What If With Leslie Grandy

Leslie Grandy
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This podcast is about curiosity, what it means to be creative, and why asking "What if?" can transform how things work and help you build a resilient future. We'll look at how asking better questions can unlock transformative thinking and what happens when you challenge assumptions and imagine what could be, rather than accepting what is.

  1. Aug 12

    What Leadership Really Requires | #25

    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 leadership books or corporate values statements. The real version. The version that asks whether you act like people are your greatest asset when budgets tighten, change gets hard, or performance pressure rises. The version that requires vulnerability before you ask it of others. The version that can admit, "I don't know." The version that understands discomfort, disagreement, and pushback are not always threats to culture, but sometimes the very things that keep it alive. This episode brings together insights from previous What If? guests including Cynthia Malthouse, Kelly Breslin Wright, Marc Camillus, Chuck Garcia, Sean Atkins, and Hortense LeGentil, each exploring a different dimension of leadership. Together, these voices explore: Why human capital is different from every other asset because people have agency How leaders reinforce change through what they celebrate, correct, and model Why "people are our greatest asset" only matters if leaders make decisions that prove it How getting the people side right gives organizations a stronger foundation for everything else Why clarity is kindness, especially when leaders are asking people to join them in change How vulnerability from leaders creates permission for others to show up honestly Why admitting "I don't know" can prevent self-inflicted harm and build trust How psychological safety depends on leaders who can sit with discomfort Why the person who pushes back may be protecting the culture from becoming too comfortable How the "superhero leader" model exhausts leaders and limits the growth of everyone around them Across these conversations, a clear pattern emerges: leadership is not a performance of certainty. It is a daily practice of alignment. It shows up in whether leaders model the change they expect from others. It shows up in whether they celebrate the behavior they want to see more of. It shows up in how they respond to challenge, whether they listen to people who make them uncomfortable, and whether they are willing to name what they do not know instead of pretending. The leaders featured in this episode remind us that culture is not built by intention alone. It is built by repeated behavior. If you say people matter, people will watch what happens when pressure rises. If you say experimentation matters, people will watch what happens when something fails. If you say honesty matters, people will watch what happens when someone tells the truth. And if you say leadership is about growth, people will watch whether you are still growing too. This compilation is an invitation to think less about the image of leadership and more about its impact. Because the question is not whether you have the title, the authority, or the answer. The question is: how do you want to be remembered as a leader? Reflection question: What leadership behavior are you modeling every day, whether you intend to or not?

  2. Aug 5

    Curiosity Is the Creative Leader's Advantage | #24

    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 world around them keeps changing. Across these conversations, curiosity shows up in different ways. For some guests, it is a lifelong habit of questioning what others accept at face value. For others, it is the reason they can navigate ambiguity, stay open to new tools, reinvent themselves, or build teams that are willing to experiment. And in an AI-accelerated world, curiosity is no longer optional. AI can retrieve information quickly. It can synthesize, summarize, and produce answers faster than any human. But it cannot guarantee that the first answer is the most meaningful one. It often gives the most probable answer, not necessarily the most original, useful, or human one. That is where curiosity matters. This episode brings together insights from previous What If? guests including Kelly Smith, Jon Staenberg, Jay Samit, Prapti Jha, Katherine Elkins, Carla Guzzetti, Scott Ehrlich, and Sean Atkins, each offering a different lens on why curiosity matters for creative leadership. Together, these voices explore: Why curiosity is often the common thread among high performers How curiosity helps leaders move beyond ego, certainty, and default answers Why the most successful people often refuse to take the world at face value How curiosity can stay alive across career stages, industries, and even into a second act Why organizations must create psychological safety for questioning, experimentation, and learning How AI rewards people who keep pushing past the obvious answer Why prompting AI well is less about technical skill and more about critical engagement How companies that do not encourage curiosity may struggle as AI reshapes work Why curiosity helps leaders spot meaningful trends instead of simply reacting to hype How creative leadership depends on giving people the time, permission, and culture to explore The compilation makes one thing clear: curiosity is not passive. It is active, sometimes uncomfortable, and often disruptive. It asks why. It challenges the default. It follows the question that does not yet have a clean answer. It refuses to confuse familiarity with truth. And for leaders, that matters. Because when teams are overloaded with execution, penalized for slowing down to ask better questions, or rewarded only for having fast answers, curiosity disappears. People conform. Ideas narrow. The organization becomes efficient at repeating what it already knows. But the future belongs to teams that can keep learning. The leaders featured in this episode show that curiosity is the condition that makes creativity possible. It allows people to stay open, keep experimenting, follow new patterns, and build a culture where "I don't know" becomes the beginning of discovery rather than a liability. In the age of AI, that kind of culture is not a nice-to-have. It is the baseline for doing genuinely creative work. Because the leaders who will thrive are not the ones who accept the first answer. They are the ones curious enough to keep asking better questions. Reflection question: Where have you accepted the obvious answer, when curiosity might lead you somewhere more useful?

  3. Jul 29

    What Failure Teaches Creative Leaders | #23

    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 evidence that something, or someone, was not good enough. From school onward, many of us are trained to connect failure with inadequacy, punishment, or shame. So we learn to play smaller. We avoid risk. We compress our thinking. We look for certainty before we move. But creative leadership requires a different relationship with failure. It requires the ability to test assumptions, take intelligent risks, listen deeply, adapt quickly, and stay curious long enough to understand what went wrong. This episode brings together insights from previous What If? guests including Kelly Smith, Marcelo Majonchi, Kelly Breslin Wright, Chuck Garcia, Chris DeVore, and Sean Atkins, each offering a different perspective on what failure reveals and how leaders can use it to grow. Together, these voices explore: Why failure is often misused as a label when an outcome simply did not match expectations How leaders distinguish between high-quality failure and failure that comes from ignoring what they already knew Why prioritizing business performance over human wellbeing can become a failure that stays with a leader How product builders learn from lack of product-market fit Why failure should be expected when teams are building something that has not existed before How resilience, adaptability, and risk tolerance become leadership muscles Why admitting "I don't know" is not weakness, but a necessary part of learning How great teams normalize experimentation without lowering standards Why startups often fail when founders lack a strong feedback loop between what customers say and what they build How failure can sharpen judgment when leaders are willing to interrogate it instead of defend against it Across these conversations, one theme becomes clear: failure is only useful when it is examined. It is not enough to reframe failure as growth and move on. The real value comes from owning it, questioning it, and understanding the pattern it reveals. Was the assumption wrong? Was the customer feedback ignored? Was the team moving too fast to notice the risk? Was the leader trying to appear certain instead of staying curious? Was the failure actually a stumble—or was it a signal? The leaders featured in this episode do not romanticize failure. They do not suggest that every failure is automatically noble, productive, or necessary. Instead, they show that failure becomes meaningful when it creates better judgment, stronger resilience, clearer communication, and a more honest relationship with uncertainty. Because creative leaders are not the people who avoid failure. They are the people who know how to learn from it without letting it define them. Reflection question: What failure are you ready to examine more honestly, not to relive it, but to understand what it can teach you?

  4. Jul 22

    What If Great Leaders Don't Have All the Answers? with Inbal Shani | #22

    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 engineering and applied science to leadership roles at Amazon, GitHub, Microsoft, and Twilio. Across that journey, she has built a deep understanding of complex systems, not just how individual components work, but how they connect, interact, and create something larger together. That systems mindset shapes the way she thinks about product, culture, innovation, and AI. Together, Leslie and Inbal explore: Why great leaders do not need to know everything, but they do need to stay curious How asking questions can become a strength rather than a signal of insecurity Why failure only becomes valuable when teams communicate honestly about risk, blockers, and learning How leaders can create environments where experimentation is encouraged but not reckless Why customer problems should ground innovation, even when teams are building toward a future market What Inbal learned from the cancellation of the Amazon Fire Phone, and how that failure produced assets that later helped fuel Alexa and Amazon's last-mile capabilities Why innovation must happen across the whole company, not just inside isolated labs How companies get AI transformation wrong when they start with fear of missing out instead of purpose Why the better AI question is not "What is our AI strategy?" but "Where can better tools help this business operate more successfully?" Why AI should sharpen human thinking, not replace it Inbal offers a clear warning for this moment: when companies adopt AI because the board says they need an AI strategy, they often drive the wrong behavior. The technology becomes a mandate instead of a meaningful answer to a real problem. Purpose has to come first. That means understanding the customer problem, the employee problem, or the business friction AI is meant to solve before deciding how to use it. It also means refusing to outsource judgment. AI can accelerate work, help teams prototype faster, support engineers, personalize customer experiences, and reduce friction. But Inbal cautions against delegating the thinking itself. The human work still matters: curiosity, creativity, judgment, subject-matter expertise, and the ability to know whether an answer is merely adequate or actually great. This conversation is a reminder that leadership in an AI-accelerated world is not about pretending to have certainty. It is about building the conditions where people can ask better questions, fail forward, learn quickly, and use technology with purpose. Because the leaders who matter most now are not the ones who already know. They are the ones still willing to learn. Reflection question: Where are you looking for an answer too quickly, when the better leadership move might be to ask a more purposeful question?

  5. Jul 15

    Building the Capacity for What's Possible with Erika Rothenberg | #21

    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 of grit, grace, and glitz offers a practical and deeply human way to think about growth. Grit gives us the resilience to keep going. Grace gives us the self-awareness to pause, reset, and stop carrying what no longer serves us. And glitz reminds us to celebrate the small wins, the daily progress, and the moments of gratitude that keep us connected to why the work matters. Together, Leslie and Erika explore: Why expansion is not about doing more, but seeing more possibility How grit, grace, and glitz work together to support sustainable growth Why saying no can be one of the most powerful ways to reclaim capacity How to recognize when a responsibility is building you versus draining you Why fear is often the biggest blocker to audacious expansion How writing down a goal and saying it out loud can move an idea closer to action Why curiosity and agency are essential to stepping into a bigger version of your life How failure builds resilience when we treat it as part of the process rather than proof we should stop Why AI can be a useful tool for growth, but cannot replace meaningful human connection How movement, reset rituals, and flow help us return to expansion mode when we feel overloaded Erika challenges the idea that growth requires constant grind. Instead, she offers a more integrated way forward: one that asks us to stretch, but also to notice when we need space; to work hard, but also to celebrate progress; to pursue expansion, but not at the expense of ourselves. This conversation is a reminder that what feels possible is often shaped by what we have practiced believing, naming, and pursuing. And sometimes, the first act of expansion is simply telling the truth about what you want. Because when you start saying yes to the right things, no to what drains you, and grace to yourself along the way, you begin building the capacity for a bigger future. Reflection question: What possibility have you kept just outside your reach because you have not yet given yourself permission to stretch toward it?

  6. Jul 8

    The Intrapreneur's Creative Advantage: Comfort with Discomfort with Randall Hounsell | #20

    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 building new products and businesses inside Comcast, including co-founding Xfinity Mobileand helping scale it to more than 5 million subscriber lines. He has also led innovation across connected living, IoT, internet, mobile, digital products, and the connected home experience. But this conversation is not just about product development. It is about the mindset required to be an intrapreneur. Together, Leslie and Randall explore: Why building something new inside a big company requires grit, patience, and comfort with ambiguity How large organizations can attract both people who seek stability and people who want to create new things Why bold ideas naturally create discomfort—and why leaders need to normalize that discomfort How "antibodies" inside large companies often emerge when new ideas challenge the status quo Why resilience and adaptability are both essential when early versions fail How Randall thinks about learning from failed products without taking failure personally Why strong vision matters more than ever as AI generates more ideas, options, and hypotheses How AI can help product teams test, shape, and de-risk ideas faster, while still requiring humans to own strategy and judgment Why innovation cannot depend only on isolated labs or special projects, but must become part of how teams work every day Randall makes a clear distinction between optimizing what already exists and creating something meaningfully new. Optimization feels comfortable. You can look at a dashboard, find a problem, and improve the metric. But bold ideas ask more of people. They ask teams to operate in ambiguity. They ask leaders to hold a vision before the data is complete. They ask organizations to tolerate early failure without shutting down the learning that makes success possible. And that is where the intrapreneur's creative advantage begins. Not in avoiding discomfort, but in developing the capacity to keep moving through it. As AI becomes more integrated into product work, Randall sees enormous opportunity for teams to form hypotheses, test assumptions, prototype faster, and validate ideas more efficiently. But he also offers an important caution: vision is not something AI can provide on its own. The human responsibility is still to know where the company is going, why it matters, and how each idea fits into a larger strategy. Because inside a large organization, creativity is not just about having ideas. It is about building the culture, clarity, and stamina required to pursue the right ones. Reflection question: Where are you choosing the comfort of optimization when your next breakthrough may require the discomfort of a bigger idea?

  7. Jul 1

    Curiosity & Agency: The Stars of Your Second Act with Jay Samit | #19

    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 his career running toward disruption rather than away from it. He has pioneered breakthrough technologies used by billions, helped grow companies including LinkedIn, Sony, and Universal Studios, advised Fortune 500 companies, raised hundreds of millions for startups, and more recently launched a career as an artist exploring the impact of AI and technology on human life. Now, he is turning his attention to one of the biggest personal disruptions many people will face: what happens when work no longer defines us? Together, Leslie and Jay explore: Why retirement can become a dangerous myth when it removes purpose, structure, identity, and connection How curiosity and agency become essential skills for navigating a meaningful second act Why the question should shift from "What will I do in retirement?" to "What can the world gain now that I have time?" How AI can help people rediscover purpose, build businesses, learn new skills, and act on ideas faster than ever before Why Jay created "Digital Jay," an AI mentor designed to help readers personalize their second-act journey How disruption is not about what happens to you, but how you respond Why purpose, human connection, creativity, and contribution are central to longevity and fulfillment What high performers often misunderstand about identity when their title, routine, or professional status changes Jay challenges the familiar idea that retirement is a finish line. For many people, it is actually an identity disruption. The structures that once gave life shape—meetings, titles, colleagues, goals, performance, recognition—suddenly disappear. And without curiosity, agency, and a clear sense of purpose, that freedom can feel less like liberation and more like drift. But Jay offers a different possibility. Your second act can become the most creative chapter of your life. It can be a time to apply hard-earned wisdom, build something new, solve a problem that matters, mentor others, create art, launch a business, strengthen community, or leave a legacy that extends beyond achievement. And AI, rather than being something to fear, can become a powerful force multiplier—especially for people willing to keep learning. Because the people who thrive in their second act will not be the ones who wait for the world to tell them what comes next. They will be the ones curious enough to ask what if—and agentic enough to act on the answer. Reflection question: What wisdom, curiosity, or unfinished idea are you carrying that could become the beginning of your second act?

  8. Jun 24

    The Superpower of I Don't Know with Hortense le Gentil | #18

    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 certainty. They were expected to have the answers, set the direction, stay composed, and absorb the pressure. But in a world moving faster than any one person can fully understand—especially as AI reshapes work, decisions, and expectations—that model is becoming impossible to sustain. And maybe the real breakthrough begins when leaders stop pretending it is. Together, Leslie and Hortense explore: Why the "superhero leader" model leaves leaders exhausted and teams disconnected How saying "I don't know" can build trust instead of weakening authority Why self-awareness is the foundation for more human leadership How fear, perfectionism, and old success patterns become leadership traps Why leaders must learn to invite their fears to the table without letting those fears lead How AI makes empathy, intuition, creativity, and emotional nuance more important—not less Why leaders need to stop competing with AI and start deepening the capabilities that make them human How to create environments where people feel safe enough to question, experiment, fail, and grow Hortense offers a powerful reframe for this moment: leadership is not about being the smartest person in the room. It is about creating the conditions where others can contribute what they see, know, question, and imagine. That starts with humility. Not the passive kind. The courageous kind. The kind that says: I do not have all the answers, and I am willing to learn with you. Because in a world where change is constant and certainty is scarce, "I don't know" is not a weakness. It may be the beginning of trust, creativity, and real transformation. Reflection question: Where are you still trying to lead by having all the answers, when your team may need you to model the courage to learn?

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This podcast is about curiosity, what it means to be creative, and why asking "What if?" can transform how things work and help you build a resilient future. We'll look at how asking better questions can unlock transformative thinking and what happens when you challenge assumptions and imagine what could be, rather than accepting what is.

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