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352 Big Bets and the Future of Leadership with John Rossman, Author of Big Bet Leadership

Wednesday 10th July 2024
FYD EPISODE 352 John Rossman

On this episode of Christopher Lochhead: Follow Your Different, we are joined by our friend and multi-time guest, John Rossman.

John Rossman is a Master of Innovation and former Amazon Executive who brings to the table his insights from his new book, Big Bet Leadership: Your playbook for winning in the hyper digital era. His experiences with industry giants illuminate the path for making bold, transformative decisions.

This conversation is a deep dive into the courage and strategy required to lead in uncertain times, focusing on big bets that redefine industries, in an era where navigating technological change is crucial.

You’re listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let’s go.

John Rossman on Category Design and Big Bet Leadership

Christopher and John discuss the impact of category transformation and AI on businesses. John expresses gratitude for Christopher’s influential work on category design, which has shaped his thinking and client engagements positively.

They then delve into the challenges faced by companies in making big bets and succeeding in transformations, particularly in the context of AI and digital eras. Both acknowledge the historical struggle of major corporations to adapt and innovate compared to startups.

John emphasizes the need for senior leaders to rethink traditional approaches and embrace new strategies to navigate the hyper-digital era successfully and achieve substantial productivity gains.

John Rossman on Bold Moves vs Incremental Improvements

Christopher and John explore the necessity of both incremental improvements and bold moves in corporate leadership. They stress the importance of executives balancing ongoing operations with strategic innovation, emphasizing the need for a portfolio of big bets alongside incremental changes.

Drawing on insights from successful leaders like Satya Nadella, Jeff Bezos, and Elon Musk, they highlight the challenges of leading transformations in established companies. They propose a framework centered on creating clarity, maintaining velocity, and accelerating risk and value to guide organizations towards systematic transformation.

Customer Obsession and Customer-Driven Innovation

Christopher and John then talk about the importance of customer obsession and strategic thinking in driving successful business transformations. They critique competitor-focused strategies and highlight the significance of understanding customer problems deeply.

Drawing from Amazon’s approach, they emphasize the need for a portfolio of hypotheses and ideas, continuously testing and iterating before scaling.

Both caution against premature scaling and advocate for a patient approach that prioritizes operational readiness and sustainability. They stress that a combination of tactics, including customer obsession, agile methodologies, and strategic experimentation, is essential for systematic innovation and transformation.

To hear more from John Rossman and how to make Big Bets for your company, download and listen to this episode.


John Rossman
Digital and Innovation Advisor

Mr. Rossman is an expert at digital business models, operations and organizing programs. He has led engagements on developing innovation processes, Internet of Things strategies, marketplace and API driven platform business models.

He is a sought-after speaker on creating a culture of operational excellence and innovation.

Mr. Rossman has worked with clients across various industries, including retail, insurance, education, healthcare, consumer products, industrial products and transportation.

Mr. Rossman’s notable assignments include The Bill and Melinda Gates Foundation, Microsoft, Nordstrom and several of the world’s leading retail and insurance organizations.

Prior to Rossman Partners, John was a Managing Director at Alvarez and Marsal, a performance improvement consulting firm.

Prior to A&M, John was an executive at where he launched the Marketplace business and third-party selling platform, and ran the merchant services business.


Connect with John Rossman!

LinkedIn: in/John-Rossman | Twitter: @JohnERossman | Get the book: Big Bet Leadership

We hope you enjoyed this episode of Christopher Lochhead: Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitterInstagram, and subscribe on Apple Podcast / Spotify!