From Carpool to the C-Suite: Redefining Leadership (and Motherhood) on Her Own Terms

When Amy Henson stepped into the role of VP of Operations at ARC Realty, she didn’t just inherit a title—she inherited expectations, an evolving company, and a new way of seeing herself.

In this episode, I sat down with Amy to talk about what it's really like to lead when you’re still defining what that leadership looks like. We talked about:

* Taking over after someone beloved leaves

* Growing from task-driven to people-driven work

* The mental shift from managing a home to managing a company

* Learning to set boundaries as a working mom and executive

* And yes, we even talked about sending calendar invites for date nights with our husbands (non-negotiable).

Stepping Into the Unknown

When Amy took over the VP of Operations role, it wasn’t a simple baton pass. It came with growing pains, steep learning curves, and the humbling reality of needing to bet on herself before she fully believed in her own capability.

“I deleted Paige’s email from my inbox this week,” Amy told me. “It felt like a moment. Like, ‘Okay, I don’t need to ask her about everything anymore. I’ve got this.’”

From office relocations to staffing transitions, Amy found herself not just learning on the job, but learning how to define a job that hadn’t fully existed in its current form before.

Redefining What “Work” Looks Like

As someone who had been at home for years, Amy was no stranger to hard work—but work in a professional setting brought new challenges. “You go from being task-oriented to people-oriented. And that’s a totally different kind of effort.”

She’s the first to admit she didn’t go to school to run operations. But she’s found herself in the thick of it—overseeing teams, connecting systems, problem-solving when the HVAC goes out or water appears on the office floor.

And along the way, she’s realized the skills honed at home—time management, multitasking, communication—are some of the most transferable and powerful tools in her toolbox.

Boundaries, Guilt, and Growth

Amy and I both laughed (and nodded seriously) at the idea of “leadership guilt.” That lingering pressure to always be present, always available, always proving our worth. And yet, we know—especially as women—that boundaries are essential.

Amy shared how leaving her laptop at the office was a game-changer. “I’m still working on it, but it’s helped me compartmentalize. When I’m home, I want to be present.”

That intentionality doesn’t stop with work hours. It extends into date nights with her husband (yep, scheduled on the Skylight calendar) and showing her kids—especially her daughter—what it looks like to step into leadership with humility and strength.

Lessons from the Home Front

Amy’s youngest once joined her for a day at work and came home saying, “Whew, that’s a long day. And then you have to deal with us.” That tiny moment? A big reminder that kids are watching, learning, absorbing more than we realize.

“I want her to see that you don’t have to have it all figured out at 18,” Amy said. “You can evolve. You can change. You can do something completely new at 43.”

Operations as Art

The work Amy does may not always be easy to define, but it’s deeply felt. She’s helped shape the structure that lets 950 agents function like small businesses—smoothing the friction between departments, building communication across teams, and fostering a culture where people are empowered to act without waiting for approval.

“Right people in the right seats with just a little direction can do incredible things,” she said. And that’s exactly what’s happening under her leadership.

What Amy’s Still Working On

* Saying no without guilt

* Taking Fridays off without explanation

* Letting go of the idea that leadership means being tied to a desk

* Learning to be okay with being a work-in-progress

She’s a self-proclaimed terrible note-taker and a reluctant goal-setter. But when she sets her mind to something? She gets it done. Just ask her about passing her real estate exam—at 11 PM the night before her deadline.

So what’s next for Amy?

More clarity, more alignment, and more open communication with her team. “I want to know what success looks like—because once I know that, I can build toward it.”

From carpool to the C-suite, Amy’s not just running operations. She’s rewriting what modern leadership looks like—for herself, her family, and the next wave of women stepping into more.

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