August 29, 2024
Nishit Asnani
Hey there! Nishit here, co-founder of Sybill.
Just yesterday, I was on the brink of losing a $15k deal that was almost closed.
Out of nowhere, the VP of Sales hit me with a last-minute objection—worried about a competitor’s feature he thought might be a deal-breaker.
He wasn’t moving forward until every concern was addressed. But instead of panicking, I saw it as a golden opportunity.
I took a deep breath, and thanks to all the roleplaying I’d done with ChatGPT, I was ready. I countered the comparison, showcased Sybill’s unique value, and by the end, he was totally sold 😉.
I don’t just roleplay—I let ChatGPT rate my performance and throw in some improvement tips. It’s like having a personal sales coach who is available 24*7.
In my last post, I talked about how to started with ChatGPT to roleplay sales calls. Today, let’s dive into how it can help with objection handling.
Objection handling is where deals are made or broken. It’s not just about answering questions. It’s about building trust, showing off your product’s value, and steering the conversation to a close. Whether you’re pitching to startups or big-name companies—mastering objections is key.
Here’s how I use ChatGPT to practice it every now and then:
Start by providing ChatGPT-4o a solid prompt. Make it as detailed and contextual as possible—think of it like briefing a real person.
Include everything: the client’s background, their personality, what they care about, and, of course, the specific concerns they might have. The more context you provide, the more realistic and helpful the roleplay will be.
Here’s an example:
I’m talking to the VP of Sales at a mid-size SaaS company. We’ve had several demos and discussions, and he was ready to move forward until he raised a last-minute objection about a feature comparison with a competitor. He’s detail-oriented and won’t make a decision until every concern is addressed. His main worry is about a competitor feature that updates relevant CRM fields after every conversation with the client, which he thinks might be a deal-breaker since they are considerably cheaper. My goal is to overcome this objection and emphasize Sybill’s overall value to move the deal forward.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, but also embody the innovative personality of the Sales 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 Sales leader). Okay? I’ll start the conversation after you respond to me with "okay.”
Now, it’s game time. Get into a 1:1 with ChatGPT, which is now playing the role of your skeptical prospect. Respond to the objections just like you would in a real sales call. This is your chance to test out your best arguments, tweak your messaging, and see what sticks.
This is how it may look:
Once you’ve wrapped up the roleplay, don’t just walk away—ask for feedback. ChatGPT can rate your objection handling, break down each of your arguments, and give you detailed feedback on what worked and what didn’t. Plus, it can toss in some best practices to keep you on your A-game.
A snippet of how ChatGPT rates your arguments:
Now that you’ve got feedback, it’s time to rinse and repeat. Run another roleplay, refine your approach, and keep sharpening your skills. The more you practice, the more natural and confident you’ll feel when the real objections roll in.
Mastering objections isn't just about knowing the right answers; it's about building confidence and credibility. With each practice session, you're not just sharpening your skills—you're preparing yourself to turn every objection into an opportunity. So, suit up, dive into ChatGPT roleplays, and get ready to close deals like a pro. Your next big win could be just one objection away!
Hey there! Nishit here, co-founder of Sybill.
Just yesterday, I was on the brink of losing a $15k deal that was almost closed.
Out of nowhere, the VP of Sales hit me with a last-minute objection—worried about a competitor’s feature he thought might be a deal-breaker.
He wasn’t moving forward until every concern was addressed. But instead of panicking, I saw it as a golden opportunity.
I took a deep breath, and thanks to all the roleplaying I’d done with ChatGPT, I was ready. I countered the comparison, showcased Sybill’s unique value, and by the end, he was totally sold 😉.
I don’t just roleplay—I let ChatGPT rate my performance and throw in some improvement tips. It’s like having a personal sales coach who is available 24*7.
In my last post, I talked about how to started with ChatGPT to roleplay sales calls. Today, let’s dive into how it can help with objection handling.
Objection handling is where deals are made or broken. It’s not just about answering questions. It’s about building trust, showing off your product’s value, and steering the conversation to a close. Whether you’re pitching to startups or big-name companies—mastering objections is key.
Here’s how I use ChatGPT to practice it every now and then:
Start by providing ChatGPT-4o a solid prompt. Make it as detailed and contextual as possible—think of it like briefing a real person.
Include everything: the client’s background, their personality, what they care about, and, of course, the specific concerns they might have. The more context you provide, the more realistic and helpful the roleplay will be.
Here’s an example:
I’m talking to the VP of Sales at a mid-size SaaS company. We’ve had several demos and discussions, and he was ready to move forward until he raised a last-minute objection about a feature comparison with a competitor. He’s detail-oriented and won’t make a decision until every concern is addressed. His main worry is about a competitor feature that updates relevant CRM fields after every conversation with the client, which he thinks might be a deal-breaker since they are considerably cheaper. My goal is to overcome this objection and emphasize Sybill’s overall value to move the deal forward.
I want you to roleplay this conversation with me. I will start the conversation and you can then continue, ask me hard questions, be skeptical, but also embody the innovative personality of the Sales 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 Sales leader). Okay? I’ll start the conversation after you respond to me with "okay.”
Now, it’s game time. Get into a 1:1 with ChatGPT, which is now playing the role of your skeptical prospect. Respond to the objections just like you would in a real sales call. This is your chance to test out your best arguments, tweak your messaging, and see what sticks.
This is how it may look:
Once you’ve wrapped up the roleplay, don’t just walk away—ask for feedback. ChatGPT can rate your objection handling, break down each of your arguments, and give you detailed feedback on what worked and what didn’t. Plus, it can toss in some best practices to keep you on your A-game.
A snippet of how ChatGPT rates your arguments:
Now that you’ve got feedback, it’s time to rinse and repeat. Run another roleplay, refine your approach, and keep sharpening your skills. The more you practice, the more natural and confident you’ll feel when the real objections roll in.
Mastering objections isn't just about knowing the right answers; it's about building confidence and credibility. With each practice session, you're not just sharpening your skills—you're preparing yourself to turn every objection into an opportunity. So, suit up, dive into ChatGPT roleplays, and get ready to close deals like a pro. Your next big win could be just one objection away!
