September offers a rare pause in the business calendar. The urgency of the first half of the year has eased, and the intensity of Q4 hasn’t yet taken hold. It’s a natural time to step back and examine our habits instead of simply measuring our activity.
One observation has stayed with me all summer. It was the closing thought in both conference keynotes I delivered this year, and the more I reflect on it, the more convinced I become that it explains why some experienced account managers continue to grow while others plateau.
“The most experienced people in the room have quietly stopped asking questions.”
Not because they don’t care. Not because they lack capability. They stop because experience convinces them they’ve seen this situation before. That confidence feels like expertise, and often it is. But sometimes expertise quietly becomes certainty, and certainty leaves very little room for curiosity.
I believe there are four lessons every account manager and sales leader should consider.
1. Experience Replaces Questions with Assumptions.
Experience gives us one of our greatest professional advantages: pattern recognition. We begin anticipating customer concerns, recognizing familiar situations, and seeing opportunities others miss. Those instincts are earned through years of hard work and are one of the reasons experienced professionals create so much value.
The problem is that those same instincts create what I think of as The Knowing Trap. The Knowing Trap is the moment experience quietly convinces us we’ve already understood the customer before they’ve finished telling us their story. We stop discovering and start confirming. Every experienced account manager has finished a customer’s sentence before the customer has actually finished speaking. We’ve all done it. Sometimes we’re even right. The danger isn’t being wrong. It’s being right often enough that we stop checking.
Every customer, every leadership team, and every quarter brings something different. Buyers know when someone is genuinely trying to understand their business and when someone is simply matching them to a familiar pattern. One approach builds trust. The other limits it.
2. Real Confidence Creates More Curiosity, Not Less.
Dan Sullivan reminds us that confidence comes after Commitment, Courage, and Capability. Genuine confidence is earned. That’s why truly confident professionals are often the most curious. They don’t need to prove they’re the smartest person in the room because they trust their ability to learn something they don’t yet know.
When confidence becomes certainty, curiosity begins to disappear. When confidence creates security, curiosity flourishes. That’s an important distinction because growth doesn’t stop when people lose capability. It often stops when they stop believing there’s anything left to discover.
3. Great Questions Create Better Customer Conversations.
Dan Sullivan and Dr. Benjamin Hardy make an important observation in The Gap and The Gain. When we constantly measure ourselves against an ever-moving ideal, we naturally feel behind, even when we’re succeeding. People who feel behind tend to become defensive, and defensive people make statements instead of asking questions.
The best customer conversations happen when people feel secure enough to remain curious. Buyers rarely remember your smartest answer. They remember the question that helped them see their own business differently. Great questions uncover opportunities, challenge assumptions, and deepen relationships in ways that polished presentations rarely accomplish. Trusted advisors aren’t remembered because they always had the answers. They’re remembered because they consistently asked the questions that mattered most.
4. Curiosity Is a Discipline.
Many people think curiosity is simply part of someone’s personality. I don’t believe that’s true. I believe curiosity is a professional discipline that can be strengthened through deliberate practice.
The best account managers don’t rely on inspiration. They build habits that force discovery before recommendation. Before every important meeting, they assume there’s a challenge they haven’t uncovered, a priority they haven’t heard, or an opportunity they haven’t recognized. In our own work, we’ve embedded that discipline into a structured questioning process that begins with strategic context, explores the customer’s business challenges, connects those challenges to strategic priorities, and only then considers possible recommendations. The sequence matters because it protects curiosity from being replaced by assumption.
The Master’s Mindset.
When I step back, I think there’s a simple progression that explains what happens to many successful professionals.
Beginners ask questions because they have to. Competent professionals solve problems because they’ve learned enough to recognize them. Experts trust their experience because it has served them well.
Then Masters become beginners again. The highest level of expertise isn’t having all the answers. It’s refusing to believe you’ve already heard them.
Stay a Beginner on Purpose.
Markets evolve. Customers evolve. Leadership teams evolve. Every quarter introduces new challenges that yesterday’s experience can illuminate but never completely explain. The moment we assume we already understand today’s challenge because we understood yesterday’s is the moment our growth begins to slow.
That’s why the Knowing Trap is so dangerous. It doesn’t happen to inexperienced people. It happens to experts. The more successful we become, the easier it is to believe we’ve already seen this movie before. The best account managers recognize the trap and deliberately avoid it. They never lose their expertise. They simply refuse to let expertise become certainty.
The next time you walk into a customer meeting, assume you’re wrong about one important thing. You don’t know what it is yet. That’s exactly why you need to ask. In the end, curiosity isn’t the opposite of experience. It’s what keeps experience valuable.
A Question for Leaders.
If you’re leading a sales or account management team, ask yourself one question:
“Are your people bringing customers answers, or are they helping customers discover better questions?”
The difference is often the difference between becoming a trusted advisor and remaining just another supplier. Helping organizations build that capability has become the focus of my research, keynote presentations, executive workshops, and advisory work.
If this article sparked a new way of thinking, I invite you to continue the conversation. If your sales results have fallen short, now is the time to upskill your people. Turnaround takes time. Don’t wait until the end of the year. If your organization is looking to strengthen customer conversations, align sales and account management around a common questioning discipline, or build deeper client relationships, I’d welcome the opportunity to talk.
