AGL 438: Big Bet Leadership with John Rossman

About John

big-betJohn Rossman is a business strategist, operator, and expert on digital transformation, leadership, and business reinvention. He has consulted with many great brands including Novartis, Fidelity Investments, Microsoft, Walmart, and Nordstrom. He served as senior innovation advisor at T-Mobile and senior technology advisor to the Gates Foundation. He is an operator and builder whose love is diving into business problems and customer needs designing solutions and business opportunities.

Today We Talked About

  • Background
  • Outcomes
  • Michelangelo Quote – “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.”
  • Create Clarity
  • Maintain Velocity
  • Accelerate Risk and Value
  • Define the Future State
  • AI affecting Digital Transformation
  • Test plans
  • Active Skeptic
  • Communication
  • Craft a story, Repeat

Connect With John

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October 10, 2025
john rossman

AGL 438: Big Bet Leadership with John Rossman

About John John Rossman is a business strategist, operator, and expert on digital transformation, leadership, and business reinvention. He has consulted with many great brands including Novartis, Fidelity Investments, Microsoft, Walmart, and Nordstrom. He served as senior innovation advisor at T-Mobile and senior technology advisor to the Gates Foundation. He is an operator and builder whose love is diving into business problems and customer needs designing solutions and business opportunities. Today We Talked About Background Outcomes Michelangelo Quote – “The greater danger for most of us lies not in setting our aim too high and falling short, but in setting […]
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AGL 435: Garrett Rice

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