Sales conversations break down when we rush to fill in the blanks.
Whether you’re a Managing Partner or a CRO, your team’s most dangerous habit probably isn’t a lack of CRM adoption or even poor qualification. It’s assumptions. Assumptions about what the buyer meant. About how the conversation is going. About what that vague “we’re already working with someone” really signals. And when your team fills in the blanks with their own internal stories instead of facts from the client? Deals slow down. Trust erodes. Margins shrink.
In our most recent Sales Foundations class, we tackled what it means to be curious and how to stay in control of high-stakes conversations without getting reactive or defensive.
Most Salespeople Jump in Too Fast.
When a client says, “Your fees are higher than others,” the average salesperson scrambles to defend value. The smart ones pause. They ask a follow-up like, “When you say higher, help me understand, compared to what?”
This doesn’t just shift the tone. It shifts the power.
Salespeople who master the art of reversing, using questions to redirect and clarify, are better positioned to learn what’s going on behind the objection. Are we dealing with sticker shock? A false comparison? Or are we talking to someone who’s never had to defend the budget internally and is now using price as a smokescreen?
Senior executives, if you expect your teams to win complex deals, they need to learn how to sit in that tension. Silence is not a gap to fill. It’s a lever.
Curiosity Is a Discipline, Not a Personality Trait
We like to believe our people are “naturally curious.” But curiosity in sales is being disciplined enough not to assume we know what the buyer means until we ask a clarifying question. That second or third question is where all the value is hiding.
One of our favorite lines to practice in class:
“If there’s one thing your current firm could do better, what would it be?”
It’s a deceptively simple question. But it opens the door to dissatisfaction, urgency, and unmet expectations, without attacking the incumbent or pushing an agenda.
The best salespeople don’t aim to replace a vendor. They aim to uncover what’s missing.
Your Team Might Be Reacting When They Think They’re Responding
Here’s what we see over and over in live role-plays and real-world debriefs: someone hears a pricing objection or a dismissive comment like “We’re just exploring options,” and the response gets subtly defensive. Even seasoned professionals fall into this trap.
The antidote is preparation and presence. We teach people to identify these pattern triggers early, so instead of defending or convincing, they can flip the frame. For example:
Prospect: “We’re just exploring options.”
Your rep: “Thanks for saying that. Would it make sense to share a bit about how we work with firms like yours, and then you can decide if it makes sense to continue the conversation?”
This is delivered calmly and without pressure, rooted in mutual respect.
Executive-Level Conversations Require an Executive-Level Mindset
In Foundations, we don’t just teach techniques; we reshape default mindsets.
When someone accuses you of not listening, what do you do? If the answer is anything other than “slow down and ask a follow-up,” you’re signaling defensiveness. Buyers can sense it, even when it's subtle.
Your team’s ability to navigate difficult conversations without shifting into explanation mode is what earns them equal business stature. That means being OK with hearing “no.” It means not rushing to solutions. It means listening harder when things get tense.
If your team can master this, you’ll see more honest conversations, faster no’s and yeses, and more high-quality deals.
Leadership Takeaway
If your team isn’t regularly practicing how to ask the second question, how to control silence, and how to stay neutral when the buyer’s guard goes up, they’re leaving money on the table.
The truth is, your people don’t rise to the occasion. They fall back on their training.
Want to help your team build real conversational control without losing their authenticity?
You know where to find us.
Megan Courcy is Vice President at Next Level, a top-performing Sandler training firm serving senior leaders across professional services and complex B2B industries. She helps executives create sales cultures that change the way your people think and sell.
