*This episode was recorded during our Soundcheck days — now proudly rebranded as GTM Insider.

TL;DR

• Don’t just ask back-to-back questions—respond to what buyers say and create a true dialogue.

• The faster you talk, the more pressure buyers feel. Slow down and focus on tone and pacing.

• Do your research before the call. Skip obvious questions and get straight to the value.

• Show part of the product in the first call—it builds trust and saves time.

• It’s OK to give a pricing range early. Buyers appreciate transparency.

• Let blunt or closed-off buyers talk more. Most open up if they feel heard and in control.

• Self-deprecating humor and relatability humanize you and help reduce sales resistance.

• You don’t need instant rapport. Focus on being real, relevant, and respectful of their time.

In this episode of The SoundCheck, Scott Leese—Fractional CRO, sales leader, author, and founder of multiple revenue communities—shares his blueprint for turning stiff, awkward sales calls into human-first conversations. He breaks down how to handle high-pressure calls, when to show your product, and why building trust starts with ditching robotic discovery playbooks.

Talk Less, Listen More

Scott says one of the fastest ways to feel like an interrogator is to fire off question after question without acknowledging the buyer’s answers. 'If I ask you something and then jump to the next thing immediately, it doesn’t feel like a conversation,' he explains.

Instead, he recommends slowing down, responding to what’s shared, and letting the discussion flow naturally—just like you would on a date or over a drink with a friend.

The idea that sales should feel less like an interrogation is explored further in our blog on Replace the B2B demo with a buyer-led journey.

Do Your Homework

'It’s frustrating when a rep asks me something they could’ve Googled,' Scott says. Knowing the basics before the call—like company size or what tool they use—allows you to skip ahead to the value-led part of the conversation.

Scott’s advice mirrors what we covered in our post on The psychology of modern buyers.

Don’t Gate the Product

Scott challenges the old rule that you should never show the product on the first call. 'If you’ve uncovered a need, show them something—just a taste,' he says.

With Trumpet’s digital sales rooms, you can give prospects a look at the product experience early—without losing control of the sales process.

Talk Price Early (It’s Fine)

Waiting until the third call to mention pricing often backfires. 'It’s not a trap—just be real,' Scott advises.

If you're using Trumpet, you can confidently reference your transparent pricing to help buyers make faster decisions.

Let Quiet Prospects Talk More

Scott suggests flipping the ratio with guarded buyers: 'Let them talk 70% of the time... they'll associate you with that positive experience.'

This strategy is made easier with real-time insights from your buyer engagement analytics.

Use Humor and Humanity

'I make fun of myself a lot,' Scott says. Self-deprecating humor humanizes the rep, lowers buyer defensiveness, and invites authenticity on both sides.

Rapport Isn’t Instant

Forget trying to build deep relationships in 15 minutes. 'You earn that over time—through relevance, helpfulness, and showing up consistently,' Scott explains.

Post-call collaboration with mutual action plans gives buyers clear next steps—without the pressure.

Final Thought: Make Sales Feel Human

The best sellers today don’t follow rigid scripts—they start real conversations. Scott’s approach is a reminder that buyers don’t want to be handled; they want to be heard.

By slowing down, staying human, and showing value early, you create the kind of trust that actually moves deals forward.

👉 Want to equip your team to run better, buyer-first conversations? Book a demo with Trumpet and see how we help modern reps make every interaction count.

‍

‍

‍