Choosing Leadership with Sumit Gupta

Hosted by Sumit Gupta

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332

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Aug 2026

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About the show

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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August 17, 202641 min

Leadership Journeys [294] - Gaspar Rodriguez - "You don't need to become someone else to belong."

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 building a company had more in common with ultracycling than you ever imagined? In this powerful conversation, Gaspar Rodriguez, founder and CEO of Blue Road Academy, shares how resilience, belonging, and the willingness to keep moving forward have shaped both his leadership journey and his life. He opens up about navigating failure, making imperfect decisions, building a strong organisational culture, and turning personal adversity into purpose. For leaders facing uncertainty, setbacks, or the challenge of bringing different people together, Gaspar offers a refreshing reminder that you don’t have to conquer the entire journey at once—you simply need to take the next step. This is a conversation about choosing leadership, embracing the journey, and recognising just how much potential can emerge when people feel seen, valued, and empowered. You can find Gaspar Rodriguez at the links below https://www.linkedin.com/in/gaspar-rodriguez/ https://www.linkedin.com/company/blueroadacademy/ In the interview, Gaspar shares “Whether you’re building a company or cycling 500 kilometres, you don’t conquer the whole journey at once. You focus on the next step, the next challenge, and keep moving forward.” “The desire to belong is universal. No matter where we come from, we all want to feel that we matter and that we have a place.” “When you enter a new environment, your value doesn’t disappear. You bring your experiences, your perspective, and everything you’ve learned along the way.” “Leadership isn’t about making perfect decisions. It’s about making the best decision you can with the information and circumstances you have, then having the courage to learn from it.” “Sometimes the hardest experiences in life become the very things that build our resilience and reveal what we’re truly capable of.” “Refugees are often defined by what they’ve lost. We need to start seeing them for what they bring—their resilience, their experience, and their untapped potential.” “You don’t have to be the perfect manager to be a powerful leader. Leadership starts with having a clear purpose, a compelling vision, and the willingness to bring others along.” “Sustainable growth happens when you stop trying to create the vision alone and empower the people around you to shape it with you.” “Real inclusion isn’t simply giving people a place at the table. It’s recognising the contribution they are capable of making once they’re there.” “Life isn’t a series of tasks to be conquered. It’s a journey to be experienced, and every step forward is a testament to your resilience and potential.”

August 4, 202642 min

Leadership Journeys [293] - James Tattersfield - "Confidence is built by making mistakes repeatedly."

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. Leadership isn't about having all the answers, it's about having the courage to keep growing. In this conversation, James Tattersfield, CEO of Polar Insight, shares how curiosity, failure, observation, and even mountaineering have shaped the leader he is today. You'll discover why confidence is earned through experience, how to make better decisions under pressure, and why staying close to the people you serve is one of the greatest competitive advantages a leader can have. Whether you're leading a startup, a global organisation, or simply trying to become a better leader, this episode offers practical insights you can put into action immediately. If you're ready to lead with greater clarity, resilience, and authenticity, this is an episode you won't want to miss. You can find James Tattersfield at the links below https://www.linkedin.com/in/jamestattersfield/ https://polarinsight.com/ In the interview, James shares “Confidence isn’t something you’re born with. It’s built by stepping into the unknown, making mistakes, and doing it again.” “Observation is a leadership superpower. The more you understand people before you act, the better your decisions become.” “The best leaders don’t rush to prove themselves. They take time to observe, understand, and then act with intention.” “Real confidence comes from experience—not from getting everything right, but from learning through failure.” “Leadership isn’t about having all the answers. It’s about making decisions that align with your values, even when they’re difficult.” “The mountains teach what boardrooms often can’t: perspective, resilience, and the ability to stay grounded under pressure.” “Personal growth isn’t separate from professional success. The more you grow as a person, the better you lead others.” “Great organisations are built on stakeholder proximity—staying close enough to customers, employees, and partners to make better decisions.” “The strongest leaders combine data with intuition, balancing evidence, experience, and authenticity when making decisions.” “Choosing leadership means choosing growth over comfort, courage over certainty, and purpose over playing small.”

July 28, 202652 min

Leadership Journeys [292] - Eduard Schaepman - "Reputation builds relationships. Relationships build business."

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 key to growing your business isn't a better strategy, but stronger relationships? In this episode of Choosing Leadership, Eduard Schaepman shares how building a trusted reputation, cultivating authentic communities, and embracing change have shaped his journey as an entrepreneur and CEO. Together with host Sumit Gupta, they explore why the future of leadership depends on human connection, even as AI transforms the way we work. You'll also hear practical insights on navigating uncertainty, leading with transparency, and creating environments where people and businesses can thrive. If you're looking to build lasting impact as a leader, this conversation will challenge your thinking and leave you with actionable ideas to put into practice. You can find Eduard Schaepman at the links below https://www.linkedin.com/in/eduardschaepman/ https://theexperiencenet.com/ In the interview, Eduard shares “Your reputation opens doors, but your relationships determine how far you’ll go.” “The strongest businesses aren’t built on transactions—they’re built on genuine communities.” “Leadership begins when you stop accepting the status quo and start creating a better future.” “Community isn’t about sharing the same space; it’s about sharing trust, purpose, and honest conversations.” “The best entrepreneurs never stop learning, adapting, and embracing change.” “Innovation happens faster when leaders listen openly, communicate transparently, and act decisively.” “Governments and organisations create better outcomes when they learn from the entrepreneurs solving real-world problems.” “AI is a powerful tool for improving efficiency, but it can never replace human judgment, empathy, or meaningful relationships.” “When technology handles repetitive work, people have more time to build the connections that truly matter.” “A lasting leadership legacy is built through reputation, strengthened by relationships, and sustained by the communities you serve.”

July 20, 202637 min

Leadership Journeys [291] - Laurens van de Vijver - "The right company doesn't just grow revenue. It grows impact."

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 leadership decision you'll ever make is choosing what kind of company you're building? In this episode of Choosing Leadership, Sumit Gupta sits down with Laurens van de Vijver, CEO of MyWheels, to explore how purpose, long-term thinking, and courageous decision-making can create businesses that leave a lasting impact on society. Together, they discuss the tension between short-term results and sustainable growth, how AI can strengthen rather than replace human leadership, and why great leaders never lose sight of the bigger picture. If you're navigating difficult decisions, leading through change, or wondering how to grow your business without compromising your values, this conversation is packed with practical insights. Tune in and discover how choosing the right mission can transform not only your organization but the world around it. You can find Laurens van de Vijver at the links below https://www.linkedin.com/in/laurens-van-de-vijver-0a94ab/ In the interview, Laurens shares "The most fulfilling work happens when your personal values align with your company's mission." "Great companies don't just generate profit—they create lasting value for society." "Leadership means choosing long-term impact over short-term convenience, even when it's harder." "Real innovation doesn't replace human judgment; it amplifies it." "The best leaders combine intuition, experience, and technology to navigate an uncertain future." "Building a successful business isn't just about growing bigger—it's about making a meaningful difference." "Systemic change happens when businesses stop solving symptoms and start addressing root causes." "A company's greatest legacy isn't its revenue—it's the positive impact it leaves on people and society." "The future belongs to organisations that collaborate to solve society's biggest challenges, not just compete for market share." "Choosing leadership means having the courage to build a business that makes the world better, not just more profitable."

July 13, 202626 min

Leadership Journeys [290] - Ajeya Raj - "Your real power is your mind, everything else can be replaced."

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 happens to leadership when life removes every assumption you had about control, identity, and ability? In this episode, Ajeya Raj shares a story that will challenge how you think about resilience, purpose, and what it really means to lead yourself when circumstances change overnight. After a life-altering accident left him paralysed below the neck, Ajeya made a choice most people never face: to expand his definition of possibility instead of shrinking his life. He takes us through the mindset shifts that helped him move beyond limitation, from aspiring civil service officer to international athlete and Paralympic hopeful. If you are navigating uncertainty, leading through pressure, or questioning what’s still possible, this conversation will stretch your perspective most practically and humanly. You can find Ajeya Raj at the links below https://www.linkedin.com/in/ajeya-raj-life-with-c4-249753213/ In the interview, Ajeya shares "The biggest disability is not in the body; it's in the belief that you cannot achieve something." "When life changed in an instant, I had two choices: focus on what I had lost or discover what I was still capable of becoming." "Your mind is your most powerful asset. When you strengthen your thinking, you strengthen your future." "Many people have functioning bodies but never use their full potential. True ability begins with the courage to act." "Resilience is not about avoiding challenges; it's about choosing to rise every time life knocks you down." "Sometimes life redirects us away from the dream we planned so we can discover a purpose far greater than we imagined." "Limitations become opportunities when you stop asking, 'Why me?' and start asking, 'What's possible now?'" "Faith, determination, and a positive mindset can take you places that physical strength alone never could." "Leadership begins when you stop waiting for circumstances to improve and start taking responsibility for your next step." "The human spirit is far more powerful than any obstacle. When you believe in yourself, extraordinary possibilities emerge."

July 6, 202638 min

Leadership Journeys [289] - Arthur Gopak - "Wisdom begins when you listen beyond yourself."

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 take to turn unexpected opportunities into a life and career beyond your wildest imagination? In this episode of Choosing Leadership, Arthur Gopak shares his remarkable journey from a shy teenage journalist interviewing world leaders to building successful businesses in media and wealth management. Together, Arthur and Sumit explore the power of trusting your intuition, embracing discomfort, and making courageous choices when the path ahead is uncertain. If you've ever felt stuck between playing it safe and pursuing a bigger vision, this conversation offers practical insights for navigating uncertainty and creating opportunities where others see obstacles. Tune in to discover why some of the most important leadership decisions begin with a simple willingness to say yes before you feel ready. You can find Arthur Gopak at the links below https://www.linkedin.com/in/agopak/ https://arthurgopak.com/ In the interview, Arthur shares "The opportunities that change your life rarely arrive when you feel ready. They arrive when you're willing to step beyond your comfort zone." "Leadership begins the moment you stop waiting for permission and start trusting your own judgment." "Listening to your gut isn't about ignoring logic; it's about having the courage to follow a path that others may not understand." "Credibility is built when expertise meets visibility and consistently creates value for others." "The biggest breakthroughs often come from saying yes to opportunities that initially feel intimidating." "Success isn't about getting every decision right. It's about learning quickly when your assumptions are wrong and adapting accordingly." "Great leaders don't follow the crowd; they develop the confidence to chart their own course." "Your background doesn't determine your future. The choices you make when opportunity appears do." "Comfort may feel safe, but growth lives on the other side of uncertainty." "Leadership is a choice to pursue excellence despite fear, resistance, and the temptation to settle for mediocrity."

June 29, 202647 min

Leadership Journeys [288] - Michelle Hill - "The quality of your life is the quality of your relationships."

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 take to lead through growth, uncertainty, and the constant pressure to have it all figured out? In this episode of Choosing Leadership, Sumit Gupta sits down with Michelle Hill, CEO of TLC, to explore her journey from a young woman passionate about social justice to leading a national organisation with an ambitious vision for change. Together, they unpack the realities of leadership, including self-doubt, imposter syndrome, scaling culture, and the importance of building genuine relationships in a divided world. Michelle shares hard-earned lessons on self-care, resilience, and staying true to your values while pursuing bold goals. If you're navigating leadership challenges, growing a team, or striving to create a greater impact, this conversation will leave you with practical insights and a renewed perspective on what leadership really requires. You can find Michelle Hill at the links below https://www.linkedin.com/in/michelle-hill-567495a8/ https://talklistenchange.org.uk/ In the interview, Michelle shares "Leadership begins when you stop waiting for permission and start making choices that align with the difference you want to make." "The strongest leaders understand that you cannot pour from an empty cup; self-care is not a luxury, it's a responsibility." "Growth is exciting, but scaling an organisation means protecting the culture that made it successful in the first place." "Authentic leadership isn't about having all the answers; it's about being honest enough to keep learning." "Some of the most important leadership decisions are also the loneliest, which is why supportive relationships matter." "Imposter syndrome doesn't disappear when you become a CEO; you simply learn how to keep moving forward despite it." "Healthy organisations are built on transparency, communication, and a genuine commitment to listening." "Curiosity and openness create space for meaningful conversations, especially in a world that often rewards division." "Real impact isn't measured by how big an organisation becomes, but by how many lives it can reach and transform." "A world filled with safe, healthy, and happy relationships doesn't happen by chance—it happens when leaders choose to make it possible."

June 22, 202648 min

Leadership Journeys [287] - Gerrit Sarens - "Great leaders know their strengths and their blind spots."

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 happens when someone walks away from a successful academic career to build something completely different? In this episode, Gerrit Sarens shares his journey from becoming the youngest professor at university to stepping into the uncertainty and excitement of entrepreneurship. Together, we explore what it takes to embrace risk, develop deep self-awareness, and lead beyond the limits of your comfort zone. Gerrit offers powerful insights on mentoring, personal growth, and why the best leaders are committed to understanding both their strengths and their blind spots. If you're facing a big leadership decision or wondering whether you're capable of more than your current path, this conversation will challenge you to think bigger and choose courage over certainty. You can find Gerrit Sarens at the links below https://www.linkedin.com/in/gerritsarens/ https://www.ambits.eu/ In the interview, Gerrit shares "Leadership is not a position you hold; it's a choice you make every day." "Growth begins the moment you step beyond the comfort of what you've already mastered." "Academia taught me how to think deeply; entrepreneurship taught me how to act boldly." "The transition from individual achievement to collective success is one of the most important leadership journeys." "The best leaders know their strengths, understand their blind spots, and stay curious enough to keep learning." "Entrepreneurship has a way of revealing who you really are when certainty disappears." "A great mentor doesn't give you answers; they help you see what you couldn't see on your own." "Every meaningful transformation starts with personal growth before it ever shows up in business results." "Big visions often feel uncomfortable to say out loud, but that's usually a sign they're worth pursuing." "When leaders become better human beings, they create better businesses, stronger communities, and a better society."

June 2, 202650 min

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.”

May 26, 202632 min

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.”