Artwork for podcast The Executive Appeal with Alex D. Tremble
EP 229: How Multi-Location CEOs Escape Being the Only Decision-Maker in the Room
Episode 2298th July 2026 • The Executive Appeal with Alex D. Tremble • Alex D. Tremble
00:00:00 00:39:11

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Two years and a significant investment into a technology decision, Simon Kaye recognized it was the wrong call and walked away, even as his own vendor questioned how he could abandon that much sunk cost.

That willingness to admit a mistake and act on it is central to how Jaguar Freight has operated for over 33 years without every decision escalating back to Simon's desk.

Simon Kaye is the founder and CEO of Jaguar Freight, a global logistics company he built from a single office in 1993 into a fully distributed operation trusted by leading global brands, powered by his proprietary Cybertrax platform.

In this episode of The Executive Appeal, Simon discusses:

  • Building a culture where employees are expected to challenge leadership decisions
  • Why admitting a mistake early is a leadership strength, not a weakness
  • How cutting a failing initiative early protects margin more effectively than defending it
  • The hidden risk created by client concentration
  • Where AI fits as a complement to people, not a replacement for judgment

This conversation is for CEOs and executives who are still the final approval on every major decision, or whose leadership teams tend to tell them what they want to hear rather than what they need to know.

Listen to the full episode and take the free Scorecard Diagnostic to identify your organization's leadership bottleneck:

https://gpsleadership.org/scorecard/

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