What if modernization wasn’t about the next hype cycle…but about the courage to ask questions and a reframing of the exam question altogether?

In this holiday special, we're looking back on some of our favorite conversations that shaped 2025 — the ones that challenged us to rethink risk, rethink modernization, and rethink what “doing the right thing” actually looks like. 

Happy Holidays!

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In this episode, host Irene speaks with David Linthicum, a leading figure in cloud computing and digital transformation. 

They explore the risks associated with following technology trends without understanding their business value. David shares insights from his extensive experience at the top of one of the world's leading consultancies, highlighting patterns of failure in technology adoption, the pressures leaders face, and the importance of a pragmatic approach to decision-making.

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In this episode of On A Limb, host Irene speaks with Alastair Levy, a seasoned leadership advisor and executive coach, about the evolving landscape of business risks and the complex challenges leaders face today. 

Alastair shares insights from his diverse career, emphasizing the importance of systems thinking, the balance between short-term and long-term objectives, and the courage required in leadership decisions. He also draws parallels between conducting orchestras and leading organizations. 

The conversation highlights the need for leaders to adapt to a rapidly changing world while fostering a culture of reflection and open dialogue.

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In this episode of "On A Limb," host Irene delves into the world of AI hype with Nikhil Suresh, founder and CEO of Hermit Technology. Known for his critical stance on Silicon Valley's obsession with AI, Nikhil discusses the real cost of AI hype on business decisions. From the dangers of symbolic efforts to the widespread distraction caused by AI trends, this conversation explores how businesses can navigate the AI landscape with critical thinking and genuine attention. Tune in to discover whether AI is truly solving problems or just a buzzword masking deeper issues.

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In this episode, Irene is joined by Samuel Arbesman, PhD, to discuss his new book, 'The Magic of Code'.

With a Ph.D. in computational biology from Cornell University, Sam currently serves as Scientist-in-Residence at Lux Capital. He’s well known for his writings, published in Wired, The New Yorker, The Atlantic, among others, and he’s authored several popular books.

Sam and Irene discuss the importance of rekindling wonder in our relationship with technology, the historical context of computing, and the responsibility that comes with the power of software. They delve deep into the importance of developing a more holistic approach to computing education that draws from history and human experience while reflecting on the risks of neglecting the humanistic elements in technology and the need for deliberate engagement with these systems. 

You can get a copy of Sam's new book here.

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In this episode of On A Limb, host Irene Sandler chats to Logan Allin, founder and Managing Partner of global investment firm Fin Capital, about the critical state of America's financial IT systems and why he believes this is America's Great Infrastructure Challenge. 

They delve into the challenges of modernizing outdated banking systems, the catastrophic risks associated with legacy technology, and the potential impact of technical debt on financial institutions. 

Logan shares his views on the biggest mistakes banks make when attempting to modernize, the importance of aligned incentivization, and the critical need to move quickly.

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In this episode, Irene sits down with world-renowned financial services transformation expert, Dr. Leda Glyptis.

With two decades of experience driving modernization in financial institutions, Leda unpacks the risks of resisting change and the critical need for banks to adapt in an increasingly dynamic landscape.

She explores the impact of regulation, the human factors that often derail transformation efforts, and the challenges of breaking free from the comfort of the status quo.

This insightful conversation is a must-listen for anyone navigating change in financial services.

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In this conversation, the celebrated retail analyst and ex-CTO, Paula Rosenblum, and Irene discuss the critical need for modernization in customer service systems across the global retail industry. 

They emphasize the importance of extensibility in solving the challenges posed by legacy systems, as well as how IT leadership can manage organizational inhibitors that hinder change. 

The discussion also highlights the significance of customer experience and effective change management strategies in navigating these obstacles. 

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In this episode, Irene is joined by British politician Liam Byrne. Liam is a Labour MP for Birmingham Hodge Hill, a member of His Majesty's Privy Council, elected chair of the Global Parliamentary Network on the World Bank and IMF, and chair of the House of Commons Business and Trade Select Committee. He's also a former Gwillem Gibbon Research Fellow at Nuffield College Oxford, an honorary professor at the University of Birmingham and author of over 20 publications on economics, foreign policy and public service reform.

Liam and Irene discuss his background in public service and business, the current state of the UK economy, and the challenges of inequality and populism. Liam emphasizes the need for a modern supply-side economic strategy, addressing productivity issues, and the importance of innovation supported by government policy. 

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Margaret Exley, CBE, is the Chairman and Founder of SCT Consultants,  a management consultancy specialising in board evaluation and development. 

A highly sought-after change management expert, Margaret advises the most senior levels of business and central government on how to navigate risk, in pursuit of growth.

In this episode, Irene and Margaret delve into the evolving role of corporate boards and explore how they can enhance their effectiveness. Margaret shares her wisdom on how companies can adapt to rapid changes in the business environment so they are better equipped to handle increasingly complex operational and reputational challenges. 

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In this episode, we sit down with Peter Donald, Founder & Managing Director of Arena Advisory Group, a leading reputation management firm.

As former Assistant Police Commissioner at the New York Police Department (NYPD) and FBI Spokesperson, Peter has been on the front line of some of the world's most challenging and complex reputational issues. 

Sharing experience in both public and corporate sectors, Peter delves into the intricate dynamics of trust and reputation in today’s fast-evolving technology-driven landscape. He sheds light on how reputations can be tarnished in the blink of an eye and how trust can be built and sustained in an era where information moves faster than ever.

Peter shares insights on how companies can proactively manage their online presence, protect their brand from misinformation, and leverage transparency as a competitive advantage. 

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Recent Mechanical Orchard research found that 71% of enterprise IT leaders find modernization stressful.

In this episode, we are joined by transformational technology leader and veteran CTO, Paul Gaffney, who shares his wisdom on how to find joy in modernization, even when the mountain looks too big to climb. 

We dive into:

• The root causes of joyless modernization
• Why Paul’s philosophy of 'having fun while delivering' is so important in the context of modernization
• What IT leaders can do to bring joy to modernization and what impact this might have on a personal and business level

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In our inaugural episode, we welcome Professor Herb Krasner, Founder and former Chairman of the Software Quality Institute at the University of Texas.

Together, we delve into the concept of technical debt and the significant risks that poor-quality software presents to the global business landscape.

We explore the critical need to proactively address technical debt to prevent costly operational and reputational issues. Professor Krasner shares his insights on potential solutions that can help businesses avoid a crisis, offering valuable expertise on navigating this complex challenge.

Don’t miss this episode to gain a deeper understanding of technical debt and its far-reaching implications.

You can find more about Professor Krasner's work here https://www.it-cisq.org/wp-content/uploads/sites/6/2022/11/CPSQ-Report-Nov-22-2.pdf

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