What If With Leslie Grandy

What if the most powerful thing a leader can say right now is, "I don't know"?

In this episode of What If?, Leslie Grandy sits down with Hortense le Gentil, executive leadership coach, speaker, and author of Aligned and The Unlocked Leader, to explore why the future of leadership requires something very different from the old superhero model.

For decades, leaders have been rewarded for projecting cert...

What if the real advantage in the age of AI isn't getting answers faster—but knowing which questions are worth asking?

In this episode of What If?, Leslie Grandy sits down with Prapti Jha, design thinking and innovation consultant, co-founder of We Speak Innovation, and former design thinking catalyst at Ford Motor Company, to explore what happens when AI enters the world of h...

What if entrepreneurship isn't always about starting from scratch—but seeing what an existing business could become?

In this episode of What If? With Leslie Grandy, I sit down with Jon Staenberg, general partner at Agate Hound Fund, the first fund of funds dedicated to search funds, also known as entrepreneurship through acquisition.

Jon has spent decades investing in people, businesses,...

What if the future of leadership isn't about more control, but more permission?

In part two of Leslie Grandy's conversation with Mark Canlis, owner of Seattle's iconic Canlis restaurant, the discussion moves beyond hospitality into a bigger question: what happens to human connection, creativity, and emotional experience in a world increasingly shaped by technology?

In part one, Leslie an...

What if your company isn't defined by what it delivers—but by the human experience it exists to create?

In this episode of What If?, Leslie Grandy sits down with Mark Canlis, owner of Seattle's iconic Canlis restaurant, for part one of a two-part conversation about creative leadership, legacy, hospitality, and culture.

For more than 75 years, Canlis has been one of America's most celebra...

What if the real skill of working with AI isn't knowing what it can do—but knowing when you need to lead?

In this episode of What If?, Leslie Grandy sits down with Leonard Boussioux, assistant professor at the University of Washington's Foster School of Business and adjunct assistant professor at the UW Allen School of Computer Science and Engineering, to explore how humans can collaborate with AI to...

What if the biggest opportunity with AI isn't doing more with less—but doing what wasn't possible before?

In this episode of What If?, Leslie Grandy sits down with Scott Ehrlich, Chief Innovation Officer and Head of Corporate Strategy at Sinclair Broadcast Group, to explore how medi...

What if culture isn't what your company says—but what your people actually experience when it matters most?

In this episode of What If?, Leslie Grandy sits down with Kelly Breslin Wright, veteran executive, former President and COO of Gong, and founder of Culture Driven Sales, to explore a leadership challenge that becomes impossible to ignore as organizations scale:

Misalignment.

What if the biggest risk to your career isn't AI—but waiting for someone else to decide your future?

In this episode of What If?, Leslie Grandy sits down with Dr. Cynthia Benson Mercer, human capital strategist, executive coach, and author of Huma...

What if the biggest risk in your organization isn't moving too fast—but waiting too long?

In this episode of What If?, Leslie Grandy sits down with Sean Atkins, CEO of Dhar Mann Studios and a veteran media and technology leader whose career spans MTV, HBO, Discovery, Yahoo, and Disney—organizations that have all had to navigate massive industry shifts in real time.

Large organizati...

What if transformation isn't something your organization goes through, but something it has to learn to live inside?

In this episode of What If?, Leslie Grandy sits down with Carla Guzzetti, Chief Product Officer at Extreme Networks, to explore what it really takes to lead in environments where disruption is constant and accelerating.

Carla's career spans the early days of digital media, adver...

What if the real difference between ideas that fade and companies that endure isn't creativity—but commitment?

In this episode of What If?, Leslie Grandy sits down with Chris DeVore, founder of Founders' Co-op and one of the Pacific Northwest's most experienced early-stage venture capitalists. Over nearly two decades, Chris has helped launch and fund companies such as Auth0, Outreach, and Remitly, wo...

What if transformation doesn't start with technology, but with curiosity?

In this episode of What If?, Leslie Grandy sits down with Kelly Smith, digital innovation leader, entrepreneur, and founder of Curious Office, to explore what it really takes to reinvent organizations and careers at a moment when AI is reshaping work faster than most cultures can keep up.

Digital transformation, AI trans...

What if product-market fit was never enough?

In this episode of What If?, Leslie Grandy sits down with Marcello Majonchi (Chief Product Officer at Arduino) to explore what happens when the barriers to building collapse—and why that doesn't automatically make innovation easier.

AI, open platforms, and conversational coding tools have democratized creation. Today, more people can prototype...