Choosing Leadership with Sumit Gupta

Sumit Gupta
  • 5.0 (2)
  • Business
  • Updated Weekly

As a leader, you are always making choices. Even when you think you have no choice. And if you are unable to make a decision, you are choosing to stay in a state of indecision. The only question is - are your choices taking you where you want to go? I am Sumit Gupta, and this is "Choosing Leadership" - a podcast for high performers with big dreams - who know deep inside that there is more. This is a podcast for people who know they are more powerful than the level they are currently playing. I have spent a long time feeling powerless, and that is why I see where you are powerful even when you cannot. I dare to say what most people would not. I dare to speak to the "tremendous power" which you already have rather than what you believe are your strengths and limitations. This podcast is called "choosing leadership" - because that is what leadership is - a choice. The choice to step into the unknown. The choice to see fear as a friend. The choice to take courageous action rather than waiting for readiness. Join Sumit in exploring this question when it comes to your leadership. In each moment of life, are you Deploying Yourself or not? In each moment of life, are you Choosing Leadership or not?

  1. Leadership Journeys [286] - Roisin Wood - "When you know what exclusion feels like, you spend your life building belonging."

    Jun 2

    Leadership Journeys [286] - Roisin Wood - "When you know what exclusion feels like, you spend your life building belonging."

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, I attempt to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. In this powerful conversation, Roisin Wood shares what leadership looks like when you choose courage, inclusion, and humanity over division. From growing up amid sectarian conflict in Northern Ireland to leading conversations around belonging, justice, and social change, Roisin offers hard-earned wisdom for leaders navigating polarized and emotionally charged environments. This episode will challenge you to rethink how you handle disagreement, build trust across differences, and create spaces where people genuinely feel they belong. You’ll also discover why football, community, and face-to-face connection still matter deeply in an increasingly disconnected world. If you’re leading a team, a company, or even your own family through uncertainty and tension, this conversation will leave you thinking differently about the kind of leader the world needs now. You can find Roisin Wood at the links below https://www.linkedin.com/in/roisin-wood-342b5524/https://communityfoundationni.org/  In the interview, Roisin shares “Leadership isn’t about avoiding difficult conversations. It’s about having the courage to sit across from people you disagree with and still choose humanity.”  “Belonging changes everything. When people feel seen, valued, and included, communities become stronger and leadership becomes transformational.”  “The people who shaped me most weren’t the ones who agreed with me — they were the ones who challenged me to listen more deeply.”  “You cannot build peace while refusing to engage with people who hold opposing views. Real leadership lives inside uncomfortable dialogue.”  “Football showed me something powerful: when people share a purpose, barriers that once felt impossible to cross suddenly begin to disappear.”  “Standing up for justice will often invite criticism, but silence has never been the thing that changes societies.”  “Technology can connect us instantly, but it can never replace the power of genuine human connection and face-to-face belonging.”  “Young leaders need to understand this early: courage isn’t loud. Sometimes courage is simply staying true to your values when it would be easier not to.”  “Kindness, curiosity, and bravery are not soft leadership traits — they are the foundation of creating meaningful change.”  “Leadership is not just about managing organizations. It’s about building a world where every person feels they have a place and that they matter.”

    51 min
  2. Leadership Journeys [285] - Lokendra Tomar - "Real freedom is living beyond other people’s definitions of success."

    May 26

    Leadership Journeys [285] - Lokendra Tomar - "Real freedom is living beyond other people’s definitions of success."

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, I attempt to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. In this episode of Choosing Leadership, Sumit Gupta sits down with entrepreneur and leader Lokendra Tomar for a raw conversation about ambition, pressure, success, and what it actually takes to build a meaningful life while growing businesses. From navigating career pivots and scaling companies to making hard decisions during COVID, Lokendra shares the unseen emotional weight that leaders carry behind the scenes. This conversation will challenge the way you think about achievement, especially if you’ve ever felt trapped by expectations, comparison, or the pressure to constantly prove yourself. You’ll walk away with practical insights on trust, delegation, resilience, and building an internal anchor strong enough to withstand uncertainty and chaos. If you’re a founder, executive, or ambitious leader trying to grow without losing yourself in the process, this episode will hit close to home. You can find Lokendra Tomar at the links below https://www.linkedin.com/in/lokendratomar/ In the interview, Lokendra shares “Leadership gets dangerous when your self-worth becomes dependent on repeating your last success.”“Most people chase external validation. Real leaders build a life they actually enjoy living.”“The freedom to choose your path matters more than the prestige attached to it.”“Growth doesn’t come from comfort. It comes from stepping into uncertainty before you feel ready.”“A strong business means nothing if you lose yourself trying to build it.”“In moments of crisis, people don’t need perfection from leaders — they need honesty.”“The higher you climb, the more important trust and delegation become.”“Success without an internal anchor will eventually leave you exhausted, disconnected, and empty.”“The best leaders stop proving themselves and start multiplying impact through others.”“Leadership begins the moment you stop living by society’s definition of success and start defining it for yourself.”

    32 min
  3. Leadership Journeys [284] - Mark Coscarello - "Fulfillment comes from who you build with, not where you work"

    May 18

    Leadership Journeys [284] - Mark Coscarello - "Fulfillment comes from who you build with, not where you work"

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, I attempt to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. Most leaders chase success—but still feel something is missing. In this episode, Sumit Gupta sits down with Mark Coscarello to unpack why fulfilment in leadership has less to do with titles and money and everything to do with human connection. Mark shares his raw transition from corporate life to building a career rooted in trust, meaning, and aligned values—and what it really takes to discover your “why.” They dive into the uncomfortable realities of change, from redefining success to learning how to sell your value without losing your integrity. If you’re feeling stuck, disconnected, or ready to lead in a way that actually feels right, this conversation will challenge you to rethink what success means on your terms. You can find Mark Coscarello at the links below https://www.linkedin.com/in/markcoscarello/ https://www.markcoscarello.com/ In the interview, Mark shares “Leadership isn’t about position—it’s about the choices you make when no one is watching.”“Too many brilliant leaders stay stuck in survival mode instead of stepping into their full potential.”“Fulfilment doesn’t come from climbing the corporate ladder—it comes from meaningful human connection.”“Your ‘why’ isn’t something you find overnight—it’s something you uncover by paying attention to what actually matters to you.”“If the work you’re doing doesn’t energise you, it’s not a career—it’s a slow drain.”“Leaving the corporate world isn’t just a career shift—it’s an identity shift.”“Building a business is hard, but building it with people you trust makes it worth it.”“Transparency, integrity, and authenticity aren’t buzzwords—they’re the foundation of a life and business that actually work.”“Failure isn’t the opposite of success—it’s the training ground for it.”“Mediocrity is a choice—and so is excellence. The question is, which one are you practising daily?”

    37 min
  4. Leadership Journeys [283] - Katie Tamblin - " Very big egos often hide very fragile people"

    May 11

    Leadership Journeys [283] - Katie Tamblin - " Very big egos often hide very fragile people"

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, I attempt to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. What if the biggest thing holding you back as a leader isn’t strategy—but how you relate to people? In this episode, Katie Tamblin breaks down what it really takes to lead through uncertainty, build trust, and create teams that actually thrive. She shares hard-earned lessons on navigating change, managing emotions under pressure, and why curiosity might be your most underrated leadership skill. You’ll hear a refreshing take on success—one that prioritizes peace, authenticity, and long-term impact over ego and short-term wins. If you’re tired of surface-level leadership advice and ready to lead in a way that actually works, this conversation will challenge how you think—and how you show up. You can find Katie Tamblin at the links below https://www.linkedin.com/in/katietamblin/katietamblin.com In the interview, Katie shares Leadership isn’t a fixed path—it’s a series of transformations driven by curiosity and a willingness to change.The hardest transitions in leadership aren’t about skills—they’re about trust, relationships, and team dynamics.Great leaders don’t control everything—they build trust, delegate, and let people take ownership.Success isn’t just performance—it’s creating a sense of peace in how you and your team operate.Ego and righteousness often show up together—real leadership is choosing collaboration over being right.Emotional mastery isn’t optional in leadership—it’s the foundation for stability in chaotic environments.Curiosity is a leader’s greatest advantage—it keeps you learning, adapting, and open to better solutions.Growth will challenge your identity—not just your ability—and that’s where real development happens.Non-toxic workplaces don’t happen by accident—they’re built through conscious, values-driven leadership.Leadership isn’t about perfection—it’s about authenticity, learning as you go, and creating space for others to thrive.

    45 min
  5. Leadership Journeys [282] - Bob van Luijt - "Starting early compounds everything."

    Apr 28

    Leadership Journeys [282] - Bob van Luijt - "Starting early compounds everything."

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, I attempt to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. What does it really take to lead when everything in you wants to hold on tighter? In this episode, Bob van Luijt shares the unexpected journey from music to building a cutting-edge tech company—and why that path gave him an edge most leaders overlook. You’ll hear a raw take on letting go of control, building trust at scale, and leading without losing what makes you unique. If you’ve ever felt stuck in the weeds or unsure how to grow without breaking your culture, this conversation will challenge you. It’s an honest, refreshing look at leadership as a choice—and what becomes possible when you actually make it. You can find Bob van Luijt at the links below https://www.linkedin.com/in/bobvanluijt/ bob@weaviate.io.  In the interview, Bob shares “Leadership isn’t something you stumble into—it’s a choice you make, especially when it’s uncomfortable.”  “Most leaders are stuck in daily firefighting, but real impact begins the moment you decide to step out of it.”  “Your background doesn’t define your ceiling—sometimes the most unconventional paths create the most innovative leaders.”  “Discipline from one world can become your unfair advantage in another.”  “As your company grows, your job is to let go—not hold on tighter.”  “Trust isn’t just a leadership trait; it’s the foundation for innovation to exist.”  “Standing out is powerful—but only when it’s grounded in purpose, not ego.”  “Technology should amplify human potential, not replace it.”  “AI can scale efficiency, but it can’t replace genuine human connection.”  “The values you refuse to compromise on will define the company you build—and the leader you become.”

    33 min
  6. Leadership Journeys [281] - Kishan Ananthram - “Give more than you take and never forget where you came from.”

    Apr 20

    Leadership Journeys [281] - Kishan Ananthram - “Give more than you take and never forget where you came from.”

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, I attempt to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. What does it really take to build something meaningful that lasts for decades? In this episode of Choosing Leadership, Sumit Gupta sits down with Kishan Ananthram to unpack the mindset, values, and courage required to lead through uncertainty. Kishan shares hard-won lessons from a 30-year entrepreneurial journey—from choosing people over profit, to letting go of control so others can rise. If you are navigating growth, pressure, or the fear of making the wrong call, this conversation will challenge you to lead with more conviction, clarity, and heart. It is a powerful reminder that great leadership is not about playing safe—it is about choosing what matters most, even when it is uncomfortable. You can find Kishan Ananthram at the links below https://www.linkedin.com/in/kishanananthram/kishan.ananthram@ionidea.com  In the interview, Kishan shares “Leadership is not about the title you hold—it’s about the choices you make when comfort and courage collide.”“My father taught me two things: always aim for the top, and in every relationship, give more than you take.”“Building a business is not just about profit; it’s about creating something that people can trust with their future.”“There were moments I could have walked away with the money, but real leadership meant staying—for the sake of the people who built this with me.”“In difficult times, your values are no longer theory. They become the standard by which every decision is made.”“Growth begins the moment you stop treating the business like your possession and start building it as a shared legacy.”“Bringing in partners was not about giving up control—it was about multiplying possibilities.”“The real purpose of success is not accumulation; it is contribution to something greater than yourself.”“Leadership without inner work is incomplete. The deeper you understand yourself, the more responsibly you can lead others.”“Comfort is the enemy of greatness. If you want an extraordinary life, you have to be willing to choose discomfort in service of something bigger.”

    32 min
  7. Leadership Journeys [280] - Kunal Thakker - “Entrepreneurship gives you freedom but it quietly takes your presence.”

    Apr 14

    Leadership Journeys [280] - Kunal Thakker - “Entrepreneurship gives you freedom but it quietly takes your presence.”

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. What does it really take to walk away from a “safe” career and build something that changes an entire industry? In this conversation, Kunal Thakker shares the raw, unfiltered reality of leaving banking to reinvent dentistry—and why fear was actually his greatest advantage. You’ll get a behind-the-scenes look at the mental load of entrepreneurship, the sacrifices no one talks about, and how to stay grounded while scaling fast. Kunal also breaks down how he’s built a culture-first company in a highly technical field—and why that’s been his real edge. If you’re navigating growth, uncertainty, or big leadership decisions, this episode will challenge how you think and remind you what’s actually worth building. You can find Kunal Thakker at the links below https://www.linkedin.com/in/toothclub/https://www.toothclub.co.uk/In the interview, Kunal shares “Sometimes the biggest industry disruptors are the ones who start as outsiders.”  “Fear didn’t stop him—it became the reason he built something better.”  “Leaving a stable career isn’t reckless when you’re building something that actually matters.”  “Entrepreneurship gives you freedom—but it also rents space in your mind 24/7.”  “You can be with your family physically and still be miles away mentally—that’s the hidden cost of building something big.”  “Scaling a business is easy compared to preserving its culture.”  “Culture isn’t a department—it’s the foundation everything else stands on.”  “Great leadership is a constant balance between vision and adaptation.”  “If you’re not open to feedback, you’re not serious about growth.”  “The future belongs to those willing to rethink even the most traditional industries.”

    30 min
  8. Leadership Journeys [279] - Ron Rubin - “There’s gold in your backyard - if you’re willing to dig deep enough.”

    Apr 6

    Leadership Journeys [279] - Ron Rubin - “There’s gold in your backyard - if you’re willing to dig deep enough.”

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. What does it really take to hold onto a dream for 40 years—and actually bring it to life? In this conversation, Ron Rubin shares hard-earned lessons on patience, succession, and making bold decisions without losing your footing. You’ll hear how great leaders balance risk with wisdom, let go at the right time, and build businesses that last beyond them. More importantly, this episode challenges you to stop chasing distant opportunities and start recognising the “gold” already within your reach. If you’re navigating growth, transition, or uncertainty, this one will hit closer to home than you expect. You can find Ron Rubin at the links below https://www.linkedin.com/in/ronrubin/ ron@goldenyourbackyard.comIn the interview, Ron shares “Dreams don’t expire—they just wait for the person patient enough to build them.”“What looks like a long delay is often just the time required to do something meaningful.”“The best business advice I ever received was simple: stay debt-free and sleep well at night.”“Succession isn’t about stepping away—it’s about setting someone else up to win.”“If you don’t have a plan to let go, you don’t have a leadership strategy—you have control issues.”“Most people chase opportunity in distant places, while ignoring the gold sitting in their own backyard.”“The real lessons of leadership aren’t taught in classrooms—they’re earned through decisions, risks, and consequences.”“Great leaders don’t avoid risk—they understand it, respect it, and move anyway.”“Innovation matters, but never at the expense of the human touch that built your business in the first place.”“Success means very little if you’re not lifting others as you climb.”

    23 min
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About

As a leader, you are always making choices. Even when you think you have no choice. And if you are unable to make a decision, you are choosing to stay in a state of indecision. The only question is - are your choices taking you where you want to go? I am Sumit Gupta, and this is "Choosing Leadership" - a podcast for high performers with big dreams - who know deep inside that there is more. This is a podcast for people who know they are more powerful than the level they are currently playing. I have spent a long time feeling powerless, and that is why I see where you are powerful even when you cannot. I dare to say what most people would not. I dare to speak to the "tremendous power" which you already have rather than what you believe are your strengths and limitations. This podcast is called "choosing leadership" - because that is what leadership is - a choice. The choice to step into the unknown. The choice to see fear as a friend. The choice to take courageous action rather than waiting for readiness. Join Sumit in exploring this question when it comes to your leadership. In each moment of life, are you Deploying Yourself or not? In each moment of life, are you Choosing Leadership or not?

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