The Curious Leader's Advantage
Why the best insights come from the strangest places
In 1997, physicist Sidney Nagel noticed something odd about his morning coffee. When a drop dried on his desk, it left a dark ring around the edge instead of an even stain. No one had asked him to solve this mystery. It wasn’t going to land him a research grant or change the world. But Nagel couldn’t let it go.
He spent months studying the physics of drying droplets. What he discovered—that particles migrate to the edges as liquid evaporates—revolutionized everything from inkjet printing to medical diagnostics. A curious mind chasing a mundane question unlocked breakthrough applications across multiple industries.
I think about Nagel often in my role leading a K12 sales organization. Not because I’m secretly a physics enthusiast, but because the best insights I’ve gained as a leader—the ones that actually changed how I coach, sell, and think—rarely came from sales books or industry conferences.
They came from a Kurt Vonnegut essay on storytelling. From watching how my daughter’s teacher handled a difficult parent at open house. From reading about jazz improvisation on a rainy Sunday. From a behavioral psychology study that sat open on my laptop for three weeks before the implications hit me.
The sales world celebrates confidence, decisiveness, and expertise. But I’ve become convinced that curiosity might be our most undervalued leadership skill.
The Confidence Trap
The higher you climb in sales leadership, the more people expect you to have answers. Clear directives. Proven playbooks. Definitive strategies.
That expectation becomes a trap.
Because while frameworks like MEDDPICC and methodologies like Challenger provide structure, they’re just containers. The real work—the stuff that actually moves deals and motivates teams—happens in the gray spaces between best practices.
Like the district that enthusiastically says yes, then goes completely silent for six weeks.
Or the rep who follows every process perfectly but somehow can’t close anything.
Or the customer who raves about your solutions, sends glowing testimonials, then quietly doesn’t renew.
There are no playbooks for these moments. No slides in your sales kickoff deck that explain why seemingly identical prospects behave completely differently. The leaders who navigate these situations best aren’t the ones with the most certifications—they’re the ones who stay curious about what they’re observing.
They notice patterns. They ask better questions. And crucially, they’re comfortable saying “I don’t know, but let’s figure it out together.”
Curiosity as Competitive Advantage
Watch a genuinely curious sales rep in action. They don’t just ask discovery questions—they ask follow-up questions to the follow-up questions. They lean forward when prospects talk about challenges that aren’t even related to their product. They remember details from conversations three months ago.
Prospects can feel the difference. Curiosity creates trust in ways that competence alone cannot.
The same dynamic applies to leadership. When you approach team challenges with genuine curiosity rather than immediate solutions, something shifts. Your one-on-ones become more honest. Your coaching becomes more relevant. Your team starts bringing you the real problems, not just the sanitized versions they think you want to hear.
Early in my leadership journey, I noticed something puzzling: some reps had perfect pipeline hygiene but consistently missed quota. Others were sloppy in Salesforce but landed massive, unexpected wins. I could have chalked this up to “different working styles” and moved on.
Instead, I got curious. I started asking different questions in our coaching sessions. Not just about process and pipeline, but about preparation rituals, confidence levels, and how they used storytelling in their conversations.
Those questions opened doors to discussions about motivation, anxiety, and personal mission—topics no sales training had ever addressed. Understanding these deeper dynamics didn’t just improve my coaching; it helped me identify what actually drove performance for each individual on my team.
Learning from Unlikely Teachers
I’m not an academic, but I’ve always been a promiscuous reader. History, psychology, fiction, science—anything that catches my attention. Over the years, I’ve found that the ideas that stick with me, the ones that genuinely change how I lead, rarely come from business books.
Kurt Vonnegut on Story Structure
Vonnegut wrote that every story needs a character who wants something desperately and faces obstacles to getting it. Simple advice for fiction writers—profound insight for sales conversations.
Most reps focus on features and benefits. But Vonnegut’s principle revealed something deeper: urgency doesn’t come from product capabilities. It comes from narrative tension. From helping buyers understand what’s truly at stake.
I started coaching my team on story arc, not just value propositions. “What does your buyer want most? What’s standing in their way? How does our solution help them overcome that obstacle?” This shift created more conviction in our messaging and more emotional resonance in our conversations.
Angela Duckworth on Grit
Duckworth’s research on grit—passion and perseverance toward long-term goals—completely changed how I interview candidates. I stopped asking where they saw themselves in five years and started asking about times they stuck with something difficult that didn’t pay off immediately.
Sales is fundamentally a delayed-gratification profession. You can teach someone to demo software or handle objections. But grit—the willingness to persist through rejection, to maintain optimism during long sales cycles, to keep improving after setbacks—that’s either there or it isn’t.
Fred Rogers and the Power of Presence
As a former educator who grew up watching Mr. Rogers, I always appreciated his gentle approach. But revisiting his work as a leader helped me see something I’d missed: beneath all that kindness was a masterclass in presence. Still. Focused. Radically empathetic.
That became the posture I try to adopt in one-on-ones. Not rushing to give advice or solve problems, but truly listening for the concern beneath the concern. I don’t always succeed, but this shift has made me a better coach and a more trusted leader.
Jazz and the Freedom of Structure
Jazz isn’t musical chaos—it’s freedom within form. There’s a standard, a chord progression, a time signature. Within those constraints, musicians respond to each other in real time, bending rules and creating something new.
That’s how I think about sales processes now. We need structure—talk tracks, battle cards, objection handling. But the best reps improvise. They listen closely and respond to what they hear. My job is to give them the framework and then trust them to make music within it.
Why This Matters Now
Curiosity isn’t just personal enrichment for leaders—it’s a practical necessity. The sales landscape changes too quickly for expertise alone to keep up. What worked last quarter might not work next quarter. The methodology that transformed your team two years ago might be exactly what’s holding them back today.
Curious leaders adapt faster. They notice shifts in buyer behavior before they become obvious trends. They identify team dynamics that others miss. They ask questions that reveal hidden obstacles and unexpected opportunities.
But there’s something deeper here too. In a profession that can feel mechanical—quotas, pipelines, forecasts—curiosity keeps the work alive. It reminds you that every prospect is solving a unique puzzle, every rep brings different strengths, every conversation holds potential for genuine insight.
That sense of discovery, of always learning something new, might be the best defense against leadership burnout.
The Practice of Purposeful Wandering
The leaders I most admire are collectors. They collect stories, concepts, questions, and unexpected connections. Then they find ways to apply those collections to the real work of motivating teams, closing deals, and navigating change.
This isn’t about being an intellectual or impressing people with random knowledge. It’s about staying alive to possibilities. About maintaining the beginner’s mind that sees patterns others miss.
Here’s what that looks like in practice:
Read outside your lane. Subscribe to something completely unrelated to sales. Psychology Today. The Atlantic. Scientific American. Anything that stretches your thinking.
Ask different questions. In your next one-on-one, skip the tactical review and ask about energy levels, confidence, or what they’re learning about themselves.
Share strange connections. When you discover an insight from an unexpected source, share it with your team. Ask them how it might apply to your work.
Embrace not knowing. The next time a team member brings you a problem, resist the urge to immediately solve it. Say “That’s interesting. What do you think is really going on here?” and explore it together.
Notice what you notice. Pay attention to patterns, anomalies, and your own reactions. What keeps surfacing in your conversations? What feels different this quarter compared to last?
Sidney Nagel could have ignored that coffee stain. It wasn’t his field, wasn’t his problem, wasn’t even particularly important. But he stayed curious. He followed the question wherever it led.
That’s what great sales leaders do every day. They notice things that others miss. They ask questions that reveal new possibilities. They stay curious about the work, the people, and the world around them.
In a field that rewards knowing, they remember the power of wondering.