The Natural: One Leader’s Rise from the Closing Table to the Head of the Table. 

Ask Lisa DeWolf if she ever dreamed of being President of an organization like Trident Land Transfer, and you’ll get a quick, decisive “no.” For years, she passed on leadership titles, but never on the chance to deliver superior service to her clients and colleagues at the closing table. Perfectly content to be the undisputed champ in her role as a settlement officer, she thought she could stay there forever.  She loved the job, including the energy of the closing table, the chance to walk first-time homebuyers through the most important purchase of their lives. “I always loved interacting with buyers and sellers,” she recalls. “Particularly first-time homebuyers. That energy is contagious.”

But when leadership opportunities came, she recoiled. Her first taste of management had been under a mentor who drained more than she gave, someone whose gray outlook snuffed out her optimism. She wanted nothing to do with that version of leadership.

So when she joined Trident in 1998, her mission was simple: do great work and avoid management at all costs. But her boss, the legendary Barb Griest, saw what she couldn’t deny forever: a natural leader hiding in plain sight. Griest asked her three times to step into management, and she refused twice. On the third ask, she relented, reluctantly opening the door to a new chapter.

A Trial by Fire

That door swung wide in 2010. The housing crash had gutted the market, and instead of retreating, Trident’s leadership doubled down on the future. They hand-picked seven employees for an intensive year-long leadership program. The assignment: design the “Office of the Future.”

For DeWolf, it was a trial by fire. She juggled her day job with late nights full of case studies, interviews, and business books. “I felt insecure. I felt like I didn’t belong in the room with the other people,” she admits. The pressure was immense, and she leaned heavily on her mentor, convinced she might fail.

But she didn’t. She stuck with it, driven by a simple thought: Where else am I going to get this education? By the end, the team produced a vision for the then Prudential Fox & Roach, and the Trident Group's future and delivered it directly to the company’s owners. The project didn’t just sharpen her skills. It forged her confidence. For the first time, she realized she wasn’t just capable of sitting at the table. She belonged at the head of it.

Born, Then Made

Ask DeWolf today if leaders are born or made, and she won’t hesitate. “I think that I’m born a leader,” she says. “Even when I tried to run away from it, there’s just something in me that takes charge, that stands up… I can’t sit quietly.”

But she also knows that raw talent alone isn’t enough. Leaders may be born with a spark, but that spark has to be shaped. For her, the “Office of the Future” project was the forge, and mentors like Barb Geist were the hammer. A company psychologist later captured it perfectly, telling DeWolf she had the rare ability to see the world from both the trenches and the 30,000-foot view.

Her leadership was both natural and made. Instinct sharpened by pressure, talent refined by trial.

Leading Through Resistance

Her next assignment tested every bit of that growth. DeWolf was tasked with leading a large department of seasoned industry veterans into the digital era. For people who had spent 15 or 20 years working in paper, the resistance was fierce.

“They didn’t want to hear from me,” she recalls. “I was the last person they wanted leading this change.” But instead of bulldozing through, she invited them in. She gave them space to poke holes, to question, to object. Her team listened, adjusted, came back with answers, and repeated the process until every objection had been addressed.

Once the arguments were gone, her message was clear: This ship is moving forward. You can get on board, or you can find another port.

The transformation was real. One of her harshest critics, someone who openly resisted her leadership, eventually became her biggest supporter. Years later, when that woman passed away, DeWolf introduced herself to her husband at the funeral. His words stunned her: “She loved you.” For DeWolf, it was the kind of validation no title or promotion could ever top.

The Inevitable Leader

Today, Lisa DeWolf is no longer running from leadership; she’s redefining it. The same passion she once poured into guiding first-time buyers now scales across an entire organization. The lessons of her reluctant yes and her trial by fire continue to shape the way she leads: with ground-level empathy, big-picture vision, and a voice that won’t sit quiet.

The “Office of the Future” project wasn’t just a leadership exercise,  it became her playbook. It taught her to challenge the status quo, to anticipate what the next generation will need, and to weave her own natural instincts into a leadership style that feels both authentic and forward-looking.

Lisa DeWolf’s story is a reminder that some leaders rise by choice, but the most compelling ones rise because they can’t help it. For her, leadership wasn’t a destination she sought; it was a calling she could no longer outrun. She is, simply, the natural.