Leaders Who Coach™ PODCAST with Sehaam Cyrene

The Power of We: Leading with Responsibility, Credibility and Team Alignment 🎙️ with Jon Freedman

48 min · 30. mar. 2026
episode The Power of We: Leading with Responsibility, Credibility and Team Alignment 🎙️ with Jon Freedman cover

Description

What does it take to lead with clarity, credibility and responsibility in high-pressure environments? In this episode of the Leaders Who Coach™ Podcast, Sehaam Cyrene speaks with Jon Freedman, Fractional CTO and financial technology strategist, about what it really takes to build high-performing teams, create alignment and lead with impact in complex organisations. Jon shares insights from over 20 years in financial technology, working across investment banks and hedge funds, and scaling global teams in fast-paced, high-stakes environments.  This conversation explores how leaders can move beyond technical expertise and develop the communication, credibility and coaching skills needed to influence, align and grow teams effectively. Together, they explore: • Why responsibility (not ownership) is a powerful leadership mindset • How credibility is built through consistent behaviour over time • The importance of aligning teams around a clear “why” • Why technical expertise alone is not enough to differentiate yourself • How to handle strong opinions and disagreement in teams • The role of listening in effective leadership and decision-making • Why coaching is more effective than command-and-control leadership • Leading through ambiguity and communicating progress effectively • Scaling teams quickly while maintaining quality and cohesion • Why inclusive leadership (“we” not “I”) builds stronger teams This is a thoughtful and practical conversation about leadership maturity, communication and building teams that perform under pressure while remaining aligned and collaborative. If this episode resonates with you, you can connect with Jon here:  👉 Jon Freedman on LinkedIn [https://www.linkedin.com/in/jonfreedman/] 🎧 Listen & Follow Sehaam:  LinkedIn: https://www.linkedin.com/in/sehaam/ [https://www.linkedin.com/in/sehaam/] YouTube: https://www.youtube.com/@SehaamCyrene [https://www.youtube.com/@SehaamCyrene] Instagram: https://www.instagram.com/sehaam.cyrene/ [https://www.instagram.com/sehaam.cyrene/] TikTok: https://tiktok.com/leaderswhocoach [https://tiktok.com/leaderswhocoach] 📲 Download the Leaders Who Coach™ App and complete the Foundation Module free. 00:00 – Introduction to the episode 00:28 – Meet Jon Freedman and his background 02:47 – From Morgan Stanley to hedge funds: career journey 05:13 – Leadership vs management: showing up early as a leader 07:25 – Responsibility, credibility and trust in teams 09:39 – Differentiating beyond technical skills 12:00 – Aligning teams around the “why” 14:24 – Practising soft skills under pressure 15:44 – Communicating mission and building alignment 18:10 – Coaching vs command-and-control leadership 20:12 – Influencing decisions through coaching conversations 23:45 – Handling strong opinions and disagreement 25:51 – The importance of listening as a leader 27:37 – Building respect and avoiding “us vs them” 31:17 – Leading humans, not systems 33:45 – Balancing clarity, direction and flexibility 35:43 – Credibility and direct communication 38:03 – Leading through ambiguity and uncertainty 41:54 – Managing expectations and communicating progress 43:32 – Collaboration, transparency and trust 45:37 – Scaling a team from 7 to 90 people 48:12 – Hiring at speed: trade-offs and decision-making 52:32 – Building a high-performing and diverse team 55:51 – A defining leadership lesson: giving credit to others 58:05 – The power of “we” in leadership 01:00:26 – Final reflections

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14 episodes

episode Navigating AI's Rapid Evolution with Darcy Peters artwork

Navigating AI's Rapid Evolution with Darcy Peters

What does it take to lead with clarity, humility and human connection while navigating the rapid rise of AI? In this episode of the Leaders Who Coach™ Podcast, Sehaam Cyrene [https://www.linkedin.com/in/sehaam/] speaks with Darcy Peters [https://www.linkedin.com/in/thedarcypeters/], Senior Customer Advocacy Manager at Buffer [https://www.linkedin.com/company/bufferapp/] and graduate of Leaders Who Coach™, about leadership, coaching skills, remote work, AI and the importance of staying human while work continues to move faster. Darcy shares insights from her career across customer advocacy, education, onboarding, technical support, entrepreneurship and her early leadership experience as a Captain in the US Marine Corps. This conversation explores how leaders can create trust, support growth, use AI thoughtfully, and hold space for people while still keeping accountability, focus and performance alive. Together, they explore: • How Darcy’s experience in the US Marine Corps shaped her leadership style • Why humility matters when leading people with more experience than you • How leaders can create space for others to bring their strengths forward • What remote connection looks like inside a globally distributed team • How Buffer builds trust, openness and human connection across time zones • Why asynchronous work still needs intentional human connection • How AI is changing problem-solving, decision-making and team conversations • Why leaders still need critical thinking, discernment and human judgement • How AI can help people self-coach before bringing ideas to the table • Why clarity and agreed priorities matter when everything feels fast and exciting • How leaders can support people through the pressure to “keep up” with AI • The value of coaching skills in monthly reflection conversations • Why listening for throwaway comments can reveal what really needs attention • How growth plans can be handled with care, rigour and accountability • Darcy’s biggest leadership growth moment and what it taught her about seeing people clearly This is a thoughtful and timely conversation about leadership in a changing world, using AI without outsourcing your thinking, and creating the kind of team environment where people can learn, speak up, grow and do meaningful work. If this episode resonates with you, you can connect with Darcy here: 👉 Darcy Peters on LinkedIn [https://www.linkedin.com/in/thedarcypeters/] 🎧 Listen & Follow Sehaam: LinkedIn: https://www.linkedin.com/in/sehaam/ [https://www.linkedin.com/in/sehaam/] YouTube: https://www.youtube.com/@SehaamCyrene [https://www.youtube.com/@SehaamCyrene] Instagram: https://www.instagram.com/sehaam.cyrene/ [https://www.instagram.com/sehaam.cyrene/] TikTok: https://tiktok.com/leaderswhocoach [https://tiktok.com/leaderswhocoach] 📲 Download the Leaders Who Coach™ App [https://coachlead.co/leaders-who-coach-app] and complete the Foundation Module free. 00:00 – Introduction 01:52 – Meet Darcy Peters 03:57 – Leadership lessons from the US Marine Corps 07:20 – Leading with humility and respect 11:47 – From military structure to entrepreneurship 13:09 – A typical day at Buffer 16:52 – Building connection in a remote team 21:02 – The power of in-person retreats 25:55 – How AI is changing team problem-solving 28:44 – Moving from approval to masterminding 31:55 – Critical thinking and AI 33:50 – Using AI to improve customer support workflows 38:55 – Staying focused when everything feels exciting 45:04 – Avoiding the AI rabbit hole 47:00 – Building shared AI learning across the team 53:33 – Using coaching skills in one-to-one conversations 58:54 – The pressure to keep up with AI 01:01:57 – Darcy’s biggest leadership growth moment 01:05:41 – Reflections on Leaders Who Coach™ 01:08:00 – Closing thoughts

1. juli 202657 min
episode Leading with Clarity with Caroline Mascarin 🎙️ artwork

Leading with Clarity with Caroline Mascarin 🎙️

What does it take to lead people well in a fast-moving Web3 business where the pace is high, the work is complex, and clarity matters every day? In this episode of the Leaders Who Coach™ Podcast, Sehaam Cyrene speaks with Caroline Mascarin, COO at Distributed Crafts, about leadership, operations, people-first culture and the human side of building in Web3. Caroline is a Web3 operations leader who looks after BOB, the Gateway to Bitcoin DeFi. With more than eight years in tech and more than four years in Web3, she works closely with ambitious founders to turn exciting ideas into durable, high-performing organisations. Her work includes recruiting global remote teams, introducing scalable operating systems and nurturing people-first cultures that support rapid growth. Caroline also shares her personal journey from growing up in Brazil to moving to London at 16, putting herself through college and university, and eventually finding her way into tech, operations and Bitcoin DeFi. Her early experiences shaped a deep interest in decentralisation, fairness and building organisations where people can operate with clarity, autonomy and shared purpose. Their conversation explores what it means to lead through rapid change, support people in remote and global teams, and create the kind of trust where honest conversations can happen early. Together, they explore: • Why people-first culture still needs structure, clarity and accountability  • How leaders can keep teams aligned when priorities are changing quickly  • Why it matters to socialise ideas before they are fully formed  • How Caroline’s leadership style has evolved over five years  • The importance of listening beyond the words people say  • Why small talk can give leaders important insight into how people are really doing  • How to give feedback with kindness, care and integrity  • The balance between frequent check-ins and micromanagement This is a thoughtful and practical conversation about leading with kindness, creating clarity in complexity, giving feedback with care, and building teams where people can grow, contribute and do meaningful work. If this episode resonates with you, you can connect with Caroline here:  👉 Caroline Mascarin on LinkedIn [https://www.linkedin.com/in/caroline-mascarin/] 🎧 Listen & Follow Sehaam: LinkedIn: https://www.linkedin.com/in/sehaam/ [https://www.linkedin.com/in/sehaam/] YouTube: https://www.youtube.com/@SehaamCyrene [https://www.youtube.com/@SehaamCyrene] Instagram: https://www.instagram.com/sehaam.cyrene/ [https://www.instagram.com/sehaam.cyrene/] TikTok: https://tiktok.com/leaderswhocoach [https://tiktok.com/leaderswhocoach] 📲 Download the Leaders Who Coach™ App and complete the Foundation Module free. Timestamps 00:00 Introduction to Coaching and Leadership 01:14 Caroline's Journey into Web3 and Operations 05:18 Navigating Rapid Change in a Growing Team 10:34 The Importance of Communication and Alignment 16:01 Leadership Style and Empathy in Management 20:56 Creating a Supportive Team Environment 26:24 Feedback and Growth: Balancing Kindness and Transparency 31:58 The Human Element in Leadership

13. maj 202638 min
episode Leading with Accountability and Care: Culture, Trust and Team Performance with Kate Lawson artwork

Leading with Accountability and Care: Culture, Trust and Team Performance with Kate Lawson

What does it take to build a people-first culture in fast-moving startups and scale-ups without losing accountability, clarity or care? In this episode of the Leaders Who Coach™ Podcast [https://www.youtube.com/watch?v=mGb8rCnSYoE&list=PLPqxRMw2Kajw-YYC9q9q56EFLx3CVZ3Q9], Sehaam Cyrene [https://www.linkedin.com/in/sehaam/] speaks with Kate Lawson [https://www.linkedin.com/in/kate-lawson06/], Founder and Director of Thrive Partnership [https://www.linkedin.com/company/thrive-partnership-ltd/], about what it really takes to build strong people and culture foundations in growing businesses. Kate shares insights from over 20 years working across people and culture, HR operations and executive support, including helping one insurtech scale-up grow from 4 people to more than 80 across the UK, US and Latin America.  This conversation explores how leaders can create psychological safety, support performance, and lead with fairness and transparency while navigating the pressure, pace and messiness of growth. Together, they explore: • Why all businesses are people businesses • Why looking after your people is essential to business success • How startups and scale-ups can put the right people foundations in place early • What leaders often overlook about people and culture when moving fast • Why psychological safety and accountability need to go hand in hand • How regular check-ins and honest conversations build trust • The importance of fairness, transparency and early conversations • Why line managers need more support than many organisations realise • How leaders can protect their own wellbeing during difficult people situations  • The role of community, physical wellbeing and boundaries in sustainable leadership  • Kate’s journey from corporate roles into founding Thrive Partnership This is a thoughtful and practical conversation about leadership, culture, wellbeing and creating environments where people can speak up, grow and perform at their best.  If this episode resonates with you, you can connect with Kate here:  👉 Kate Lawson on LinkedIn [https://www.linkedin.com/in/kate-lawson06/] 🎧 Listen & Follow Sehaam: LinkedIn: https://www.linkedin.com/in/sehaam/ [https://www.linkedin.com/in/sehaam/] YouTube: https://www.youtube.com/@SehaamCyrene [https://www.youtube.com/@SehaamCyrene] Instagram: https://www.instagram.com/sehaam.cyrene/ [https://www.instagram.com/sehaam.cyrene/] TikTok: https://tiktok.com/leaderswhocoach [https://tiktok.com/leaderswhocoach] 📲 Download the Leaders Who Coach™ App [https://coachlead.co/leaders-who-coach-app] and complete the Foundation Module free. 00:00 – Introduction 01:13 – Meet Kate Lawson 04:16 – Why people come first 11:52 – The realities of startup and scale-up growth 16:40 – What leaders struggle with most 22:34 – Scaling from 4 to 80 people 30:15 – Psychological safety and accountability 40:29 – Coaching, performance and leadership check-ins 41:59 – Protecting your wellbeing as a leader 53:03 – Kate’s biggest growth moment

21. apr. 202647 min
episode The Power of We: Leading with Responsibility, Credibility and Team Alignment 🎙️ with Jon Freedman artwork

The Power of We: Leading with Responsibility, Credibility and Team Alignment 🎙️ with Jon Freedman

What does it take to lead with clarity, credibility and responsibility in high-pressure environments? In this episode of the Leaders Who Coach™ Podcast, Sehaam Cyrene speaks with Jon Freedman, Fractional CTO and financial technology strategist, about what it really takes to build high-performing teams, create alignment and lead with impact in complex organisations. Jon shares insights from over 20 years in financial technology, working across investment banks and hedge funds, and scaling global teams in fast-paced, high-stakes environments.  This conversation explores how leaders can move beyond technical expertise and develop the communication, credibility and coaching skills needed to influence, align and grow teams effectively. Together, they explore: • Why responsibility (not ownership) is a powerful leadership mindset • How credibility is built through consistent behaviour over time • The importance of aligning teams around a clear “why” • Why technical expertise alone is not enough to differentiate yourself • How to handle strong opinions and disagreement in teams • The role of listening in effective leadership and decision-making • Why coaching is more effective than command-and-control leadership • Leading through ambiguity and communicating progress effectively • Scaling teams quickly while maintaining quality and cohesion • Why inclusive leadership (“we” not “I”) builds stronger teams This is a thoughtful and practical conversation about leadership maturity, communication and building teams that perform under pressure while remaining aligned and collaborative. If this episode resonates with you, you can connect with Jon here:  👉 Jon Freedman on LinkedIn [https://www.linkedin.com/in/jonfreedman/] 🎧 Listen & Follow Sehaam:  LinkedIn: https://www.linkedin.com/in/sehaam/ [https://www.linkedin.com/in/sehaam/] YouTube: https://www.youtube.com/@SehaamCyrene [https://www.youtube.com/@SehaamCyrene] Instagram: https://www.instagram.com/sehaam.cyrene/ [https://www.instagram.com/sehaam.cyrene/] TikTok: https://tiktok.com/leaderswhocoach [https://tiktok.com/leaderswhocoach] 📲 Download the Leaders Who Coach™ App and complete the Foundation Module free. 00:00 – Introduction to the episode 00:28 – Meet Jon Freedman and his background 02:47 – From Morgan Stanley to hedge funds: career journey 05:13 – Leadership vs management: showing up early as a leader 07:25 – Responsibility, credibility and trust in teams 09:39 – Differentiating beyond technical skills 12:00 – Aligning teams around the “why” 14:24 – Practising soft skills under pressure 15:44 – Communicating mission and building alignment 18:10 – Coaching vs command-and-control leadership 20:12 – Influencing decisions through coaching conversations 23:45 – Handling strong opinions and disagreement 25:51 – The importance of listening as a leader 27:37 – Building respect and avoiding “us vs them” 31:17 – Leading humans, not systems 33:45 – Balancing clarity, direction and flexibility 35:43 – Credibility and direct communication 38:03 – Leading through ambiguity and uncertainty 41:54 – Managing expectations and communicating progress 43:32 – Collaboration, transparency and trust 45:37 – Scaling a team from 7 to 90 people 48:12 – Hiring at speed: trade-offs and decision-making 52:32 – Building a high-performing and diverse team 55:51 – A defining leadership lesson: giving credit to others 58:05 – The power of “we” in leadership 01:00:26 – Final reflections

30. mar. 202648 min
episode How Leaders Build Trust, Growth and Accountability in Teams 🎙️ with Aditi Agarwal artwork

How Leaders Build Trust, Growth and Accountability in Teams 🎙️ with Aditi Agarwal

What does it take to lead high-performing teams through complexity, pressure and change? In this episode of the Leaders Who Coach™ Podcast, Sehaam Cyrene speaks with Aditi Agarwal, fractional CTO and technology delivery leader, about how trust, collaboration and deep listening shape effective leadership in fast-moving organisations. Aditi shares her journey from hands-on engineer to CTO, and the leadership lessons she’s learned while leading global technology teams through transformation, crisis moments and large-scale delivery challenges. Aditi Agarwal is a fractional CTO and technology delivery leader who works with PE-backed and scaling organisations during periods of transformation, platform change, and execution pressure. She’s previously served as Chief Technology Officer at Blue Light Card, Pizza Hut Digital Ventures, and Realife Tech, where she led global technology teams, large-scale platform rewrites, and digital growth initiatives. Now, she partners with executives and boards as an embedded operator, helping businesses modernise legacy technology, improve delivery effectiveness, and scale with confidence while continuing to operate at speed. Together, we explore: • Why collaboration unlocks stronger thinking and better decisions • Creating psychological safety so teams can express dissenting views • Why some conflict is healthy in high-performing teams • The leadership discipline of listening beyond the words people say • How lightweight feedback loops accelerate growth and confidence • Why asking for help is a critical (and often overlooked) leadership skill • Navigating leadership during crisis and high-pressure moments • Balancing executive leadership with the realities of family life • Why parents often develop exceptional prioritisation and leadership skills This is a thoughtful and practical conversation about trust, leadership maturity, and creating environments where people can do their best thinking and work together effectively. If this episode resonates with you, you can connect with Aditi here:  👉 Aditi Agarwal on LinkedIn [https://www.linkedin.com/in/aditiagarwal1/] 🎧 Listen & Follow Sehaam: LinkedIn: https://www.linkedin.com/in/sehaam/ [https://www.linkedin.com/in/sehaam/] YouTube: https://www.youtube.com/@SehaamCyrene [https://www.youtube.com/@SehaamCyrene] Instagram: https://www.instagram.com/sehaam.cyrene/ [https://www.instagram.com/sehaam.cyrene/] TikTok: https://tiktok.com/leaderswhocoach [https://tiktok.com/leaderswhocoach] 📲 Download the Leaders Who Coach™ App [https://coachlead.co/leaders-who-coach-app] and complete the Foundation Module free. TIMESTAMPS 00:18 – Meet Aditi Agarwal and her leadership journey 02:18 – From engineer to CTO: translating business and technology 05:00 – Why collaboration is essential for solving complex problems 08:40 – Aligning teams at the start of projects 11:20 – A simple exercise that builds connection in teams 13:40 – Why healthy conflict matters in teams 15:20 – Leading effective meetings with respect and clarity 17:52 – Building trust: “Someone has to go first” 19:00 – The responsibility leaders have to grow their people 21:30 – Using metrics and conversations to support development 24:30 – Habit tracking and building consistent behaviours 28:30 – The power of small, frequent feedback loops 31:59 – Listening for what people say, and what they don’t say 35:10 – Helping individuals express what they really think 39:40 – Leadership growth moments and navigating uncertainty 41:45 – Asking for help as a leadership strength 46:30 – Balancing CTO responsibilities with parenthood 49:00 – Navigating guilt and work-life balance as a leader

17. mar. 202645 min