A few months ago, I had a conversation with a sales rep who prided himself on his ability to move fast - quick dials, rapid pitches, closing like a machine. But then, he hit a wall.
He told me about a current prospect who spoke slowly. Not just “took a breath between sentences” but S.L.O.W.! This woman spoke with long, thoughtful pauses. “It was like pulling teeth,” he said. “I almost lost it.”
We talked through it as I watched the recording on zoom. I encouraged him to lean in, slow his own pace, ask fewer, but deeper, questions, and just listen. Not the kind of listening where you're preparing your response, but actual listening. The kind that makes the other person feel heard.
That next call with her morphed into what turned out to be his most productive of the month. The prospect spelled out exactly what she needed, why it mattered, and how she’d measure success. It wasn’t magic. It was patience.
Speed feels productive. But speed without connection just moves you past the point where trust could’ve been built. Here’s an example:
"Please Tell Me This Isn't Your Team..."
Our VP of Operations recently sat through a discovery call that, quite frankly, was painful.
The rep showed up in a wrinkled t-shirt. His tech partner was 8 minutes late and looked like he just realized what day it was. They kicked off with, “We’ve got some slides!” and rattled off their company’s greatness - headcount, awards, NPS scores.
What they didn’t do? Ask a single relevant question. Not one.
When our VP tried to steer the conversation toward the actual business challenges, the tech guy proudly pitched a “bucket of hours” and launched into a completely irrelevant service list. It was chaos disguised as a meeting.
Eventually, our VP politely ended it, thanked them, and moved on.
Curiosity Wins
You don’t have to overhaul your team’s playbook. But if you’re a leader, you can start asking your reps:
“What do you really know about the client’s world?”
“Are you solving a problem they actually care about?”
“Did you ask enough to earn the right to propose anything?”
“Where are they in the decision process?”
Strategic questions uncover truth. But only when asked with genuine curiosity, and enough stillness to wait for the answer. We have a process called SIGN for asking questions. It helps sellers uncover these answers and have the confidence and competence to solve the customer’s problems and win more deals.
But How Do You Slow Down...Without Falling Behind?
I hear this all the time: “We’d love to spend more time listening, but there’s just too much to do.”
That’s fair. Salespeople spend about 70% of their time on tasks that aren't selling: writing emails, digging up background, updating CRMs. So what gives?
That’s where AI steps in - not to replace people, but to give them space to do what matters the most
Let Tech Handle the Busy Work
Our clients use tools like our Sales Coach AI to reclaim their time. One team shared that background research dropped from 45 minutes to 3. Another said email drafting time fell by 75%. Prep for meetings? Down 82%. Ramp-up for new reps? Cut in half.
What does that mean?
It means your team has time to actually prepare thoughtful questions. To be fully present. To ditch the robotic multitasking and become real problem-solvers again.
With AI tools like Otter, Fathom, and ChatGPT’s meeting recorder, your reps don’t need to furiously take notes or try to remember everything. These tools catch the details. Your team catches the relationship.
And the results in win ratio and year over year growth are defying gravity. Their sellers are achieving 10x the results.
Technology for Transactions, People for Relationships
That’s something we teach and live by. Technology isn’t the star of the show, it’s the stagehand that sets your team up for powerful, human conversations.
In our training sessions, we don’t just tell you how to use AI, we role-practice real scenarios with your customer personas, objections, and strategies. Because it’s not theory that wins deals. It’s readiness, confidence and competence together.
Pass This On
If you’re a sales leader, share this with your team:
Real connection takes time. Make room for it.
Prepare to ask great questions. Not many - just the right ones.
Use AI technology to do the work that’s keeping you from people.
