What If With Leslie Grandy

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.

What If With Leslie Grandy is a business podcast hosted by Leslie Grandy, with 26 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Leslie Grandy hosts What If With Leslie Grandy, a business show with 26 episodes published.

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  Episode #25

  What Leadership Really Requires | #25

  Aug 12, 202618 min

  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?

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  Episode #24

  Curiosity Is the Creative Leader's Advantage | #24

  Aug 5, 202624 min

  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?

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  Episode #23

  What Failure Teaches Creative Leaders | #23

  Jul 29, 202621 min

  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?

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  Episode #22

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

  Jul 22, 202644 min

  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?

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  Episode #21

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

  Jul 15, 202641 min

  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?

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