Hey there, it's Nishit, co-founder of Sybill.

If you are a seller, you know there’s no concept of ‘being over-prepared for a sales call’. Especially one with a potential detractor, who would rather move on to more “important” blocks on their calendar than talk to you.

In this article, I dive into how I prepared for an important call with a VP of IT using ChatGPT-4o to roleplay with me. It was refreshingly smart, and the audio interface made it surprisingly real.

But first, why’s an AI-powered roleplay even important?

I’ve done tons of founder-led sales. Nothing prepares you for a difficult conversation  as much as having a similar difficult conversation .

Nothing ramps reps faster than a true roleplay - barring them getting into a sales call themselves and burning crucial leads.

But your manager or coworker isn’t always around to help with roleplay, and when they are, it’s not always easy for them to accurately play your target persona. Whether you’re nervous before a call or just want to be prepared for anything, ChatGPT (and other LLMs with a voice interface) is a solid practice partner.

Now let’s get to the meat of it - here’s how I created a simple but comprehensive prompt to get ChatGPT started. And boy, did it carry the conversation!

Breaking down the prompt

To make the most of the roleplay, I included some key details in the prompt:

• Who I’m talking to: Provide a quick background on the customer, like their role, industry, and any relevant details.
• Customer's personality and potential objections: Describe the customer’s typical concerns, objections, and personality traits.
• My product details: Share a brief description of your product, in my case, it was of course Sybill, and focus on the key features and benefits.
• Reason for the call: Explain the objective of the conversation, what you hope to achieve, and the relevant context.
• Roleplay instructions: Outlined how I wanted ChatGPT to engage with me during the roleplay—whether I wanted tough objections, a cooperative tone, or any such specific scenarios.

The prompt:

• Who I’m talking to:“I’m going to be talking to a Vice President of Information Technology (VP of IT) at a mid-size SaaS company (250-500 employees) based out of San Francisco. He has previously been in IT and DevSecOps leadership roles at startups and scale-ups in the Bay Area, and has a reputation for adopting new technologies as they come. He has been an early adopter of some innovative SaaS products in the past, helping his team members in HR, Ops, legal, and sales test out new products and adopt game-changing tech before it gets mainstream.
• Customer's personality and potential objections:However, he is also a sound critical thinker, doesn’t shy away from asking hard questions, and can raise major objections related to setup, security, and integrations of our product.
• My product details:Here’s a blurb about our product: Sybill is an AI assistant for sales reps, and our website is at https://www.sybill.ai. It helps remove busywork from sales reps' lives and bring the voice of the customer to the entire company. Sybill currently automates the following workflows: taking notes during meetings, producing elegant and detailed meeting summaries, and sharing them with the relevant stakeholders on email, Slack, and CRM; drafting follow-up emails using AI based on the meeting content and the user’s tone of voice; and automatically pushing notes into the CRM for various sales methodologies corresponding to deal qualification including MEDDIC, BANT, SPICED, etc., also next steps, tech stack, and product gaps, etc. This enables unparalleled visibility for sales leadership and spreading the voice of the customer across the entire org.
• Reason for the call:The reason why I’m going on a call with this VP of IT is the following: we’ve had a chat with a couple of sales reps in their company who initially started using our product in the free trial, and loved it. They then brought in their manager, who was curious to explore and asked us if we could extend the trial, and she would bring on her IT leader (without whose permission more of the org can’t adopt the tool) and her VP of Sales in the conversation. We agreed to that proposal, and now have a call with this IT leader, and the sales manager will be on the call as well.
• Roleplay instructions:The IT leader could block the deal from moving forward or could become a supporter - depending on this call and our follow-up after that.
  
  Lastly, I want you to roleplay this conversation with me. I will start the conversation and you then continue, ask me hard questions, be skeptical, but also embody the innovative personality of the IT leader. We'll run this for 5 rounds of exchange in the conversation (where 1 round is a back-and-forth between me and the IT leader). Okay? I'll start the conversation after you respond to me with "okay".
  

Simple, right?

Just go to ChatGPT-4o, enter the prompt in the message section, and you're all set.

This is how real it got with the new voice feature:

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I did this roleplay with ChatGPT and ran it for a few more iterations with tweaks. It helped me prepare for the most common objections, identify my weak spots, and make sure I addressed them prior to the call.

So, there you have it. With prompts like these, it’s easy to get ChatGPT to roleplay with you. Just make sure to include all the important details. You can tweak it for any situation, whether you’re handling objections, practicing your pitch, or testing out new strategies.

Have fun with it, good luck, and stay tuned for more such hacks! Do let us know if you have any feedback, if you found this useful, and if there are any specific topics that you’d like us to write about.

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