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What if the biggest challenge in scaling your organization isn’t execution, but knowing where you actually are?

In this episode, I sit down with James Webster, former Amazon engineer and founder of Sheep CRM, to unpack a deceptively simple idea that cuts through years of confusion around operational maturity. James introduces his Three Mountains model, a practical way for CTOs to assess reality without ego, optimism, or wishful thinking.

We talk about what CTO leadership really looks like during hypergrowth, why engineering leadership breaks when teams skip stages, and how misaligned expectations quietly derail even strong organizations. Drawing from James’s experience inside Amazon and years working with scaling teams, we explore why clarity beats speed, and why naming constraints honestly is a leadership advantage, not a liability.

If you’re navigating startup scaling, leading teams through change, or trying to align technology with business reality, this conversation will help you reset your internal compass.

This episode is about perspective, precision, and building from where you are, not where you wish you were.

You’ll Learn:

[00:00] Introduction

[01:08] Why scaling fails when leaders misread where they actually are

[02:21] How Amazon hypergrowth reshaped James Webster’s view of pace and pressure

[03:37] Why constant role change breaks traditional playbooks

[14:26] Why thinking too far ahead undermines real transformation

[41:12] How repeated problems signal when process really matters

[42:18] Why “sloppy” processes beat perfection early on

[43:34] How optimism bias keeps leaders from seeing reality

[47:09] Why losing your position on the map becomes dangerous at speed

[48:22] How choosing the right problem changes everything

You can connect with James on LinkedIn and learn more about his work on his website here.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

794: A 2009 Interview with Jeffrey Ford at the World Fantasy Convention