The Grocery Store, the Cornfield, and the Stories That Shaped Future Leaders
- 22 hours ago
- 6 min read
By Dr. Rod Berger | Storyteller in Residence | CultureCon
There's a question I ask nearly every leader I sit down with, and it never arrives the same way twice.
Sometimes it sneaks in between career milestones.
Sometimes it lands in the middle of a medical scare or a divorce filing.
The question is simple: When did you stop telling someone else's story and start telling your own?
I asked some version of that question twice today, once to a man who learned leadership behind a grocery store checkout counter in Maine, and once to a culture officer in Iowa who nearly bled to death on a high school baseball field.
Their answers were completely different.
Their lessons couldn't have been more alike.
Leadership Origin Story: The Hannaford School of Leadership
Matthew Caldwell didn't rise through an Ivy League school or a Big Four consulting firm. Instead, he came up through Hannaford, the grocery chain, where he spent over thirteen years stocking shelves, managing staff, and learning leadership that doesn't need a fancy title.
“I went to Hannaford School,” he told me, laughing, “and that's how I got to where I am.”
Today, Caldwell serves as the Director of Organizational Development for the Maine Secretary of State's office, overseeing the Bureau of Motor Vehicles and the Office of Human Resources. He assists Maine, the second-oldest state in America by median age, in figuring out how to attract, retain, and develop a workforce when most traditional strategies weren't designed for the demographics he's managing. Maine recently became only the second state recognized as a certified age-friendly employer, and Caldwell's influence is evident in that achievement.
But the story behind his leadership isn't just about policy. It's about a time of personal reflection that most leaders would never openly share, and I believe that's exactly why it matters.
In 2019, Caldwell went through a divorce and came out as gay to his friends, family, and colleagues. He told his kids. He started therapy that lasted a year and a half. And something remarkable happened: the vulnerability that nearly broke him became the foundation of his leadership.
"I had to go through the darkest point in my life," he said, with the kind of steadiness that only comes from having actually walked through it. The experience didn't just change how he saw himself; it changed how he showed up for the people he leads.
It gave him what I refer to in my work as a permission structure, the ability to create spaces where others feel safe enough to bring their full selves to the table, not just the parts that fit neatly into an org chart.
I've spoken before at CultureCon about permission structures and the invisible barriers that decide whose stories are shared within organizations. Caldwell proves that these barriers aren't only in corner offices and conference rooms. They reside within us, and breaking them down is an inside job.
Leadership Origin Story: The Culture Farmer
Todd Wuestenberg has worked at the same company for twenty-one years. He's the Chief Culture Officer at Haverkamp Group, and if you're expecting a polished corporate story about climbing ladders, you'll be disappointed. His story starts in a small Iowa town of 1,500 people, graduating in a high school class of forty-eight, and watching his father model something over coffee every morning that no leadership seminar could teach: the patience to listen before you speak.
The story that defines Todd's approach to leadership happened on May 23, 1986, on a baseball field. A collision during a play ruptured his spleen so catastrophically that the surgeon told him afterward the organ had shattered into pieces across his abdomen.
He was seventeen.
The doctor told him, "Do not play the lottery. You used your one in a million."
That near-death experience at seventeen planted something. But it took a second medical event, thirty-five years later, to bring it to full harvest. In July 2021, on the very same day Todd was passed over for a VP promotion he'd been working toward, he received a call from an oncologist about a condition called splenosis, remnants of that shattered spleen from 1986, now appearing on scans in a way that mimicked something far worse.
There are some things more important than a title," he told me, with the clarity that only comes when the body reminds you that the scoreboard isn't where you think it is.
Todd calls himself a "culture farmer." It's not a brand exercise; it's an identity rooted in the Iowa soil he grew up on. He talks about organizational culture the way a farmer talks about a growing season: you can't rush it, you can't fake it, and if you stop tending to it, the second law of thermodynamics takes over.
Things regress.
Todd borrows from Edgar Schein, the organizational culture researcher, when he says culture is a matter of organizational life and death. But he grounds it in something more personal:
"Culture is never neutral."
That line deserves to sit with you for a moment. Because it means every decision, every silence, every meeting that runs over, every recognition that doesn't happen, is a cultural act. Todd doesn't own the culture at Haverkamp Group. He stewards it. And there's a world of difference between those two verbs.
Two Leaders, One Throughline
I keep returning to the same point as I reflect on numerous interviews with leaders worldwide: the leaders who influence culture most profoundly are those who have done the toughest internal work on their own stories first.
Not the polished keynote version.
The version that includes the grocery store and the divorce papers. The ruptured spleen and the promotion that didn't happen.
In my previous CultureCon articles, I've discussed why the best culture leaders prefer playing board games over chess, creating spaces where people can experiment with their narratives without the fear of being checkmated. I've addressed the listening deficit that affects leaders who confuse broadcasting with genuine communication.
Caldwell and Wuestenberg exemplify these points, proving that organizational storytelling doesn't start with a communications strategy. It begins with the willingness to excavate your own story, the parts you inherited, the parts you chose, and the parts you're still writing.
This is what I mean by narrative discernment: the ability to identify which stories serve you and which ones you're repeating out of habit or obligation. It's the difference between a leader who recites values from a laminated card and one who can share the exact moment those values became real to them, whether in a hospital room, on a therapy couch, or over coffee with a father who believed conversation was the highest form of currency.
The Invitation
Matt and Todd reinforced the bedrock principle of one’s origin story: your story is not a liability.
It's not a distraction from the "real work" of leadership.
It is the work.
The origin stories we carry from checkout lines and cornfields, from personal reckonings and medical scares, aren't footnotes to our professional lives. They're the text.
The organizations that will succeed aren't necessarily the ones with the most polished culture decks. They are the ones brave enough to let their people show up as whole human beings, with all their messy origin stories. Caldwell navigates Maine’s state offices, building relationships one conversation at a time. Wuestenberg tends to his organizational culture as if it were a crop that needs daily care.
Neither of them learned that from a textbook.
They learned it the way all of us do: by living a story worth telling and then having the courage to share it.
The question for every culture leader reading this isn't whether you have a leadership origin story.
You do.
The real question is whether you've allowed yourself and your team to tell it.
Be on the lookout for my Narrative Edge podcasts with Matt and Todd in the coming weeks.
Dr. Rod Berger is the Storyteller in Residence for CultureCon and the author of The Narrative Edge: Authentic Storytelling That Meets The Moment (Wiley). His companion Field Guide, coming out in the fall of 2026, provides exercises for leaders ready to excavate, develop, and activate their stories. To bring storytelling workshops or keynotes to your organization, reach him at rod@drrodberger.com.
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