13 May 2024

Season 4, Episode 25. Big Bet Leadership with John Rossman

How can leaders approach digital transformation differently to increase their chances of success in the rapidly changing business landscape?


In this episode of the Innovation Meets Leadership podcast, host Natalie Born interviews John Rossman, a former Amazon executive and the author of four books on leadership, innovation, and transformation. Rossman shares valuable insights from his latest book, "Big Bet Leadership," which aims to help senior executives navigate the challenges of digital transformation in the hyper-digital era. He emphasizes the importance of senior leadership's commitment to change, creating clarity, and adopting new approaches to drive successful transformations. Rossman also discusses the role of the aging workforce and the need for companies to automate processes and empower their employees to focus on higher-value activities.


John Rossman is the author of four books on leadership and business innovation including the best-seller The Amazon Way and Big Bet Leadership. He is an early Amazon executive who played a key role in launching the Amazon marketplace business in 2002. Today he is a leading keynote speaker on leadership for innovation and transformation. John is an operator and builder whose love is diving into business problems and customer needs designing innovative solutions and business models and creating durable enterprise value. He has served as the senior technology advisor at the Gates Foundation and senior innovation advisor at T-Mobile.


His new book, Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era, is an actionable playbook for senior leaders to succeed at complex transformations.


00:00:00 - 00:04:59 - From Amazon to Guiding Digital Transformation

- John Rossman's background as an early leader at Amazon and his transition to helping companies with digital transformation

- The progression of Rossman's four books, culminating in "Big Bet Leadership"

- The three mega forces shaping the hyper-digital era: technology, aging workforce, and economic growth through productivity and innovation


00:05:00 - 00:10:59 - Transforming Mindsets and Approaches

- The importance of senior leadership's commitment to change and making adjustments to their approach

- The three sections of "Big Bet Leadership": thinking, environment, and management

- The three habits of successful leaders in major transformations: creating clarity, maintaining velocity, and accelerating risk and value


00:11:00 - 00:17:59 - The Power of Writing and Debating Memos

- The benefits of using memos instead of PowerPoint presentations for complex situations

- How the Amazon way of writing and debating memos leads to better decision-making and understanding

- The importance of completeness of thought and simplicity of wording in creating clear messaging


00:18:00 - 00:22:59 - Key Adjustments for Successful Digital Transformation

- Creating a common definition of the problem and the hypothesized solution

- The importance of full-time leadership and teams for major transformations

- Embracing the journey of experimentation and learning in strategic wandering


00:23:00 - 00:27:00 - Embracing Ambition and Aiming High

- The impact of the aging workforce on digital transformation and the need for automation and empowering employees

- The importance of approaching problems holistically, not just applying technology

- Michelangelo's quote on the danger of setting aims too low and the need for ambitious goals


Key Quotes:

"It truly is. I think the difference is about getting senior leadership to make a few adjustments. Not on everything they do, but on how they run these major transformations." - John Rossman


"The greater danger for most of us lies not in setting our aim too high and falling short, but in setting our aim too low and achieving our mark." - Michelangelo, as quoted by John Rossman


Connect with John:

Website: https://johnrossman.com/


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