What If With Leslie Grandy

This last edition of the Creative Velocity Conversations: The Coaches Collection revisits my conversation with Dr. Cynthia Bentzen Mercer.  Cynthia offers a powerful challenge: every individual carries their own human capital—their skills, knowledge, and potential—and they have the agency to deploy it wherever it can create the most value. Agency is no longer optional. It's required. , Organizatio...

This week's edition of the Creative Velocity Conversations: The Coaches Collection reintroduces Hortense le Gentil. Hortense is an executive leadership coach, speaker, and author of Aligned and The Unlocked Leader. Together we explore why the future of leadership requires something very different from the old superhero model. Hortense offers a powerful reframe for this moment: leadership requires...

As we prepare for a new season of the podcast in the fall, we revisit a few episodes about leadership, executive communication, and building human capital. These three conversations are with executive coaches who help leaders become the most effective versions of themselves. Taken together, they offer a roadmap for leading in a world where human judgment, emotional regulation, and empathy are beco...

What if leadership is not about having all the answers, but about creating the conditions where people can do their best thinking? In this special compilation episode of What If? , Leslie Grandy revisits moments from past conversations with leaders, executives, coaches, and culture builders who each offer a different view of what leadership actually demands. Not the polished version from leadershi...

What if curiosity is not a personality trait, but one of the most important leadership skills of this moment? In this special compilation episode of What If?, Leslie Grandy revisits moments from past conversations with leaders, investors, executives, academics, and entrepreneurs who all return to the same underlying idea: curiosity is what keeps people creative, adaptive, and relevant when the wor...

What if failure is not the opposite of success, but one of the ways creative leaders learn how to succeed? In this special compilation episode of What If?, Leslie Grandy revisits moments from past conversations with leaders, founders, investors, executives, and coaches who have all had a close relationship with failure—and have learned to think about it differently. Failure is often treated as evi...

What if the best leaders are not the ones with all the answers, but the ones who know how to ask better questions? In this episode of What If?, Leslie Grandy sits down with Inbal Shani, Chief Product Officer and Head of R&D at Twilio, to explore what leadership looks like when curiosity, judgment, and experimentation matter more than certainty. Inbal's career has taken her from aerospace engineeri...

What if the life you are meant to build is not blocked by a lack of opportunity, but by the limits of what you have allowed yourself to imagine? In this episode of What If?, Leslie Grandy sits down with Erika Rothenberg, bestselling author, leadership coach, speaker, and advocate for audacious expansion, to explore what it takes to stretch beyond last year's version of yourself. Erika's framework...

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...