Date: March 13, 2025
Location: Industrious U District, Seattle
Presented by: Kalles Group, Industrious, Treat Cookies
Facilitated by: Bryon Scharenberg, Director of Growth at Kalles Group
Bringing Leaders Together to Talk About Change
Change is constant—but navigating it well? That takes skill, courage, and clarity.
That’s exactly what we explored at our most recent Smart Cookies event. I had the privilege of hosting the evening and guiding a conversation with three incredible leaders, each bringing hard-earned wisdom from high-stakes roles.
Over 60 attendees joined us at Industrious in the University District, and the energy in the room reminded me just how valuable it is to learn from real people doing real work. I’m so grateful to our panelists—not just for their insights, but for their honesty, humility, and humor. Because let’s be real: when you’re talking about leading through complex change, a little humanity goes a long way.
Meet the Panelists
Anthony Kappus – Chief of Legal Affairs & Digital Revenue, Redfin
Anthony offered a behind-the-scenes look at Redfin’s journey—from IPO to its recent $2.4B acquisition by Rocket Mortgage. What stood out was his unique ability to bridge legal strategy and business growth, especially in high-stakes, high-ambiguity environments. Anthony brought a blend of humor, honesty, and real-talk to the panel, sharing candid reflections on the ups and downs of leadership and how embracing uncertainty has helped him grow with confidence and clarity.
Vanessa Pegueros – Corporate Board Member & Technology Executive
Vanessa shared grounded, insightful lessons from her time leading transformation at companies like DocuSign and Expedia, and from her board work with organizations like BECU, LivePerson, and Presidio. She spoke candidly about navigating risk and uncertainty—and reminded us that leadership doesn’t require having all the answers. Instead, it’s about being clear on your principles, decisive in your action, and confident in who you are as a leader. You don’t have to lead like everyone else—you just have to lead like you.
Jon Duarte – President & CEO, Overlake Medical Center & Clinics
Jon brought a grounded, deeply human perspective to the conversation. Whether navigating the complexities of Overlake’s merger with MultiCare or scrubbing into surgeries to better understand the daily realities of his teams, Jon exemplifies servant leadership in action. His curiosity, humility, and commitment to learning from those around him reflect a leader who puts people first—at every level of the organization.
Key Leadership Insights from the Panel
- Change is a people issue before it’s a strategy issue.
We often think of change in terms of org charts or business plans, but the real work is human. Jon spoke to aligning people from the boardroom to the bedside. Vanessa reminded us that “change isn’t just hard—it’s personal.” And Anthony emphasized that tough decisions often come with personal cost—but doing what’s right, even when it’s hard, is ultimately what serves people best in the long run. Clarity, conviction, and care go hand-in-hand. - When uncertainty is the only constant, clarity becomes a superpower.
Whether driving a major acquisition or mitigating cybersecurity risks, each panelist spoke about learning to lead without perfect information. Anthony shared how moving forward—rather than waiting for certainty—has become one of his greatest leadership strengths. Vanessa echoed the importance of decisiveness, even when the path isn’t entirely clear. And Jon emphasized that admitting you don’t have the answer can actually empower your team to find the way forward together. - You don’t need to be perfect to be a great leader.
Mistakes, pivots, pressure—every panelist had a story. What stood out to me was Vanessa’s take on imposter syndrome: she’s never experienced it. Instead, she leads from a deep confidence in who she is—her unique strengths and even her limitations. It surprised many in the room, but it was a powerful reminder that leadership doesn’t come from fitting a mold. It comes from knowing yourself. And when leaders embrace their identity—fully and honestly—they’re able to lead with clarity, conviction, and courage. - Your leadership is shaped by your values.
Jon’s story about stepping into scrubs wasn’t just symbolic—it was leadership through empathy. Anthony’s shift from legal to revenue showed the power of stretching beyond your comfort zone. Each of them reminded us that leadership isn’t just what you do—it’s how you show up.
One Final Thought
As we wrapped the night, I asked each panelist:
“What’s one leadership cliché you think people get wrong?”
The answers?
Jon challenged the familiar advice: “Do the job you want to have.” His take? That mindset can pull your focus away from doing great work in the role you’re in now. Excellence in the present—showing up fully where you are—is what opens doors, not daydreaming about the next rung on the ladder.
Vanessa pointed to the problem with leadership books that prescribe how to lead. “Everyone is different,” she said. The best leaders develop their own authentic style—and not every organization needs the same kind of leader. “You need to find where your leadership style fits.”
Anthony added that leadership isn’t about cobbling together an idealized set of traits to become some kind of “perfect” leader. That Frankenstein approach doesn’t work. Instead, “You have to understand who you are, where you’re strong, and where you’ll thrive.”
What I Took Away
Confidence in leadership doesn’t come from pretending to be someone else. It comes from knowing who you are—and who you’re not. What struck me as I listened to each panelist was how clearly they’ve come to understand that. They were real, grounded, and humble. And maybe the most powerful takeaway of all? Telling the truth about what you don’t know is often the best kind of leadership there is.
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