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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Keegan-Michael Key & Tituss Burgess