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Big Bets and Bold Leadership with John Rossman

Transforming Your Business and Customer Experience

Shep Hyken interviews John Rossman, executive coach, advisor, and keynote speaker on leadership, innovation, and transformation. He talks about leading big bets and driving successful organizational transformations – which is especially important when leading a customer service or CX initiative.

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This episode of Amazing Business Radio with Shep Hyken answers the following questions and more:

  1. What is a “big bet” in business?
  2. How does the future press release technique communicate the vision of a transformation to employees and stakeholders?
  3. What is the chief repeating officer, and how do they contribute to improving customer experience?
  4. What causes organizational transformations to fail?
  5. What role does gaining true senior executive alignment play in the success of transformative initiatives?

Top Takeaways

  • A big bet is any concept, approach, project, or strategy with a high potential for impacting our customers and business.
  • Effective leaders communicate their vision clearly. They use techniques including writing memos, defining the desired outcome, and creating future press releases to make the vision concrete and understandable. This approach rallies everyone in the organization around a common goal and gives them a clear understanding of their roles in achieving it.
  • Smart communication methods can inspire and mobilize employees. Mission and vision statements should be clear, simple, and focused on the desired outcomes. By consistently repeating the organization’s mission and vision, leaders create a unified and empowered workforce.
  • Obtaining genuine alignment among senior leaders is critical to the success of transformative initiatives. Ensuring that leaders truly understand the mission, outcomes, and implications of the transformation helps to overcome organizational silos and fosters collaboration.
  • Leading organizational transformations demands an understanding of potential resistance points. Acknowledging challenges and being empathetic towards potential pushback from teams can help in creating a smoother transition.
  • Plus, John shares transformation strategies that successful leaders and organizations implement from his new book, Big Bet Leadership. Tune in!


“The best transformations you can undertake are those that impact your customers directly. It’s all about understanding the problem and outcomes your customers are trying to achieve.”

“Think slowly, act fast. Write out what you envision as the solution to your customer’s problem. By writing these out, you’re experimenting before you even start building something, clarifying and simplifying the real problems you are trying to solve.”

“So many transformations fail because we are vague about the problem we’re trying to solve and the future state that we are trying to get to. The high-risk components of a transformation must be tested before we commit to it.”

” Gaining true senior executive alignment is critical for successful transformations. They must know where it’s going and their role in making the transformation happen.


John Rossman is the author of four books on leadership, business, and customer experience, including the bestseller The Amazon Way. His latest book, Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era, is available today.

Shep Hyken is a customer service and experience expert, New York Times bestselling author, award-winning keynote speaker, and host of Amazing Business Radio.

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