Enhance Your Sales Pipeline with Expert Insights from ChatGPT
by Michael Hoffman

I reached out to a supplier recently to respectfully decline their offer. In the spirit of professionalism, I provided a rationale for our decision and left the door open for future opportunities. The reply I received was predictably intense—Eric (a pseudonym) had already displayed a forceful sales approach during our initial call. He was polished and aggressive, and after our conversation, when I commended his salesmanship, he quipped, “I haven’t sold you anything yet.” This gives you a flavor of his style.

Upon reading his charged response, I reflected on how I prefer to handle such situations. I believe in not souring a potential relationship due to a single negative interaction. I maintain this stance for two key reasons:

  1. Negativity offers no value and gains no ground, especially with potential partners.


  2. Valuable insights often emerge from customer feedback, once the initial disappointment settles.


Lately, I’ve been leveraging ChatGPT to fine-tune my emails, ensuring they’re courteous, proactive, and open to future endeavors. (Our collaborative efforts are detailed in a book I can share with you.) I input my email draft and simply command ‘Improve.’ More often than not, ChatGPT suggests enhancements that foster better engagement.

Eric might benefit from this tool. If he were to temper his responses through such an analysis, it could well transform his sales pipeline.


Here’s what I wrote:

Hi Eric,

After consulting with my Board of Directors, we’ve decided to temporarily hold off on moving forward. The reason is clear: while our landing pages are attracting a high volume of traffic, the conversion rate isn’t meeting our expectations. We’re prioritizing efforts to enhance our landing pages to ensure a minimum of a 15% conversion rate from visits to workshop registrations. Once we achieve this benchmark, we’ll be in a better position to revisit this project.

Thank you for your understanding and all the work you’ve put in thus far. I look forward to reconnecting in the near future.

Warm regards,

Michael Hoffman


Here is the response I received:

Hi Michael. How do you plan on effectively increasing your conversion to 15%?? With respect, no website I have tracked in my 7 years here converts at 15%… Sorry, but this just seems totally disjointed. Either I have not shown you how I can help you now, or this product has been totally misunderstood.

Here is how we help resolve the problem you have outlined below.. ‘the conversion rate isn’t meeting our expectations. We’re prioritizing efforts to enhance our landing pages to ensure a minimum of a 15% conversion rate from visits to workshop registrations’ You plan on trying to increase conversions with ZERO visibility?

This is absolutely impossible as you have no idea what is working and failing. You cannot measure what is driving the ideal companies to the website. It is however potentially possible IF you know what companies are coming to the website/landing pages in the first place. Then having the ability to change and alter your marketing to ensure you drive the relevant traffic that is likely to enquire.

Fact is though, no matter how good you think your website is, most visitors will not convert…this is where tracking, re-targeting and converting comes from our solution. Oliver Roberts Outbound Sales Director.


ChatGPT’s analysis

Analyzing Oliver’s response reveals a few pitfalls that are common in sales communication:

  1. Doubting the Client’s Goals: Oliver expresses skepticism about the 15% conversion goal, which could come off as dismissive. It’s generally not a good idea to start with a negative assumption about a client’s objectives; this can undermine the client’s confidence and could be perceived as disrespectful.


  2. Lack of Empathy and Understanding: The tone of the email might be perceived as condescending (“Sorry, but this just seems totally disjointed”). Sales communication should be empathetic and aligned with the client’s perspective to build trust and rapport.


  3. Assuming a Lack of Knowledge: The statement “You plan on trying to increase conversions with ZERO visibility?” assumes a lack of understanding on the client’s part, which can be off-putting. It’s more effective to ask questions to gauge the client’s awareness and strategies.


  4. Hard Selling Instead of Consulting: Oliver pushes the product as the only solution without acknowledging or building on the client’s strategy. A consultative approach that complements the client’s plans is often more effective.


  5. Negative Framing: The use of negative statements (“Fact is though, no matter how good you think your website is, most visitors will not convert…”) can create a defensive response. It’s more persuasive to focus on how the product can add value to what the client is already doing well.


In sales, it’s essential to listen actively, build on the client’s strategies, and position your product as a value-add rather than a necessity due to the client’s shortcomings. Oliver’s approach could benefit from more tactful language, a focus on collaboration, and a clear demonstration of how the product can support Michael’s goals.


Me: What might Eric have written?


Oliver could have written a response that acknowledges Michael’s goal, offers support, and gently presents the value of his service without undermining Michael’s current strategy. Here’s an example:

Hi Michael,

Thank you for sharing your objectives regarding the landing page conversion rates. Achieving a 15% conversion is certainly ambitious, and I admire your team’s commitment to setting high standards.

I understand the importance of enhancing your landing pages and would love to support your efforts in any way I can. While you’re focusing on improvements, I believe there’s an opportunity for us to help illuminate the path forward by providing insights into the behavior of companies visiting your site.

Our tools could offer the visibility necessary to fine-tune your strategy, ensuring that your enhancements are data-driven and directly addressing the needs of your visitors. We can identify not just the volume but the quality of your traffic, which might be the key to not only meeting but exceeding your conversion goals.

Please consider us a resource as you work towards this milestone. If you’re open to it, I’d be glad to discuss how we can complement your efforts with actionable data without any commitment on your part. Whenever you’re ready to discuss further, I’m here.

Best regards,


Outbound Sales Director

This approach is more supportive and collaborative, aligning with Michael’s goals while positioning Oliver’s product as a beneficial tool rather than a necessity due to a shortfall in Michael’s strategy.

Utilizing ChatGPT could significantly enhance your customer relations and bolster your sales pipeline. The key lies in the willingness to listen—a virtue that often remedies the core issues at hand.

Book a short call or learn more and register for the workshop here.

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