76: How Great CTOs Influence Regulators, Auditors, and Certifications

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What if the real blocker in your certification isn’t the rules at all, but how you’re playing the game?



What really happens when you treat compliance like a fixed checklist and then get hit with yet another vague delay? I take you into the moment a CTO realized that being technically right still left him carrying months of uncertainty on his shoulders. That crack in his old mental model opened the door to seeing regulation as a human system shaped by people instead of boxes to tick.

The same compliance posture can lead to totally different timelines depending on relationships, incentives, and how you show up in the room. Instead of obsessing over perfection, the focus shifts to mapping the people in the process and asking sharper questions that actually move things forward. By the end of this episode, you’ll see how small moves of influence can change a certification journey that once felt completely out of your hands.

You’ll Learn:

[00:00] Introduction

[01:12] Why the real certification roadblock is rarely the checklist

[03:56] What changes when you treat compliance as a human system instead of binary rules

[05:22] The question that flips frustration into influence and momentum

[07:18] How a single shift in communication makes leadership lean in

[08:42] The reason two identical compliance postures get wildly different timelines

[09:31] How mapping people instead of tasks reveals hidden bottlenecks and unstuck paths

[11:54] What a high-stakes UK implementation showed about friction-free compliance

[14:38] Why aligned incentives accelerate timelines faster than documentation ever will

[17:42] Where influence replaces waiting and CTOs move from reactive to strategic

[18:22] Five steps that turn regulatory uncertainty into predictable progress

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