What If With Leslie Grandy

What if the real creative advantage inside a large company is the willingness to stay uncomfortable long enough for a bold idea to work? In this episode of What If?, Leslie Grandy sits down with Randall Hounsell, veteran digital product executive and longtime Comcast leader, to explore what it really takes to innovate from inside a large, established organization. Randall has spent decades buildin...

What if your second act isn't something you retire into—but something you actively create? In this episode of What If?, Leslie Grandy sits down with Jay Samit, international bestselling author, serial entrepreneur, former Independent Vice Chairman of Deloitte Digital, and author of The Second Act Advantage, to explore why the traditional idea of retirement is overdue for disruption. Jay has spent...

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...

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 human-centered desi...

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, and ideas...

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 and Mark exp...

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 celebrated restau...

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...

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 media, technology, and business model innovation are changing as AI reshapes what can be created, personalized, distrib...

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. As companies gro...

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 Human Capital Investment Strategy , to explore a fundamental shift happening inside organizations: Agency is no longer optional. It's required. As AI resha...

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 organizations are built fo...

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, advertisi...

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,...

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 transform...

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 and ship...

What happens when the spotlight fades and the crown comes off?   In this episode of Ask For An Answer, host Jim Fielding sits down with former Miss USA Olivia Jordan to discuss the raw reality of life after the title. Known for her grace during one of the most infamous moments in Miss Universe history, Olivia opens up about the "evolution behind the headlines". From the high-pressure world of page...

What if the biggest barrier to innovation isn't a lack of ideas, but the way leadership signals who's allowed to have them? In this episode of What If?, Leslie Grandy explores what creative leadership actually looks like inside organizations and why so many companies mistake optics for impact when it comes to innovation. When leaders ask "what if?", they do more than spark ideas. They create psych...

What if the most powerful tool for innovation isn't an answer—but a better question? In the inaugural episode of What If?, host Leslie Grandy introduces the core idea behind the show: "What if" isn't just a question—it's a repeatable practice for unlocking creativity, foresight, and breakthrough thinking. Drawing from her career spanning Hollywood film sets and executive leadership roles at compan...

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