There is a strange thing that happens when people become responsible for other people: they start feeling as though they’re supposed to know more than they do.
It makes sense. We promote people because they have experience. Founders are expected to have conviction. Executives are paid to make decisions. When something goes sideways, nobody calls a meeting because they want to watch the person in charge shrug and say, “I have no idea.” Leadership comes with an expectation of answers, and over time that expectation can turn into a habit. We get very good at answering quickly, defending what we already know, and moving everybody toward a decision.
The problem is that speed and certainty aren’t the same thing as good judgment.
A lot of expensive business mistakes begin with an answer that arrived too early. We assume the customer left because of price. We assume the employee isn’t performing because they don’t care. We assume sales are down because marketing isn’t working. We assume a competitor is winning because they have a better product. Once the explanation feels plausible enough, the organization starts moving around it. Meetings happen. Budgets change. People get hired or fired. New software gets purchased. Sometimes the original assumption was right. Sometimes we just built an impressive response to a problem we never actually had.
That distinction matters even more now because answers have become extraordinarily cheap. AI can give you ten strategies before you’ve finished your coffee. It can summarize the meeting, analyze the spreadsheet, draft the plan, challenge the plan, and produce another version when you don’t like the first one. The bottleneck is increasingly not access to an answer. It’s knowing whether you’re asking a useful question in the first place.
Curiosity, in that environment, starts looking less like a personality quirk and more like management infrastructure.
And apparently a lot of workplaces could use more of it. SurveyMonkey’s 2026 State of Curiosity research found that while 95% of surveyed workers described themselves as at least somewhat curious, only 30% said their workplace strongly rewards curiosity. Their research points toward a pretty uncomfortable possibility: companies may employ plenty of curious people while creating systems that quietly train the curiosity out of them.
That tension is what made my recent conversation with Jon Beebe on Eggs! The Podcast interesting. Jon calls his approach “curiosity-driven leadership,” built around a progression from curiosity to connection to community. jon-ryan What caught my attention wasn’t the framework itself so much as what sits underneath it: the idea that leadership improves when we become a little less interested in immediately proving what we know.
From Answers to Investigation
Jon Beebe spent fourteen years in ministry before moving full-time into entrepreneurship and the businesses he runs with his wife, Lauren. Along the way, he discovered that what he had initially understood as pastoral work was also leadership work: recruiting people, building teams, creating systems, developing volunteers, and building communities people actually wanted to remain part of.
Today, he brings that experience into his work around curiosity-driven leadership while continuing to operate Beebe’s Bargains, the family business that grew from Lauren’s deal-finding hobby into a staffed operation focused on helping families save time and money. Jon’s own company history describes the business as beginning with a Facebook group in 2018 before developing into a full-time operation.
What makes his perspective useful here is that he treats curiosity as something you do, particularly when your first instinct is to react.
Three Questions Worth Carrying Into Work
Jon's framework gets especially useful when it moves out of theory and into ordinary management situations. Three ideas from our conversation stood out.
1. Stop writing the story before you’ve reported it.
“Don’t tell yourself a story in your head about they’re saying this because they think this, this, and this... be a journalist. Really investigate.”
There may not be a more common management error than confusing an interpretation with a fact.
Someone misses a deadline and we decide they’re disengaged. A customer goes quiet and we decide the deal is dead. An employee pushes back and we decide they have an attitude problem. Pretty soon we’re responding not to what happened, but to the little screenplay we’ve written about why it happened.
Actionable insight: Jon’s journalist-versus-fiction-writer distinction is useful because it gives the leader another job: investigate before interpreting. What happened? What am I missing? What does the other person know that I don’t?
You may arrive at exactly the same conclusion. The difference is that you’ve earned it.
2. Better questions can change the size of the solution.
“The better question you ask will get you a better answer or get you a different answer.”
Jon uses a simple example in the conversation. If your car keeps breaking down, you can ask how you’re going to pay to repair it. That’s a perfectly reasonable question, and answering it solves the immediate problem. But you could also ask how you’re going to afford a different car.
Same breakdown. Different question. Different range of possible answers.
Actionable insight: Businesses do this constantly. “How do we get more leads?” produces one category of work. “Why aren’t more of the right customers choosing us?” produces another. “Who should we hire?” is different from “Why does this job require another person at all?”
Before putting more effort into an answer, it may be worth examining the question that’s generating it.
3. Put the leadership problem back on the leader first.
“We need to say, ‘I haven’t led them to do it yet.’”
I like this one because it’s uncomfortable.
Jon’s point isn’t that every performance problem is secretly the manager’s fault. Some people are wrong for a role. Some won’t do the work. Some eventually need to leave.
But “they won’t do it” closes the investigation. “I haven’t led them to do it yet” keeps it open a little longer.
Actionable insight: Maybe the expectation wasn’t clear. Maybe the person needs a different kind of instruction. Maybe they’re excellent but sitting in the wrong seat. Maybe the system around them makes success unnecessarily difficult. Or maybe, after looking carefully, you discover that they really aren’t right for the job.
The value is not avoiding accountability. It’s making sure the leader participates in it.
Certainty Is Useful.
So Is Knowing When to Distrust It.
Leadership still requires decisions. Eventually somebody has to stop asking questions and choose a direction. Curiosity without action can become its own kind of avoidance, and businesses don’t get very far if every decision remains permanently open for discussion.
But I suspect most organizations have the opposite problem.
We reward decisiveness because it’s visible. The person who speaks confidently in the meeting looks like they’re leading. The person who says, “I’m not sure that’s actually the problem” can look like they’re slowing everybody down. Under enough pressure, the incentive becomes obvious: answer first, investigate later.
That’s dangerous when technology can now manufacture convincing answers almost instantly.
The advantage may increasingly belong to leaders who know where to insert friction: one more question before the strategy, one more conversation before the judgment, one more attempt to separate what happened from the story we’ve attached to it.
The goal isn’t to become less decisive. It’s to become harder to fool—including by ourselves.
Thanks for reading.
—Ryan
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The Bezos Letters — Steve Anderson and Karen Anderson
Jon mentions Steve Anderson and The Bezos Letters during the conversation while discussing the difference between improving what already exists and creating something genuinely different. The book draws lessons from Jeff Bezos’s shareholder letters and organizes them around testing, building, accelerating, and scaling—making it a useful companion to this week’s argument about curiosity, experimentation, and the questions that precede growth.
Listen In/More to Explore
Eggs! The Podcast — Episode 483
Curiosity-Driven Leadership with Jon BeebeFollow Jon’s work
Jon Beebe on LinkedIn
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Eggs! The Podcast - https://www.eggscast.com
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