226: How to Continue, Kill, or Pivot Your Pilots with Clarity and Confidence

In this episode of the Innovation Storytellers Show, I sit down with John Rossman, the former Amazon executive who helped launch the Amazon Marketplace and is a co-author of Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era. Our title says it all: How to Continue, Kill, or Pivot Your Pilots with Clarity and Confidence. 

John and I get practical about the moments that make or break innovation programs, from shaping the problem statement to running the high-stakes meetings where leaders must choose a path. If you have ever wondered why competent pilots stall, or how to defend a tough call in the room, this one is for you.

John takes me inside the “working backwards” mindset and the rewired playbook he built with T-Mobile’s new business incubation team in Bellevue. We also dig into how decisions actually get made. 

John lays out the discipline behind those pivotal Continue, Kill, Pivot, or Confusion meetings, including clear criteria, facilitation, and communications so decisions stick rather than drift into ghost projects. We discuss strategic communication and the role of the Chief Repeating Officer, drawing lessons from successes at Amazon and hard-won insights, such as the Gates Foundation’s inBloom post-mortem, where great technology and funding still failed without a proactive narrative that addressed resistance.

You will hear how I approach innovation culture as an anthropologist, treating every company like its own country, with its own history, norms, and incentives that shape what is possible. We explore tools that invite people into the future rather than dictate it, such as “imagine if” framing and pre-mortems, which surface risks without killing momentum.

 John also shares a few provocative ideas he believes the world needs now, from real-time freedom to shift cloud workloads to snap-switching your mobile carrier, all designed to put choice and competition back in the hands of users.

If you are juggling pilots and pressure, this conversation gives you a plain-English playbook for moving from noise to momentum. You will leave with concrete steps to sharpen your problem statements, wire your experiments to the P&L, structure decisive meetings, and communicate like a leader who can carry a big bet across the line. Listen in, take notes, and get ready to make your next decision with clarity and confidence.