You Lost The Deal Because You Lost Your Nerve

Welcome back to the 56th issue of Disrupting Conversations!

My team and I have spent a lot of time doing film studies: reviewing recorded sales conversations to understand the human behaviors that separate conversations that accelerate from those that stall.   

Nine times out of ten, we see the same thing happen: A sales professional poses a strong question, and the prospect responds with a shallow, surface-level answer. And instead of pressing further, the sales professional quickly calls an audible and switches topics entirely. 

No follow-up. No attempt to go deeper. They just move on to a different question, story, or feature—anything to ease the awkwardness they’re perceiving. 

Why does this happen so consistently? When you ask a meaningful question and receive a weak response, your brain immediately interprets it negatively. You start thinking: "They don't want to engage with me. I've overstepped. If I push any harder, I'll annoy them. If they get annoyed, they won't want to continue talking with me."

That internal monologue? That’s negative bias at work, and it’s what holds you back, stripping you of your courage to double down and trust yourself to re-craft the question. More importantly, it prevents the other person from transitioning from routine thinking to critical thinking. They never immerse themselves, avoiding becoming fully invested in the conversation. 

That’s a problem. Breaking that pattern starts with understanding what immersion looks like, what it can tell you, and how to cultivate it. Keep reading to discover the full framework. 

– Dan

P.S. In case you missed it, our podcast, Breaking Sales, has officially debuted on YouTube! Every conversation we’ve had about mindset, performance, and what it actually takes to sell is available on our channel, so if YouTube is where you like to listen to your podcasts, we’ve got you covered. Subscribe here, and turn on notifications so you never miss an episode.

Breaking Sales is my podcast to connect with those who are ready to break free from the chains of old sales methodologies that don’t work.

Title of Episode: Say Less To Get More: Embracing The Power Of Silence In Conversation

🎙️ There’s a tendency to treat silence in sales conversations like a problem that needs solving. The prospect pauses after your question, and immediately you're scrambling to fill that gap—explaining, clarifying, and trying to keep the conversation moving. When you do, you’re robbing your prospect of the space they need to actually think. 

In this episode, Pam Evanson and I break down why jumping in to fill every pause might be sabotaging the depth of insight you could be getting. We show you how to stop labeling every interaction as "good" or "bad," and what happens when you finally let go of the urge to control the narrative. If you’re serious about building immersion in your conversations, this episode will show you how to create the conditions for prospects to share what's truly on their minds.

When a prospect is actually invested in a conversation—when they’re willing to slow down, reflect, put real thought into their answers, and work through their assumptions and reasoning—that's immersion: the process of going from routine thinking to critical thinking.

Routine thinking is idle. It’s based on past experiences, lessons learned, current assumptions, and curated biases. 

Critical thinking, on the other hand, is reflective. It’s what allows us to challenge our past experiences, learned lessons, and current assumptions. When we think critically, we’re able to identify our biases and the impact they’re having on our decision-making.  

Think about it - if you want the other person to consider change, which kind of thinking are they going to have to engage?

The immersion process is powerful on two fronts: On the prospect side, immersion is your sign that they’re making a sincere evaluation, investing genuine effort into the conversation. When a prospect is immersed, they’re not just going through the motions of responding to your questions. They're actually in the game with you. And when you, as the sales professional, work to create that immersion, you're showing them you care about their thinking, not just your own pitch. That’s what builds trust and makes you more effective.

👉 But immersion doesn't happen automatically. Our brains naturally default to surface-level thinking. We rarely show up to conversations primed for deep reflection or critical analysis. Something has to prompt us to engage at that level. 

Many of the sales professionals I observe don’t understand this. They rarely push for that deeper thinking. They write off responses like silence, hesitation, or disengagement as “negative” and move on too soon—even in moments when they should be doubling down.

The thing to remember is that there are three main reasons why a prospect might resist going deeper with you: Either they don’t trust you or the intent of your questions, they’ve already made a decision to go in a different direction (one that doesn't involve you), or they haven't yet decided that they want—or need—to make a change. 

👉 When a prospect is struggling to objectively evaluate the risks and benefits of their options, to determine if committing time and effort to this decision makes sense, that's your opportunity—but you won’t know unless you lean in. 

So when you encounter resistance, slow down. Remind yourself that you owe this person meaningful questions that will help them better debate change—and that if you don’t ask those questions, you’re actually doing them a disservice. Remember, this isn’t about hearing the answers you want; it’s about getting to the truth. It’s also important to shape your questions with empathy and help them understand why their answers matter. 

This creates huge value for the prospect because it helps them do the critical thinking required to make a better, more informed, and more objective decision. And it creates value for you, too. 

When your efforts to help a prospect immerse themselves into a different level of thinking are ineffective, it’s confirmation that something fundamental is missing—whether trust or openness to your solution—that no amount of follow-up will change. By recognizing when this happens, you can stop wasting time chasing a deal that was likely never going to go through anyway. 

👉 The next time you ask a strong question and get a weak answer, don't let your negative bias win. Recognize it as an opportunity to lean in—because the depth of your prospect’s thinking tells you the depth of their commitment. 

And if they still won't go there with you? That's valuable information, too.

QUOTE

"Thinking is the hardest work there is, which is probably the reason so few engage in it." 

– Henry Ford

Thanks for reading!

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