The Secret to AI is the Key to Better Sales Calls

In early 2023, sales professionals worldwide logged into ChatGPT for the first time with the expectation that they’d never have to write sales messaging themselves again.

Only, our first attempts resulted in messaging full of the competitor’s language; messaging that exaggerated our products/services; messaging that was too generic in its personalization to prompt any reasonable response.

Where did we go wrong?

We forgot one crucial fact that’s as true for AI as it is for any sales conversation: the quality of the result depends on the quality of the prompt.

When it comes to generative AI, we’ve all learned that a generic prompt renders a generic result – and the same holds true for your sales calls:

  • We now know that “A yellow owl flying.” ≠ “A sketch of a yellow owl flying over a mysterious castle in the style of Gothic art.”
  • Why do we continue to make the mistake of thinking, “What is your department working on these days?” = “After hearing your CEO speak at Dreamforce, I know that the company’s top priorities are reinforcing your commitment to improving profitability and driving innovation in machine learning and cloud-connected technologies – how does this affect your role?”

With this in mind, let’s look at a time-tested method for prompting your customers to give you the kind of responses that move deals forward.


The Mindset for Effective Sales Calls

Think back to when you first started in sales – you were taught to identify a prospect’s problem and explain how your product was the solution, right? It’s the classic sales pitch.

While this approach can still work from time to time, it’s lacking a crucial component: the differentiation that motivates the prospect to purchase from you instead of someone else.

The key to becoming a trusted business advisor, rather than merely a seller, is to uncover the prospect’s view of the ideal solution, what solutions they’ve tried and the results, and what they liked/disliked about various approaches.

When you fully understand the problem and what the prospect desires in an ideal solution, you can position your product as a collaborative solution. Suddenly, you no longer have what the prospect needs, but you have exactly what the prospect has told you they need.

Identifying Business Issues

Of course, to facilitate the customer’s problem-solving experience on this level, you’ll need to guide them to identify their issues and uncover a problem worth solving: a business issue.
Business issues represent the reason organizations seek solutions – and they typically fall into three major categories: revenue growth, cost savings and regulatory compliance.

To uncover business issues, begin with open-ended questions that showcase your familiarity with the prospect’s situation and your interest in helping them. In fact, the example I used in the opening of this article is a good example of an open-ended question you might use early in the sales process:

After hearing your CEO speak at Dreamforce, I know that the company’s top priorities are reinforcing your commitment to improving profitability and driving innovation in machine learning and cloud-connected technologies – how does this affect your role?

Once you’ve learned about the context behind those changes and how they impact the individual you’re speaking to, you can shift the conversation to understand their perspective on possible solutions better:

When you think about increasing data-sharing capabilities across teams, what do you hope will change?

Remember that the true power of the O-P-C Questioning technique is to move seamlessly between open-ended, probing and confirming questions:

  • Open-ended questions like the above get the prospect talking and help them to examine their thinking – providing you with critical insight into their ideal solution.
  • Probing questions are close-ended questions you can use to challenge a prospect’s thinking without creating friction and gain increased insight into how they prioritize problems – enabling you to re-order these so that the problems you can uniquely solve are at the top of the list.
  • Confirming questions are for building rapport and testing your accuracy. Here’s where active listening pays off. Remember to mirror the prospect’s terminology when confirming business issues and motivations.

How Good Questions Help You Close Sales

As we settle into Q4, the need to close the quarter and the year strong looms large. During this chaotic time, it’s all too easy to overlook one fact: closing sales is the natural conclusion to an effective sales process.

When deals stall in Q4, it’s because something was missed earlier in the sales cycle, and the best way to avoid this is to develop a strong mutual plan with your prospects – and it’s effective questioning that lays the foundation of any mutual plan. Now’s the time to review your mutual plans with prospects to ensure you’re still in alignment. And if things are out of sync, you can use your questioning process and this checklist to investigate where the misalignment occurred.


In closing, I want to address the elephant in the room: AI. Yes, it’s exciting; yes, it will change our profession; and no, it will not replace our greatest asset: our salespeople. There is one thing I know for sure: AI cannot replicate the magic of the experience provided by a skilled, authentic and talented salesperson who genuinely partners with customers to facilitate their success.
For more selling advice, check out:

As always, Sell with Value,


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