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Chris Duprey

By Chris Duprey

Oct 4, 2023


Sales & Marketing Technology Sales Professionals Artificial Intelligence
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Sales & Marketing Technology  |   Sales Professionals  |   Artificial Intelligence

The Future of Sales Training: Using AI to Develop Your Approach

Chris Duprey

By Chris Duprey

Oct 4, 2023

To many sales professionals, role-playing makes them think of awkward therapy sessions or that famous scene in The Office where Jim has some fun with Dwight.

And I get it. I understand why this topic prompts so many cringes and eyerolls. Role-plays can be awkward and uncomfortable, but, when done right, role-plays are an invaluable tool for improvement

Think about it: Wouldn’t you want to practice for an important conversation or meeting before you have it? 

Practice before money is on the line

For the sake of this discussion, let’s not think of it as role-plays per se, but as sales practice. Sales practice can occur in a variety of settings, but the frustrating truth is that it occurs far too little. 

Research shows that 58% of buyers say that sales reps can’t answer their questions effectively. In the B2B space, it’s even higher, with 82% of buyers reporting that sales reps are unprepared.  

And yet these unprepared sales reps are resistant to practice. But it’s not just our egos that are barriers to great practice. Practice takes time and commitment. 


Enter AI — a tireless sparring partner and ever-ready resource to help you improve.

Recently, I’ve been working with ChatGPT-4 as a practice partner, and I want to explain ways you can use it as well.

And, as with anything with AI, this topic comes with all the same caveats: Yes, AI can be biased. Yes, it can hallucinate. Yes, it’s not always going to be accurate. Yes, the responses can feel robotic.

But with all that said, AI is a tool that’s always ready to assist. And for salespeople, it can help you get the benefits of role-playing when you don’t have a human partner to practice with.

Here’s how:

Use AI to build your sales pitch

Got something to sell but not sure how to sell it? Use ChatGPT to develop a pitch based on the problems you solve. 


Note, I’ve long been an advocate of moving away from a traditional sales pitch, and that’s not what I mean here.

The modern sales pitch needs to be more about asking questions and listening than bragging about features. Even so, AI can help you develop those questions that really prompt a great conversation.

As for effective listening skills? There’s no machine that can help there — but there is communication training that can be an absolute game changer.

How I prompt ChatGPT-4:

Hey pal, I’ve got a second sales call with a company that does [insert details]. In our first call we discussed [insert the key points of the conversation]. In this call, I need to help them create some urgency to take action to solve their issues. Can you help me come up with a few great questions to drive urgency, without sounding like a needy salesperson?

Use AI to generate objections

If you’ve ever been asked a question by a prospect that’s made you squirm, you’ll remember that feeling forever. Maybe it’s about the price of what you sell. Maybe it’s about a negative review you received. 

And, we all know the feeling of turning a tough question into a great conversation. 

The most useful part of role-playing is practicing the way you answer questions. You want to anticipate objections and be ready to respond in kind. 

Go through your sales pitch with ChatGPT-4. Ask about objections or questions that could come up. Be on the lookout for things you hadn’t anticipated.

How I prompt ChatGPT-4:

Hey pal, I’ve got a sales call coming up and I want to be ready. I’m going to be talking to _______ company about [insert service]. Please review our service page [insert URL] and tell me what questions you’d have for me and what objections you may bring to the sales conversation. Act like [insert their buyer info] to do this. 

Use AI to evaluate a company’s website

If you’re in B2B sales, you’re booking calls with companies you don’t know much about. You can comb through web pages and LinkedIn profiles, but ChatGPT-4 can instantly scan a URL and get back to you with insights.

A website is how a business presents itself publicly — and it’s a goldmine for information about strategy, positioning, and culture.  

How I prompt ChatGPT-4:

Hey pal - please review this website [insert URL] and summarize what the company does and who its target audience is based on the content of the site. Now go to the service page [insert URL] and identify what questions you’d have as a potential buyer.

Use AI to review your last call

If you’re a sales rep with a healthy pipeline, you might have dozens of deals in progress at any given point. When you’re going into a second call with any given prospect, you need to remember how the last call ended. Meeting notes in your CRM are important, but AI can give you another refresher. 

Put the transcript from your last call into ChatGPT-4 and ask for:

  • A summary
  • Critical next steps and action items
  • Key questions asked by the prospect

Then, when you go into your next call, you’re up to speed and can demonstrate what appears to be impressive recall and attention. 

How I prompt ChatGPT-4:

Hey pal, I just had a sales call and want some help identifying action items, next steps, and the questions the buyer asked. I’d also like you to provide me what you think my actions should be, knowing I want to close this this month. Here is the transcript [insert transcript]:

Think of AI as your sales assistant

An AI tool like ChatGPT-4 is a powerful, competent assistant that can help you become your best self. 

For all the reasons stated above, sales reps need to practice to be at their best. While practicing with other humans is the most beneficial practice you can do, AI is a close second. 

Use it as a tool to help you stay sharp, anticipate objections, and always be ready for whatever questions your buyers pose.

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