Can your organization survive its own hesitation to take bold bets?
Today on Digital Disruption, we’re joined by former Amazon exec and bestselling author, John Rossman.
John is an author, business advisor, and keynote speaker. He was an early Amazon executive who played a key role in launching the Amazon marketplace business in 2002. He has served as the senior technology advisor at the Gates Foundation and senior innovation advisor at T-Mobile. His books include “The Amazon Way” and “Think Like Amazon.” His new book, Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era, is an actionable guide for leaders who want to succeed in complex transformations.
John sits down with Geoff to unpack why most change initiatives fall short, and what leaders can do to shift the odds in their favor. Looking back on his experience launching Amazon Marketplace and advising top organizations, he shares strategies for scaling effectively, leading through change, and building resilience in today’s digital environment. John explains why traditional transformation efforts often fail, the issues leaders come across, and how to adopt a system of risk-smart decision-making and drive meaningful change. Get ready to challenge assumptions, cut through the hype, and transform the way you lead.
In this episode:
00:00 Intro
01:07 Solving hard problems with an integrated mindset
03:07 Why most companies struggle with change
04:21 The 3 megatrends disrupting business
06:32 Why Back-office productivity must change
07:22 Why Past winners are at risk of losing
09:36 Why big bets often fail
13:30 The three habits of big bet leaders
16:42 Why innovation labs often fail
21:39 Why leaders must design decision points intentionally
25:03 The power of a clear “Big Bet Vector”
31:27 What extreme accountability really means
36:08 Should we abandon silos?
40:25 Advice for how CIOs can unlock progress despite technical debt
46:08 How CIOs can win
51:55 Why Change can’t just be an operator’s job
53:01 The Big Bet Playbook explained
56:27 Active skepticism
Website: https://johnrossman.com/
LinkedIn: https://www.linkedin.com/in/john-rossman/
X: https://x.com/johnerossman
Connect with John:
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