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. ,Organizations don't own that value, and they don't always invest in their employees as compounding assets. But what if they did? What would change?

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 humility and the recognition that "I don't know" is not a weakness. Instead, it invites others to contribute their best thinking, imagine possibilities, and purposely explore ambiguity.  

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 becoming our greatest competitive advantages.  The series kicks off with Chuck Garcia. Chuck was actually the first guest on this podcast, and this conversation demonstrates why he was the perfect person to open the series.

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?

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?  

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?  

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?  

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?

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?

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?  

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?  

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 design. On the surface, AI looks like a powerful accelerator. It can synthesize research, generate personas, benchmark competitors, summarize markets, and prototype ideas at a speed that once seemed impossible. But speed is not the same as insight. And efficiency is not the same as understanding. Together, Leslie and Prapti explore: Why human-centered design depends on real observation, context, and ambiguity How AI can support innovation without replacing the discipline of understanding real human behavior Why AI-generated personas are useful but dangerous when mistaken for actual human insight What organizations lose when they compress time for exploration and questioning Why innovation labs often fail when they are isolated from the rest of the organization How embedding "innovation catalysts" across teams can shift culture more effectively than separating innovation into a protected lab Why the skills once called "soft" are becoming the hardest and most important capabilities in the age of AI How organizations can assess AI maturity by asking employees what problems they are solving or what opportunities they are creating with AI Prapti also introduces the idea that AI maturity is cultural, not just technical. Immature organizations use AI primarily to move faster. More mature organizations use AI as a collaborator—one that helps people challenge assumptions, surface contradictions, and make better decisions. That distinction matters. Because bad processes plus AI do not create innovation. They create faster bad outcomes. This conversation is a reminder that the human role in innovation is not disappearing. It is becoming more essential. AI can support research, synthesis, prototyping, and decision-making, but it cannot fully capture context, emotion, irrational behavior, or lived experience. Human-centered design still begins with humans. And in an AI-accelerated world, the advantage belongs to organizations that protect the time, curiosity, and courage required to ask whether the answer they received is actually the right one. Reflection question: Are you using AI to get to answers faster—or to ask better questions about what truly matters?

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. From venture capital to private equity to winemaking in Argentina, his career has been shaped by curiosity, pattern recognition, and a willingness to ask both sides of the entrepreneurial question: What if it all goes wrong? And what if it works? This conversation explores a different kind of entrepreneurial creativity. Not the creativity of inventing something from nothing, but the creativity of stepping into an existing company with employees, customers, habits, and history and seeing how it can be adapted, strengthened, and carried forward. Together, Leslie and Jon explore: Why search funds are better understood as entrepreneurship through acquisition How acquiring and operating a profitable small business differs from venture-backed invention Why grit, tenacity, humility, and a clear "why" matter more than polish What Jon looks for when backing first-time CEOs Why immigrants, military veterans, and children of family business owners often bring the right temperament for this path How investors evaluate a searcher over time through coachability, humility, judgment, and persistence Why the coming generational handoff of baby boomer-owned businesses creates a powerful opportunity How AI-native operators can modernize "good, boring businesses" faster than legacy owners may be able to imagine Jon also shares the story of how he unexpectedly became a winemaker after a long lunch in Argentina, and why selling his vineyard after 20 years is less an ending than a transition. The thread that remains is community: bringing people together, building trust, creating value, and knowing when to move toward the next thing. This episode is a reminder that creativity is not limited to invention. Sometimes the most creative act is recognizing untapped potential in something that already exists, then having the discipline, humility, and stamina to make it better. Because transformation does not always begin with a blank page. Sometimes it begins with a business that deserves a next chapter. Reflection question: Are you overlooking the possibility inside what already exists because you're waiting for something entirely new?  

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 explored legacy, ritual, culture, and hospitality as invitation. In this continuation, they go deeper into the emotional work of leadership and service, and why deeply human experiences may become even more valuable as AI becomes more embedded in our daily lives.  Mark does not see hospitality as performance. He sees it as relationship. That distinction changes everything. Together, Leslie and Mark explore: Why service can be exhausting and restorative at the same time How emotional labor becomes meaningful when it connects to purpose Why guests often leave Canlis feeling "restored," even when they may not have the words to explain why How fine dining safeguards important emotional moments, from anniversaries to last meals with loved ones Why authentic connection, craft, and presence cannot simply be automated away How small business owners can build cultures where people bring their whole selves to work Why leaders must model vulnerability before asking it of others How play, creativity, and permission help people break free from organizational gravity Mark also offers a powerful challenge to leaders: stop asking employees to perform humanity from a script. Instead, create an environment where people are trusted, known, and invited to care from who they truly are. The conversation closes with a reflection on Creative Velocity and the conditions required for creativity to flourish at work. Leslie reframes velocity not as speed for speed's sake, but as momentum with direction: the ability to break free from the gravitational pull of fear, bias, control, and convention. Because creativity does not thrive in cultures where people are merely told what to do. It thrives where leaders lower the gravity. Where people feel safe enough to try, fail, ask, play, and bring forward what only they can see. And in a world where AI can automate more tasks, the most valuable experiences may be the ones that feel unmistakably human. Reflection question: Are you creating a workplace where people feel controlled into performance, or invited into their full humanity?  

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 restaurants. But Mark does not describe the business first as fine dining, cuisine, service, or even customer experience. He describes it as invitation.  An invitation to matter. An invitation to be seen. An invitation to turn toward one another. That distinction becomes the heart of this conversation. Because when an organization understands what it is truly here to create, it can adapt without losing itself. Together, Leslie and Mark explore: Why hospitality is not performance, but an invitation into relationship How legacy brands can evolve without becoming rigid or nostalgic Why constraints often become fuel for creativity How Canlis reimagined itself during the pandemic by asking what it meant to "turn toward" when traditional dining was impossible Why culture is built through ritual, vulnerability, humor, and shared story How employee experience shapes customer experience long before a guest sits down Why Mark does not train staff to follow scripts, but asks what kind of human they are hoping to become How rituals like the Canlis "Candy Awards," Christmas Eve toasts, open mic nights, shared meals, and playful traditions create trust inside the team Mark challenges a common leadership impulse: to control behavior from the outside in. Instead of scripting hospitality, he starts with desire, humanity, and intrinsic motivation. What does the employee want? Who are they becoming? How can the restaurant help unlock that person? That approach creates a culture where people are not merely executing service standards. They are trusted to create deeply personal, meaningful experiences for guests because they have first experienced belonging, vulnerability, and relationship with one another. Because the invitation to the guest begins with the invitation to the team. And in a world increasingly shaped by automation, monitoring, and efficiency, that kind of human-centered leadership may become more valuable than ever. Reflection question: Are you building a culture that tells people what to do—or one that helps them become the kind of people who know how to care? Next week: Part two continues the conversation with Mark Canlis into creativity, emotional labor, AI, and why deeply human experiences may matter even more in a technology-shaped future.

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 solve complex problems, build new ideas, and expand creative capacity. Leo's work sits at the intersection of operations, machine learning, artificial intelligence, and creative problem solving. His research investigates how humans and AI can work together more effectively—and why simply adding AI to the process doesn't automatically produce better or more original outcomes.  Together, Leslie and Leo explore: Why AI can make people more creative—but may also reduce diversity of ideas if everyone gets the same "excellent" suggestions The difference between human-in-the-loop and AI-in-the-loop thinking Why there is no single formula for when humans should lead and when AI should take more of the exploratory role How students can build confidence, agency, and creative capacity by using AI to bring their own ideas to life Why "vibe coding" is more than a technical skill—it's a way to learn orchestration, judgment, and problem framing How AI-native students may enter the workforce with skills and expectations that leaders are not yet prepared to recognize Why organizations need AI champions, safe access to the best tools, and cultures that encourage knowledge sharing How education must evolve to teach not just AI literacy, but ethics, lifelong learning, metacognition, and leadership Leo also shares how he designs his classroom as a kind of adventure—one where students don't just learn tools, but discover what they are capable of building. By asking students to create real products from their own ideas, he helps them move from anxiety about AI to a sense of creative agency. But the conversation also surfaces a critical warning: AI often recombines what it already knows. It may give you good ideas, but it may give everyone else the same good ideas, too. That means the human role is not disappearing. It is becoming more important. Because the future of human-AI collaboration won't be defined by who can generate the most ideas. It will be defined by who can push beyond the obvious, recognize what matters, and steer the system toward something more original, useful, and human. Reflection question: When you work with AI, are you letting it lead you toward the probable—or are you pushing it toward what only you can imagine?

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, distributed, and scaled. Scott has spent his career navigating major platform shifts—from early OTT subscription services at RealNetworks to digital-first studios, streaming platforms, FAST channels, and AI-enabled media strategy. His perspective is grounded in a simple but powerful idea: A strategy without leverage isn't really a strategy. Today, the mechanics of making things are no longer the biggest constraint. Production is faster. Distribution is broader. AI can generate, iterate, and adapt at speeds that would have been impossible just a few years ago. But that creates a new challenge. When everything can be made, the real question becomes: What should exist at all? Together, Leslie and Scott explore: Why value is shifting from production capability to judgment, relevance, and timing How AI changes the creative process by making iteration faster and less expensive Why personalized storytelling may become a new frontier for media innovation Why AI-native platforms may become the next operating systems for content discovery How business models must evolve when audiences consume information inside AI interfaces How leaders can drive adoption by focusing on one powerful promise: eliminating the toil of work Scott also offers a grounded view of where most organizations are in the AI adoption curve. Before companies can transform workflows, they often need to use AI to improve existing ones. The breakthrough, he argues, starts with helping people remove the frustrating, repetitive work that drains their time and attention. But the bigger opportunity is still ahead. Too much of the current AI conversation is focused on efficiency: fewer people, fewer steps, faster processes. Scott challenges leaders to look beyond that and ask a more expansive question: What new things can we do now that we could never do before? Because the future of innovation won't belong only to those who move faster. It will belong to those who can recognize where new leverage is forming—and use it to create something more meaningful. Reflection question: Are you using AI only to streamline what already exists—or to imagine what could exist next?

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 grow, what once felt clear and shared begins to fragment. Leaders use the same words—innovation, customer obsession, growth—but mean different things. Teams move in parallel, not together. And the gap between stated values and lived experience quietly widens. Then AI enters the picture—and amplifies everything.  AI doesn't just accelerate work. It exposes inconsistencies. It surfaces where culture is unclear, where leadership signals are mixed, and where organizations say one thing—but reward another. Together, Leslie and Kelly explore: Why culture is defined by what happens when people take risks, not what's written on the wall How to diagnose misalignment by asking a simple question: Does everyone describe our purpose the same way? Why companies often lose sight of their "why" as they scale—and what that costs them The critical role of leaders as "Chief Belief Officers" in aligning and inspiring teams How AI is leveling the playing field, making people and leadership the true differentiators Why psychological safety and honest conversations matter more in moments of disruption How to build cultures where experimentation is expected—and failure is not punished The risk of treating employees like outputs instead of humans—and how that erodes performance Kelly also shares lessons from her early experience running a door-to-door sales business—where resilience, adaptability, and emotional intelligence weren't theoretical concepts, but daily survival skills. Those same capabilities, she argues, are now essential for navigating modern organizations. Because while AI can increase speed, efficiency, and access to information, it cannot replace what great cultures create: Belief, trust, and the willingness to take risks together. This episode is a clear reminder that in a world where technology is advancing rapidly, the organizations that win won't just be the most technically capable. They'll be the most aligned. Reflection question: If you asked your leadership team to describe your company's purpose, would you hear one answer—or many?  

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 reshapes work—automating execution, accelerating analysis, and leveling access to information—the rules of value creation are changing. Effort alone is no longer enough. Titles are less stable. And the idea that "if I work hard, someone will notice" is quickly becoming outdated. Instead, both individuals and organizations are being forced to rethink what human contribution actually means. Together, Leslie and Cynthia explore: Why human capital should be treated as a compounding investment, not a cost center The critical difference between having value and articulating value Why employees must take ownership of their careers—rather than outsourcing it to managers or companies How to define your "aspirational next" and actively build toward it The danger of reducing people to roles, titles, or "boxes"—instead of seeing them as adaptable "puzzle pieces" What leaders get wrong about layoffs, talent mobility, and long-term workforce strategy Why transparency, communication, and intentionality matter most during disruption How AI is shifting value toward creativity, judgment, empathy, and complex problem-solving Cynthia also offers a powerful reframe: 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. Organizations don't own that value. They invest in it—and must continuously earn the right to keep it. This creates a new kind of tension. Companies say people are their greatest asset. But how they hire, develop, move, and sometimes let go of those people reveals what they actually believe. Because in a world where technology is advancing rapidly, the advantage doesn't go to those who simply adapt. It goes to those who take ownership.

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 for execution. They scale what works. They reduce ambiguity. They optimize for predictability. But in moments of transformation, those same strengths become constraints. Because by the time something looks safe—your audience has already moved on.  This conversation explores what it actually takes to lead inside that tension. Together, Leslie and Sean unpack: Why creative leadership isn't about having the best idea—but having the courage to act under uncertainty How to distinguish between trends and true behavioral shifts The three signals Sean uses to evaluate opportunities: velocity of adoption, business model clarity, and historical precedent Why waiting for certainty is often the most dangerous strategy in a changing market How curiosity becomes valuable only when paired with discernment and decision-making Why creativity exists in every function—from finance to operations—not just "creative roles" The hidden cost of homogeneous teams—and how diverse inputs drive better outcomes What it means to intentionally hire people who challenge culture—not just fit it Sean also shares a candid look at what it's like to be a "maverick" inside large organizations—where leaders say they want disruption, but often resist the discomfort that comes with it. He reflects on the personal tradeoffs, the political realities, and the importance of learning how to navigate systems—not just challenge them. The conversation also turns to AI, and the uncertainty it introduces. Rather than offering false clarity, Sean takes a pragmatic view: this is a moment of real disruption, real anxiety, and real opportunity—all at once. Because the future won't be shaped by those who wait for the path to be clear. It will be shaped by those willing to step into ambiguity—and learn faster than the system can resist them. Reflection question: Where are you waiting for certainty—when the real opportunity requires you to move first?

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, advertising, and enterprise technology industries that have repeatedly reinvented themselves. That experience shaped how she sees change: not as chaos to survive, but as a pattern to recognize and navigate.  As AI lowers the barrier to building and dramatically increases what teams can produce, leaders face a new challenge: how to balance speed with judgment, experimentation with accountability, and innovation with real customer value. Together, Leslie and Carla explore: Why the most effective leaders learn to "see the pattern in the chaos" How to balance delivery pressure with the need for exploration and future bets Why protecting against obsolescence is just as critical as hitting quarterly goals How to reframe failure as a learning loop and reduce fear inside teams What it means to take intelligent risk, not just low risk How AI is changing not just productivity, but who does the work and how roles evolve Why curiosity must be operationalized inside culture, not just encouraged Carla also shares how her teams are approaching AI in high-stakes environments where reliability matters—introducing it in stages, aligning it to real "jobs to be done," and maintaining a human-in-the-loop mindset when trust is non-negotiable. The conversation surfaces a critical tension: AI makes it easier than ever to build, test, and generate ideas—but that doesn't guarantee better outcomes. In fact, it raises the bar for leaders to stay anchored in what matters most. Because when everything is moving faster, clarity doesn't come from more tools. It comes from knowing exactly who you serve—and why. Reflection question: Are you chasing what's possible or staying grounded in what actually creates value for your customer?

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, working at the earliest moments when ideas are still fragile and the path forward is uncertain. Venture capital is often described as a search for bold ideas. But Chris argues the real work is discernment—deciding which founders and which problems deserve years of belief, capital, and effort. Surrounded by endless possibilities, the challenge isn't imagination. It's choosing what to commit to and what to leave behind.  Together, Leslie and Chris explore: Why many talented idea-generators struggle to become founders The tension between divergent thinking and the discipline to converge on a single path Why investors look for founders who are already "doing the thing," not just thinking about it How the best founders balance confidence with humility—and conviction with the ability to listen Why most startups fail not because of technology, but because of breakdowns in learning from customers How venture capital evaluates opportunities through three lenses: the team, the technology moment, and the potential scale Why AI is lowering the barrier to building software—but raising the bar for differentiation Chris also offers a clear-eyed view of today's AI wave. The ability to prototype and build software has never been easier. But that abundance creates a new challenge: signal versus noise. When everyone can create products quickly, what matters most becomes judgment, focus, and the ability to solve real problems that customers truly care about. This conversation is a candid look inside the founder–investor relationship—and a reminder that innovation is not just about opening possibilities. It's about choosing which ones are worth pursuing. Because creativity begins with imagination. But progress begins the moment someone says: "I'm doing this." Reflection question: Are you exploring ideas—or have you committed to solving a problem that truly matters?  

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 transformation, cultural transformation: these are often treated like implementation problems. Roll out the tools. Train the teams. Check the box. But real transformation doesn't begin with systems. It begins with a question. With the willingness to slow down, challenge assumptions, and ask what's actually happening inside an organization and inside ourselves as leaders. This conversation dives into: Why curiosity is not a personality trait, but a practice and operating mode How culture quietly teaches people which questions are safe and which are not Why bold ideas often come from the "wrong" roles, titles, or corners of the org chart How risk, failure, and intuition shape real innovation more than credentials or job descriptions What AI is amplifying inside organizations for better and for worse Why the future belongs to polymaths, pattern matchers, and first-principles thinkers The uncomfortable truth about job compression, reinvention, and choosing the "red pill or blue pill" Kelly shares hard-earned lessons from leading digital change at companies like Starbucks, MGM Resorts, Athletic Greens, and Hagerty, as well as what he looks for when backing early ideas in a world where building is easy but building something worthwhile is not. Together, Leslie and Kelly unpack why curiosity creates agency, why asking "What if we did this differently?" is often riskier than proposing confident answers, and why organizations that punish questions end up protecting the past instead of preparing for the future. This episode is for leaders, builders, and teams who feel the ground shifting beneath them and know that doing more of the same won't be enough. Because the real divide ahead isn't technical. It's between those willing to ask better questions and those clinging to old ones. Reflection question: If you had to reinvent your professional life from scratch today, what would curiosity pull you toward and what would fear try to hold you back from?  

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 working software than at any point in history. That sounds like an innovation boom and in many ways, it is. But when everyone can build, the real question shifts: It's no longer Can you build it? It's Why will anyone choose yours? Together, Leslie and Marcello unpack: Why product-market fit has never been enough The concept of the "MVP cubed": viable, valuable, and validating How company stage (startup vs. hyperscaler vs. scale-up) fundamentally changes product outcomes Why scaling from prototype to production is where most leaders miscalculate The risks of AI-driven acceleration, especially technical debt and architectural shortcuts Why product management is becoming more business-critical, not less How emotional experience, not just functionality, differentiates great products Marcelo argues that AI changes the journey, not the destination. The tools may be faster. Prototyping may be cheaper. But judgment, discipline, customer trust, and emotional connection still determine whether something endures. They also explore a surprising thread: why physical books still matter in a digital world—and what that teaches us about product experience, tactile design, and the return of physicality after decades of "software-defined everything." Because even in an AI-accelerated world, customers don't reward speed. They reward value. Reflection question: If anyone can build what you're building, what makes yours meaningful and worth trusting?  

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 pageantry in Los Angeles to finding peace and rebuilding her life in Tulsa, Olivia shares how to navigate identity shifts, personal growth, and the journey of reinvention. Episode Timestamps & Key Takeaways: 01:17 – The "Buffet Bond": Jim and Olivia reflect on their nine-year friendship and the "rewrites" they've witnessed in each other's lives. 12:04 – Stepping Into New Roles: Olivia discusses the "surprise fulfillment" of her life: transitioning from being in front of the camera to becoming an acting coach. 13:01 – Reimagining the Dream: Why the pandemic and motherhood prompted a move from Los Angeles back to Tulsa to build a "different kind of dream". 18:24 – Building the Confidence Muscle: How pageantry served as a strategic tool to overcome personal struggles with confidence and prepare for the pressures of "adult" life. 19:52 – The Pageant Hangover: A candid look at the "baptism by fire" of being Miss USA and the difficult transition of reclaiming control over your own schedule. 23:50 – The Power of the Pivot: Reconnecting with her hometown and the healing required to return to Tulsa after early life trauma. This is not just a story about pageants or Hollywood. It is about growth, vulnerability, service, and stepping into your most realized self. If you are in a season of reinvention or asking what comes next, this episode is your invitation.   ✨Follow Jim Fielding & Ask For An Answer: 💼Instagram: jimfielding🌐Podcast: Ask For An Answer Try Leslie's Emotional Regulation Coach GPT and get help regulating your emotions today

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 psychological permission the signal that curiosity, challenge, and early thinking are not only allowed, but expected. Without that signal, teams default to safe bets, incremental improvements, and inherited assumptions that quietly slow innovation to a crawl. Drawing from her experience at Amazon, T-Mobile, and Best Buy, Leslie breaks down: Why innovation labs often create the illusion of progress while isolating creativity from execution How segregating "innovators" teaches the rest of the organization that innovation isn't their job What happens when brilliant ideas can't cross the boundary from invention to operations How cultural values like "data-driven", "continuous improvement", and "team unity" can unintentionally suppress breakthrough thinking Why creative velocity depends on leaders modeling intellectual bravery—not protecting the status quo You'll hear a behind-the-scenes story of T-Mobile's Cameo product, an idea that failed not because it lacked insight, but because the organization wasn't designed to support what it imagined. Leslie contrasts that with Amazon's dual operating model: data-driven optimization paired with judgment-based invention, and why Jeff Bezos warned against the "tyranny of data." This episode is for leaders who want more than performative innovation. For teams tired of being reactive. And for organizations ready to stop outsourcing creativity to labs, decks, or consultants and start embedding it everywhere. Because creative leadership isn't about protecting existing systems. It's about consistently inviting better ones to emerge. Reflection question: What if the signal your culture is sending isn't "be creative," but "don't rock the boat"?

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 companies like Apple, Amazon, T-Mobile, RealNetworks, and Best Buy, Leslie shares how two simple words reshaped the way she solves problems, challenges assumptions, and builds resilient strategies in the face of uncertainty. In this episode, you'll learn: Why creativity isn't an artistic talent—but a universal problem-solving skill How asking "what if" helps leaders move from incremental thinking to exponential outcomes The five deliberate ways to apply "what if" to reframe problems, break rules, flip assumptions, and anticipate unintended consequences Real-world examples of how "what if" thinking led to industry-shaping innovations—from subscription video models to curbside pickup How to stop reacting to change and start designing the future you actually want This episode sets the foundation for the What If? method—a structured approach that helps executives, functional leaders, and teams think bigger, see around corners, and use AI as a creative collaborator, not a crutch. Whether you lead a Fortune 500 team, manage a critical function like finance or operations, or simply feel stuck playing it safe, this podcast is for you. Because innovation doesn't start with better answers. It starts with better questions. Challenge for this week: Ask yourself—What if the thing holding me back isn't the problem, but the way I'm seeing it?  

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