • Objective: Show improvements and innovations.
  • Actions: Demonstrate any enhancements in your products or services since their departure. Provide case studies or testimonials from other clients to show the tangible benefits of these improvements.
  1. Strengthen Support and Communication Channels
  • Objective: Improve client support and communication.
  • Actions: Implement more robust customer support systems, such as dedicated account managers, regular check-ins, and quicker response times. Clear and proactive communication can help rebuild trust.
  1. Leverage Existing Relationships
  • Objective: Use mutual connections to re-establish trust.
  • Actions: If possible, use common contacts or industry connections to facilitate re-engagement. Testimonials or recommendations from trusted sources can be highly influential.
  1. Conduct a Competitive Analysis
  • Objective: Understand the competition’s advantage.
  • Actions: Identify what competitors are offering that you might not be. This can inform your approach to offer something unique or match and exceed their offerings.
  1. Showcase New Business Successes
  • Objective: Highlight your company’s growth and stability.
  • Actions: Share recent successes, new clients, industry awards, or significant developments in your company. This can help rebuild confidence in your capabilities.
  1. Offer a Trial Period
  • Objective: Reduce the perceived risk of returning.
  • Actions: Provide a no-obligation trial period or a pilot project. This allows the client to experience your improved offerings firsthand without a long-term commitment.


  1. Analyze the situation: Understand the reasons why the client left in the first place. Was it due to poor service, lack of communication, pricing issues, or something else? Identifying the root cause is crucial for addressing the problem.
  2. Reach out and listen: Contact the former client and arrange a meeting or call. Listen actively to their concerns, complaints, and feedback without getting defensive. Acknowledge their perspective and show genuine interest in understanding their point of view.
  3. Take responsibility: If there were missteps or mistakes on your part, take responsibility for them. Apologize sincerely and demonstrate that you have learned from the experience and have implemented measures to prevent similar issues from occurring in the future.
  4. Offer a solution: Based on the feedback received, present a comprehensive solution that addresses the client’s specific concerns and needs. Outline how you plan to rectify the issues and provide a better experience moving forward.
  5. Highlight improvements: Share details about any changes, upgrades, or enhancements you have made to your products, services, or processes since the client left. Demonstrate your commitment to continuous improvement and how these changes can benefit the client.
  6. Provide added value: Offer incentives, discounts, or additional services that could sweeten the deal and make it more attractive for the client to return. However, be cautious not to over promise or under deliver.
  7. Leverage relationships: If you had strong personal relationships with key stakeholders within the client’s organization, leverage those connections to help facilitate the reconciliation process.
  8. Set realistic expectations: Be transparent about what you can and cannot deliver. Manage expectations from the outset to avoid any misunderstandings or disappointments down the line.
  9. Follow up consistently: Winning back a lost client may require persistent, yet respectful, follow-up efforts. Stay in touch, provide updates, and demonstrate your commitment to rebuilding the relationship.
  10. Learn from the experience: Regardless of the outcome, use the experience as a learning opportunity. Identify areas for improvement within your organization and implement changes to prevent similar client losses in the future.

Microsoft Copilot

  1. Ask for Feedback: First and foremost, you can’t win back previous customers without knowing why they left. Reach out to them and ask for honest feedback. Understand their pain points and address them proactively.
  2. Provide Exceptional Customer Service: Poor customer service is a top reason why businesses lose clients. Ensure that your team delivers exceptional service. Go above and beyond to meet their needs and expectations.
  3. Offer Rewards for Customer Loyalty: Incentivize returning clients by offering loyalty rewards. Whether it’s discounts, exclusive access, or personalized perks, make them feel valued and appreciated.
  4. Add Value: Demonstrate the value your product or service brings. Highlight any improvements, additional features, or benefits that might have been introduced since they left.
  5. Communicate with Your Customers: Regular communication is essential. Keep them informed about updates, new offerings, and relevant industry insights. Show that you care about their success.
  6. Refresh Your Brand’s Image: Sometimes a fresh perspective can reignite interest. Update your branding, messaging, and positioning to capture their attention again.
  7. Offer Financing Options: Financial flexibility can be a powerful motivator. Provide payment plans or financing options to ease their decision-making process.
  8. Offer Upgrades or New Products: Showcase any enhancements or innovations in your product line. Position these as solutions to their pain points or business challenges.
  9. Leverage Key Relationships in the Account: Strengthen relationships with key stakeholders within the client’s organization. Personal connections can play a significant role in winning them back.
  10. The “Phoenix Approach”: Imagine your lost client as a mythical phoenix—a majestic bird that rises from its own ashes. Here’s how you can apply this approach:
  • Acknowledge the Past: Begin by acknowledging any mistakes or missteps that led to the client leaving. Be honest and transparent. Sometimes, admitting fault can be the first step toward rebuilding trust.
  • Reignite Curiosity: Like the phoenix, spark curiosity. Send them personalized content—perhaps a thought-provoking article related to their industry or a case study showcasing your recent successes. Make them wonder what they’ve been missing.
  • Customize Your Offering: Tailor your proposal specifically to their needs. Show them that you’ve put thought into addressing their pain points. Highlight how your product or service aligns with their unique challenges.
  • Create a Sense of Urgency: The phoenix rises swiftly. Use urgency to your advantage. Offer a limited-time discount or an exclusive deal. Make them feel that now is the perfect moment to return.
  • Rekindle Personal Connections: Reach out personally. A heartfelt email or a phone call can go a long way. Remind them of the positive interactions you’ve had in the past. People remember how you made them feel.
  • Offer a Trial Period: Give them a risk-free opportunity to experience your product or service again. Offer a trial period with no strings attached. Let them see the improvements you’ve made.
  • Celebrate Their Return: When they do come back, celebrate it! Send a welcome-back gift or a handwritten note. Make them feel like a valued part of your business family.

Remember, the “Phoenix Approach” is about rising stronger together. Adapt these steps to your specific situation, and may your lost clients return like mythical birds with renewed enthusiasm!