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What If With Leslie Grandy

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by Leslie Grandy

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23 episodes

Updated Daily

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Podcast Overview

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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Publishing Since

2/24/2026

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Recent Episodes

July 22, 2026

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: <ul> <li dir="ltr" role="presentation">Why great leaders do not need to know everything, but they do need to stay curious</li> <li dir="ltr" role="presentation">How asking questions can become a strength rather than a signal of insecurity</li> <li dir="ltr" role="presentation">Why failure only becomes valuable when teams communicate honestly about risk, blockers, and learning</li> <li dir="ltr" role="presentation">How leaders can create environments where experimentation is encouraged but not reckless</li> <li dir="ltr" role="presentation">Why customer problems should ground innovation, even when teams are building toward a future market</li> <li dir="ltr" role="presentation">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</li> <li dir="ltr" role="presentation">Why innovation must happen across the whole company, not just inside isolated labs</li> <li dir="ltr" role="presentation">How companies get AI transformation wrong when they start with fear of missing out instead of purpose</li> <li dir="ltr" role="presentation">Why the better AI question is not "What is our AI strategy?" but "Where can better tools help this business operate more successfully?"</li> <li dir="ltr" role="presentation">Why AI should sharpen human thinking, not replace it</li> </ul> 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?

July 15, 2026

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: <ul> <li dir="ltr" aria-level="1"> Why expansion is not about doing more, but seeing more possibility </li> <li dir="ltr" aria-level="1"> How grit, grace, and glitz work together to support sustainable growth </li> <li dir="ltr" aria-level="1"> Why saying no can be one of the most powerful ways to reclaim capacity </li> <li dir="ltr" aria-level="1"> How to recognize when a responsibility is building you versus draining you </li> <li dir="ltr" aria-level="1"> Why fear is often the biggest blocker to audacious expansion </li> <li dir="ltr" aria-level="1"> How writing down a goal and saying it out loud can move an idea closer to action </li> <li dir="ltr" aria-level="1"> Why curiosity and agency are essential to stepping into a bigger version of your life </li> <li dir="ltr" aria-level="1"> How failure builds resilience when we treat it as part of the process rather than proof we should stop </li> <li dir="ltr" aria-level="1"> Why AI can be a useful tool for growth, but cannot replace meaningful human connection </li> <li dir="ltr" aria-level="1"> How movement, reset rituals, and flow help us return to expansion mode when we feel overloaded </li> </ul> 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?

July 8, 2026

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: <ul> <li dir="ltr" aria-level="1"> Why building something new inside a big company requires grit, patience, and comfort with ambiguity </li> <li dir="ltr" aria-level="1"> How large organizations can attract both people who seek stability and people who want to create new things </li> <li dir="ltr" aria-level="1"> Why bold ideas naturally create discomfort—and why leaders need to normalize that discomfort </li> <li dir="ltr" aria-level="1"> How "antibodies" inside large companies often emerge when new ideas challenge the status quo </li> <li dir="ltr" aria-level="1"> Why resilience and adaptability are both essential when early versions fail </li> <li dir="ltr" aria-level="1"> How Randall thinks about learning from failed products without taking failure personally </li> <li dir="ltr" aria-level="1"> Why strong vision matters more than ever as AI generates more ideas, options, and hypotheses </li> <li dir="ltr" aria-level="1"> How AI can help product teams test, shape, and de-risk ideas faster, while still requiring humans to own strategy and judgment </li> <li dir="ltr" aria-level="1"> Why innovation cannot depend only on isolated labs or special projects, but must become part of how teams work every day </li> </ul> 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?

23 total episodes available

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What is 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.
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: Yes, this podcast regularly features guests.

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