Leaders Who Coach™ PODCAST with Sehaam Cyrene
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
14 episodios
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