In Closing Moves – Inside Brian’s Deal-Winning Playbook, trumpet CEO Rory Sadler, CEO of trumpet, and Brian LaManna, Enterprise AE at Gong, about how real relationships and sharp discovery create deals that actually close.
One thing Brian doesn’t do? Treat prospects like pipeline entries.
Personal before professional
Brian explains why human connection makes the difference:
“Get to know them on a human level… like if they had weekend plans or it’s their son’s first birthday, send a GIF or a meme. Treat them like more than just your prospect in a piece of your deal.”
Instead of surface-level rapport, he creates trust that leads to honesty, access and momentum.
Come in with a point of view
Discovery isn’t about generic questioning, and Brian avoids starting with “What are your top priorities?” He shows he’s done the thinking:
“I reference really specific observations… I saw the team launched a new product or expanded into Dublin. I’d imagine X, Y, Z is top of mind.”
From there, he peels back further and revisits it as the deal progresses.
Ask questions that surface real priority
Once you have context, tough questions expose urgency:
“If we haven’t improved sales for that in the next 90 days, is that okay, or is that something you wanted solved yesterday?”
Those answers tell you whether your solution is tied to a real business need, or just sitting in the "maybe" pile.
At its core, Brian’s approach is simple:
✅ Be human
✅ Come with a point of view
✅ Ask the kind of questions AI won’t
FAQ
Why does personal connection matter in enterprise sales?
It builds trust, creates access to stakeholders and makes champions more invested in moving the deal.
What is a point-of-view-led discovery call?
It means coming prepared with researched assumptions instead of asking generic openers, which leads to deeper conversations.
How do tough questions help deals progress?
They test urgency, surface real priorities and stop deals from slipping into “no decision”.
Head here to watch the full webinar
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