Choosing Leadership with Sumit Gupta

Hosted by Sumit Gupta

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337

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Oct 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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October 21, 202632 min

Leadership Journeys [299] - Brigitta Lops - "Make soft skills as natural as riding a bike."

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 soft skills were as natural as riding a bike? Brigitta Lops owns two behavior-change companies (Job Training, founded in 1991, and Hello New You), is a mother of two, and bought into the company through a management buyout. In this conversation she talks about the hardest leadership lesson she has learned: knowing when to let go, whether of a child, an employee or your own role as the person who fixes everything. We talk about why ownership is easy to speak about and hard to practice, how her company pivoted its whole classroom business to virtual in 10 days when COVID hit, why she hired a managing director (and why she wishes she had done it sooner), what it was like to lead as a young female entrepreneur, and why an AI coach in your pocket can only help if you connect the practice to real life. Brigitta ends with the mission she wants to own for the next decade, the challenge of listening instead of spreading the word, and a simple rule she lives by: choose growth over comfort. You can find Brigitta at the links below LinkedIn: https://www.linkedin.com/in/brigitta-lops-bab4423/ In the interview, Brigitta shares "I really want to make soft skills as natural as riding a bike." "When you build a company, it's linked to your identity, to your ego." "Ownership is easy to talk about, but when the going gets tough, that's when you can really show what ownership means." "You can be assertive and strong and opinionated, and be kind as well." "You don't have to edit yourself to fit in." "You can practice until your face gets blue." "We really need the struggle of live interaction to learn about that live interaction." "I try to choose growth over comfort."

October 14, 202631 min

Leadership Journeys [298] - Paulo De Tarso - "Hospitality and the Art of Leadership with Paulo De Tarso"

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 secret to a business that lasts is not a clever strategy, but treating hospitality as a way of serving people, your guests and your staff alike? Paulo De Tarso opened his first coffee shop in New York at 15 or 16, started again from the bottom as a dishwasher and worked his way up through the ranks of the restaurant world. He fell in love with hospitality because of how loyal people are when you look after them well. Years later he opened Margot in London, with 72 people on the payroll and a restaurant that was full at night and empty at lunch. Paulo and Sumit explore what he did when the pressure hit: how he and his partner went door to door, invited neighbours and concierges in for lunch, and let word of mouth do the work. They talk about failure as part of the journey, why curiosity matters more than being right, and why bad service is so often a leadership problem rather than a people problem. They also go into where technology helps and where it does not, why guests still need to be greeted and acknowledged by a human, and what Paulo expects from himself and his team as non-negotiables. He makes the case for mentoring, for training people properly and for giving young people leaders worth following. You can find Paulo at the links below LinkedIn: https://www.linkedin.com/in/paulo-de-tarso-65734527/ Instagram: @paulodetarso24 In the interview, Paulo shares "Failure is part of your journey. If life was happy every day, you wouldn't be learning anything." "Don't be afraid of asking a question. You get it wrong, but now you know, and now you can move on." "I still believe that word of mouth is the most powerful PR there is." "When you're truly successful, I believe that's when your local community is coming after you." "If your staff don't have passion, maybe your recruitment needs to improve. Maybe it is your fault that you're not training and motivating people well enough." "In the restaurant world, we are only as good as our last service." "I used to say to my team, 'You give me 50%, I'll give you 50%, and together we're a good team.'" "You need to be served by a human. You need to be acknowledged by a human." "There are a lot of wonderful young people out there who are willing to learn. They don't go into hospitality because they've had so many poor leaders." "If every restaurant and every hotel is educating and looking after their staff, the world will be a better place."

October 9, 202638 min

Leadership Journeys [297] - Oliver Pickup - "With AI, I want humans to be the carpenter rather than the nail."

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 the first rung of the career ladder when AI takes over the entry-level work? In this conversation, Oliver Pickup, a journalist of more than 20 years who now calls himself a human work evolution storyteller, shares how the launch of ChatGPT gave him what he calls FOBO, the fear of becoming obsolete, and how it pushed him out of his comfort zone and onto the speaking stage. Oliver and Sumit explore why he sees three tribes (AI martyrs, AI zealots and AI agnostics), why he treats AI as a smart intern while keeping the creative process and the end product his own, and why a world drowning in AI slop will reward lived experience, personality and detail. For leaders, Oliver raises a pointed warning about the vanishing first rung: if companies hand all the entry-level work to AI and stop bringing in young talent, what will their garden look like in five years? He also explains why people need a vision and proper training before you hand them the keys to a Formula 1 car. Underneath it all is a family thread: how becoming a father reset his values, why he builds Friday afternoons around watching his son play rugby, and why reading the bedtime story together still counts, even when AI can write one in a blink. You can find Oliver Pickup at the links below https://www.linkedin.com/in/ojpickup/ https://oliverpickup.com In the interview, Oliver shares “I want humans to be the carpenter rather than the nail at the other end of the hammer.” “AI is making many of us a hamster going faster on a faster wheel. The more tech you throw at something, the busier people are.” “There are AI martyrs who think AI will take their job, AI zealots who defer to it for everything, and AI agnostics who don't fear it and don't worship it. They see it as a tool.” “I use AI as a smart intern to help with the legwork, but the creative process and the end product are all mine.” “Generative AI is the average of the average, so it's clear to see when something isn't up to the standard a human would produce.” “The heart skills, the seven C's, are collaboration, compassion, communication, courage, critical thinking, creativity and curiosity. They matter more as the machines get stronger.” “I just don't think we should be so ready to give all the keys to the castle to AI.” “We need that lived experience. We need that messiness. We need that friction to really understand a problem.” “If you don't water the garden with young talent, in five years' time you're looking at a garden that is completely barren.” “AI can write a bedtime story in a blink, but it's taking the time to read it with her that truly counts in the end.”

September 3, 202648 min

Leadership Journeys [296] - Sree Varma - "Success means nothing if you lose your family along the way."

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 success stops being about building a bigger business and starts being about building a life that actually matters? In this powerful conversation, Sree Varma opens up about his journey from arriving in the UK with just £150 to building successful ventures while navigating adversity, self-doubt, and a deeply personal purpose. He shares why great leadership isn’t about working harder, but about building strong systems, developing capable leaders, and creating the freedom to focus on what truly matters. If you’re a founder or leader who feels trapped in the business you built, this conversation offers a powerful reminder that your company should not need your constant presence to succeed. More importantly, Sree and Sumit explore what it means to turn success into service and build a legacy that creates impact far beyond yourself. You can find Sree Varma at the links below https://www.linkedin.com/in/sreevarma/ In the interview, Sree shares “Leadership is not about the title you hold; it’s about the choices you make and the impact you create.” “True success is not just about building businesses. It’s about using what you build to create a better world for others.” “Sometimes, life changes your definition of success. What once was about achievement can become about purpose, contribution, and legacy.” “You don’t build a great company by working 20 hours a day forever. You build it by creating systems and developing people who can lead without you.” “Delegation isn’t about doing less. It’s about creating the capacity to contribute at a much higher level.” “The goal isn’t to make yourself indispensable. The goal is to build something that can thrive even when you step away.” “Imposter syndrome doesn’t always disappear with success. Sometimes, the more you achieve, the more you question whether you deserve it.” “Leadership requires balancing ambition with contentment—always growing while learning to appreciate how far you’ve already come.” “Your greatest achievement may not be what you build for yourself, but what your success makes possible for other people.” “Leadership is a choice: a choice to dream bigger, serve others, and leave a legacy that extends far beyond your own success.”

August 25, 202633 min

Leadership Journeys [295] - Sarah Webster - "Train your mind to outlast your excuses."

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 your ability, but the limits you’ve convinced yourself are real? In this inspiring conversation, world-record ultrarunner Sarah Webster shares how running 278 kilometres in 24 hours taught her lessons about resilience, discipline, adaptability, and discovering what she is truly capable of. Her journey is a powerful reminder that extraordinary results rarely come from comfort—they come from being willing to keep going, adjust the plan, and push beyond what you thought was possible. Whether you’re leading a team, building a business, or simply trying to achieve something that matters deeply to you, Sarah’s story will challenge you to rethink your own limits. Tune in for a candid, energising conversation about perseverance, leadership, and what becomes possible when you stop negotiating with your potential. You can find Sarah Webster at the links below https://www.instagram.com/sarah.webster.948/ In the interview, Sarah shares “You realise you are capable of far more than you ever thought you could do.” “The biggest limits we face are often the ones we create in our own minds.” “Leadership, like endurance running, is about pushing beyond the boundaries you thought were fixed.” “Success isn’t just reaching the peak; it’s having the discipline to keep climbing when the journey gets hard.” “Planning, discipline, and flexibility are just as important as physical strength when you’re pursuing something extraordinary.” “You don’t have to follow the conventional path to achieve an unconventional result.” “There is always something to learn, whether the race went exactly as planned or completely off course.” “The moment you challenge your own limits is the moment you discover what you’re truly capable of.” “Find what you love, practice relentlessly, and allow yourself to discover how far you can really go.” “Comfort is the enemy of greatness. Mediocrity is a choice, and so is excellence.”

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."

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