Choosing Leadership with Sumit Gupta
Choosing Leadership with Sumit Gupta

Choosing Leadership with Sumit Gupta

Sumit Gupta

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Episodes

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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?

Recent Episodes

Leadership Journeys [278] - Lindsay Nahmiache - "Growth feels like discomfort. Comfort feels like stagnation."
MAR 24, 2026
Leadership Journeys [278] - Lindsay Nahmiache - "Growth feels like discomfort. Comfort feels like stagnation."
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.Growth doesn’t feel like confidence—it feels like discomfort, doubt, and stepping into rooms where you’re not the smartest person yet. In this episode of Choosing Leadership, Sumit Gupta sits down with Lindsay Nahmiache to unpack what it really takes to grow when comfort is no longer an option. They dive into how embracing uncertainty, building systems, and telling better stories can unlock exponential growth in business and life. If you’re leading a team, building something ambitious, or feeling stuck at your current level, this conversation will challenge the way you think about progress. Expect real talk, practical insights, and a nudge to stop waiting until you feel ready—because leadership starts the moment you choose to move anyway.You can find Lindsay Nahmiache at the links belowhttps://www.linkedin.com/in/lindsaynahmiache/https://jiveprdigital.com/In the interview, Lindsay shares“If growth feels comfortable, you’re probably not growing at all.”“Discomfort isn’t a sign you’re failing—it’s proof you’re evolving.”“Entrepreneurship is learning to feel at home in the unknown.”“Every breakthrough I’ve had came from stepping into situations I couldn’t control.”“Storytelling isn’t marketing—it’s how people decide whether to trust you.”“You don’t stumble into opportunity; you recognise it because you’re paying attention.”“The edge of growth is uncomfortable, and that’s exactly where leaders are built.”“Systems don’t limit freedom—they create it.”“Not everyone is meant to want more, and that’s okay. Leadership is choosing to want more anyway.”“Authenticity isn’t a brand strategy—it’s how you stop lying to yourself about who you’re becoming.”
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28 MIN
Leadership Journeys [277] - Joe Seddon - "Be delusional about the mission. Be ruthless about the execution."
MAR 17, 2026
Leadership Journeys [277] - Joe Seddon - "Be delusional about the mission. Be ruthless about the execution."
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 build something meaningful when you have no money, no network, and no permission? In this episode of Choosing Leadership, host Sumit Gupta sits down with Joe Seddon, who built Zero Gravity from his student bedroom with his last £200 and a healthy dose of bold belief. They unpack the uncomfortable truths about execution, rejection, and why a little “delusion” might be the edge most leaders are missing. You’ll hear how to cut through distraction, build a culture of accountability, and stay grounded while chasing ambitious goals. If you’ve been playing it safe, this conversation will challenge you to step up, think bigger, and lead with courage—starting now.You can find Joe Seddon at the links belowhttps://www.linkedin.com/in/joeseddon/https://www.zerogravity.co.uk/In the interview, Joe shares“Talent is everywhere, but opportunity is not. Our job as leaders is to close that gap.”“Sometimes you have to be a little delusional to build something meaningful—especially when you don’t have money, connections, or permission.”“Naivety isn’t always weakness; sometimes it’s the fuel that keeps you moving when the odds say stop.”“If you wait until you feel ready, you’ll never start. Real leaders move before confidence shows up.”“Cold-calling, handwritten letters, uncomfortable asks—that’s what execution looks like when you have no leverage.”“In a world competing for attention, leadership means helping people invest their time in their future, not just their entertainment.”“Culture isn’t your values on a wall—it’s whether people actually do what they say they’ll do.”“Standing up straight means saying what you intend to do and doing what you said you would do.”“Growth doesn’t come from adding more to your day; it comes from changing the context you operate in.”“Comfort is the enemy of greatness—choosing leadership means choosing discomfort on purpose.”
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31 MIN
Leadership Journeys [276] - Kaihan Krippendorff - "Most companies lack the space to talk about impossible ideas"
MAR 9, 2026
Leadership Journeys [276] - Kaihan Krippendorff - "Most companies lack the space to talk about impossible ideas"
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 if the ideas you’ve been quietly dismissing are the very ones that could change everything? In this episode of Choosing Leadership, Kaihan Krippendorff joins Sumit Gupta to unpack why most leaders struggle to create space for bold thinking—and how to break out of safe, stale patterns. You’ll learn how courage, language, and choice shape the future of your leadership more than any strategy deck ever will. This conversation challenges you to stop predicting outcomes and start committing to what you want to create, even when it feels uncomfortable. If you’ve been playing it safe while hoping for extraordinary results, this episode will shake you awake—in the best way.You can find Kaihan Krippendorff at the links belowhttps://www.linkedin.com/in/kaihankrippendorff/https://outthinker.com/In the interview, Kaihan shares“Most companies don’t fail because they lack ideas; they fail because they don’t create space for impossible ones.”“Innovation begins the moment you stop borrowing other people’s beliefs and start trusting your own logic.”“Courage isn’t loud confidence—it’s the quiet decision to bet on your thinking when the world disagrees.”“If your language can’t imagine a new future, your strategy won’t create one.”“Leaders don’t just predict outcomes—they commit to creating them.”“Without choice, there is no accountability. Leadership begins the moment you choose.”“The fourth option appears only after you’ve exhausted the obvious three.”“Breakthroughs don’t come from better answers; they come from better questions.”“Comfort is efficient, but it’s also the enemy of greatness.”“Leadership isn’t about doing more—it’s about choosing what truly matters and committing to it boldly.”
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25 MIN
Leadership Journeys [275] - Janardan Dalmia - "Success has many fathers and failure is an orphan"
MAR 3, 2026
Leadership Journeys [275] - Janardan Dalmia - "Success has many fathers and failure is an orphan"
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 certainty and choose leadership in the unknown?In this episode of Choosing Leadership, host Sumit Gupta sits down with Janardan Dalmia to unpack his journey from Wall Street banking to building Trukkin in one of the world’s most complex logistics markets.JD shares the unglamorous truths of entrepreneurship—unlearning old mindsets, navigating uncertainty, and building resilience when the playbook no longer exists.This conversation is a powerful reminder that leadership isn’t about linear growth or perfect balance, but about endurance, self-awareness, and choosing courage over comfort.If you’re a leader facing big decisions, internal resistance, or the fear of starting over, this episode will challenge you to raise your bar and play a longer, bolder game.You can find Janardan Dalmia at the links belowhttps://www.linkedin.com/in/jdalmia/ [email protected]. In the interview, Janardan shares“Leadership isn’t a title you earn once — it’s a choice you make every day.”“Leaving Wall Street didn’t make me brave — staying uncomfortable did.”“Entrepreneurship isn’t a straight line. It’s a messy, non-linear journey, and that’s the point.”“You don’t rise in business by avoiding failure — you rise by learning to recover faster.”“Success is temporary. So is failure. What lasts is who you become through both.”“Unlearning the banker mindset was harder than learning how to build a startup.”“Real leadership is about endurance — staying in the game when the excitement wears off.”“You can’t professionalise chaos without first learning to operate inside it.”“Work-life balance isn’t about equal hours — it’s about protecting your energy.”“Growth isn’t about doing more. It’s about becoming more.”
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24 MIN
Leadership Journeys [274] - Christopher Graham - “Transformation starts when the founder steps back and the team steps up.”
FEB 23, 2026
Leadership Journeys [274] - Christopher Graham - “Transformation starts when the founder steps back and the team steps up.”
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.This episode is a masterclass in what happens when a leader stops reacting and starts thinking. Christopher Graham shares how stepping back from daily chaos unlocked scale, clarity, and a completely new way of leading at Crown Capital. You’ll hear why micromanagement feels productive but quietly kills growth—and what to do instead. The conversation dives into curiosity, mental space, and building businesses that don’t depend on the founder for every decision. If you’re tired of being the bottleneck in your own leadership, this episode will challenge how you run your company and yourself.You can find Christopher Graham at the links belowhttps://www.linkedin.com/in/christophertgraham25/https://crown-inv.com/In the interview, Christopher shares“Leadership changed for me the moment I stopped reacting to daily problems and started blocking time to actually think.”“Growth didn’t come from working harder—it came from creating mental space to see what was possible.”“My move into private equity wasn’t planned; it emerged by saying yes to opportunities my clients put in front of me.”“Ego convinces founders they need to touch everything. Scale demands the opposite.”“Real leadership begins when the business can operate and grow without the founder being in every decision.”“Micromanagement feels productive, but it quietly suffocates innovation and limits scale.”“Mapping a business forces clarity—it exposes inefficiencies you can’t see when you’re too close to the work.”“When leadership teams are involved in diagnosing problems, change stops being forced and starts becoming owned.”“Curiosity is a competitive advantage—it keeps leaders adaptable in environments that won’t slow down for them.”“The future belongs to leaders who can step back, challenge tradition, and build systems that outlive them.”
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28 MIN