Episode #360: Ollie Whitfield

Reframe Your Thoughts with ChatGPT to Improve Sales Engagement
Ollie Whitfield


Ollie Whitfield

Ollie is a marketing leader with a passion for cold email. When he’s not on Zoom or Teams, he’s perfecting his craft on the pool table. No 9 ball, all 8 ball!

Our Mission Is To Change The Negative Perception Of Sales People

Our Vision Is A World Where Selling Is A Profession To Be Proud Of

You can ask ChatGPT anything. And anyone can apply it in their field. But most salespeople just don’t know how to leverage it. Ollie Whitfield believes that self-awareness allows you to fully utilize ChatGPT. How? 

It can help you improve your emails, rewrite cold-calling scripts, and even summarize notes. ChatGPT can reframe your thoughts in a more succinct and engaging way. Ollie shares how he uses this to his advantage in this episode of Sales Reinvented! 

Outline of This Episode

  • [0:41] How can ChatGPT enhance the sales process?
  • [2:01] Key features and capabilities of ChatGPT
  • [3:19] How ChatGPT can help with prospecting
  • [5:41] Ollie’s ChatGPT success story
  • [7:18] The challenges or limitations of ChatGPT
  • [9:56] How ChatGPT handles personalization
  • [12:05] Ollie’s top three ChatGPT dos and don’ts
  • [15:00] Use Chat GPT to summarize notes

How ChatGPT can help with emails

Ollie can write a decent email himself. But he struggles with saying everything too quickly. He might offer three value propositions in the first email and have nothing left to say. So he uses ChatGPT to break down points, trigger events, etc. to hit on. He also asks chatGPT to reframe his email. Ollie typically uses the AIDA framework when writing emails:

  • A = Attention
  • I = Interest
  • D = Desire
  • A = Action

Sometimes, he’ll ask ChatGPT to translate his email into another framework. It can change the length shorter or longer, change it to a story, etc. It gives Ollie a different cadence. If you know someone’s personality type, you can choose the right framework to change your email/communication to.

You can also take transcriptions and recordings, plug them into ChatGPT and say, “Hey, here are the summary points I think I heard. Is that correct?” It helps him land heavier punches in prospecting.

Use ChatGPT to reframe your thoughts

Ollie likes recording videos. He scripts them well and comes across with an animated tone and pitch. Sometimes he’ll ask ChatGPT to rewrite his script or redo the framework. He’s tried it a handful of times and often gets better engagement from the prospect.

Sending videos to prospects is still a novelty, but most people frame their highlight reel the same way. So anytime you can mix it up, it makes a difference. Ollie asks ChatGPT to rearrange what he’s saying to stand out.

Ollie’s top three ChatGPT dos and don’ts

ChatGPT isn’t quite plug-and–play. Sometimes you’ll get outputs that aren’t applicable. If you ask it to write an email, it doesn’t have the context to know what’s current best practice. That’s why the quality of the prompt is key. Ask it something specific that’s a hole in your own workflow. You must provide the context. What are some other dos and don’ts? 

  • Don’t copy and paste what it says. If you ask it a bland question, you’ll get a bland result—that will get you bland results. 
  • Don’t ask it to do something that only you could do. If your special skill is video, don’t ask it to do a video script. Use it to cover your weaknesses. 
  • Don’t tell a prospect that you used ChatGPT to write the email unless they mention it and they’ll think it’s funny. 
  • Do carve out time to play around with the AI. Sit down and work out how to use it in your process.
  • Know what you want ChatGPT to do for you and give it the specifics it needs to yield the results you need. 
  • Tell other people how you’re using ChatGPT. It will help you learn how else you can use it. 

Why not share with your colleagues and coworkers? Selling is a team sport. Share your best practices. 

Use Chat GPT to summarize notes

Many salespeople don’t like physically taking notes. It takes time and they want to give their prospect their full attention. So they record their meetings. Ollie was notetaking a “here are the next steps” meeting and ChatGPT helped him distill down the list of complicated setups. 

When another decision-maker joined the buying committee and had to be brought up to speed, Ollie took all of his notes, input them into ChatGPT, and asked it to summarize what had already been talked about. It can’t help with everything but if you ask it to do something specific it can go narrow and deep. 

How else can you leverage ChatGPT to help you get better results? Listen to the whole episode to learn more! 

Resources & People Mentioned

Connect with Ollie Whitfield

Connect With Paul Watts


Audio Production and Show notes by

Learn More About Ollie Whitfield

Are there any resources on or ChatGPT that you recommend? The Lex Fridmann podcast is very interesting. Lex is a data scientiest who is very interested in AI and speaks to (mostly) leaders in the space. Zuckerberg, for example. If you want to understand more broadly what are AI’s doing in the world right now beyond the main one which we all know, this is a good place to start.

In the field of AI and Sales – Who do you most admire and why? I can’t say I have found one person in particular I am paying attention to more than others. If anything, most people discussing this are working on their own projects which they are talking about in the main. That is why I go to outside podcasts with more general themes like the Lex Fridmann show.

What are your top ten favorite prompts in ChatGPT – Your Golden Question/Prompt Set? I often ask ChatGPT to respond with various themes and styles which is how I generate very different responses to the same question. Of course, it is not emotional but you can ask it to imitate and behave alike someone or something. I use several contrasting emotions and styles as I continue the same thread and ask it to iterate to fully expose a broader point of view on the same topic.

What are some of the most important considerations that companies should aware of as it relates to their employees usage of ChatGPT? Copying and the ease of use. The very last thing you want to do is use the tool to write a super personalized email which is directly copied, and the reader finds out. All credibility is gone, you’re getting deleted and they don’t ever trust you again. 

Should training be provided for employees to utilize this tool safely and effectively and should this be included in a salespersons induction / onboarding process? Now, yes. Though the challenge will and is currently the training content and who can teach it. Training programs need to be official and curated, with anything new it is hard to generate and authenticate the content. Especially as AI changes so incredibly fast.

Can you share some examples of how ChatGPT has helped companies improve their sales process or increase sales. Most are using it to help them with their cold outreach. And many are starting to use it to help remove admin work in sending post-call notes and summaries. Transcribing and asking for summaries is a big time save and helps sales reps get back to selling. We’re all aware of that crazy statistic where around 70% of the time rep’s have at work is not spent actually selling. This is one other way they can claw back some of that time. 

Are there any aspects of your own ChatGPT skills that you are working on improving at the moment? Me personally, I want to try and tweak my responses so that they sound a little more like something I would write. My personal tone for written communication is very casual, which it hasn’t mastered when prompted to try and emulate. 

Hobbies, Interests? Pool, pool, pool, pool. 

How can our listeners contact with you? Ask ChatGPT. Kidding, LinkedIn is always the place but I am also trying out Threads. 

by | Jul 26, 2023 | Sales Reinvented Podcast

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