Intro

Chris Daigle and the show introduce the episode, guest Justin Trombold, and sponsor Chief AIOfficer.

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Episode notes

Most leaders aren’t struggling with AI tools, they’re struggling with how to lead the transformation those tools require.

In this episode, Chris interviews Justin Trombold, President of Antesyn Advisors who works with leadership teams navigating the uncertainty of generative AI strategy across industries from healthcare to enterprise services. During the conversation, he explains why most organizations go wrong by treating generative AI as an IT deployment rather than a transformation initiative, centralizing tool decisions while failing to connect use cases to business strategy, incentives, and operating models.

Chris and Justin unpack what it actually looks like to deploy AI in the real world: separating enterprise strategy from use-case experimentation, starting small with tightly defined pilots, defining KPIs before declaring success, and anticipating downstream bottlenecks that AI acceleration often creates. They also explore why cross-functional collaboration, incentive alignment, and curiosity matter more than technical horsepower — and why leaders must shift from “installing AI” to building organizational readiness for it.

If you want a practical lens for turning generative AI into measurable advantage — without triggering organizational friction — this episode is for you!

Chapters:

(00:00) Introduction

(02:01) Meet Justin Trombold

(05:03) What Companies Get Right — and Wrong — About Generative AI

(07:38) Why Generative AI Is Not an IT Project

(08:55) Centralizing Tools, Decentralizing Use Cases

(16:31) Who Should Be in the Room for AI Strategy

(17:28) Enterprise Strategy vs. Use Case Execution

(20:15) When AI Just Shifts the Bottleneck

(29:40) The Five Pillars of AI Readiness

(33:18) Designing Small AI Experiments That Scale

(41:09) Building Real AI Fluency Inside Your Organization