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"Compliance doesn’t make you good—so how do you really know if your tech team is any good at all?"



In this episode, Adam sits down with Andy Graham, former CTO with 30 years of M&A and enterprise tech leadership, and Dane Eldridge, serial entrepreneur and CEO of Stackup. Together, they’ve built a deceptively simple tool that’s flipping the script on how tech leaders assess their teams—and uncover hidden risks before they explode.

You’ll learn why most CTOs are unknowingly flying blind, how to detect the silent killers of innovation (like misaligned architecture or fuzzy definitions of "automation"), and how a single 30-minute assessment can surface the unknown unknowns holding your business back. Whether you're a scaleup CTO, a board member trying to evaluate tech health, or a founder wondering if your dev team is as strong as they say—they break down the real reason so many companies move slow, and how to fix it. You'll walk away with a new lens on language, leadership, and the hidden liabilities inside most tech functions.

You’ll Learn:

• How benchmarking reveals hidden risks and weak spots in your tech function
• Why compliance frameworks can create a false sense of confidence
• How to detect misalignment between your tech strategy and business goals
• What most CTOs miss about the real cost of technical debt during scale-up
• Why “automation” means different things to different teams—and why that’s dangerous
• How to use Stackup’s 30-minute assessment to surface unknown unknowns
• What poor communication habits are silently sabotaging CTO credibility
• How to use objective scoring to drive strategic investment and track improvement over time

Timestamps:

[00:00] Introduction

[04:41] Common pitfalls in developer-turned-CTOs

[06:33] Triggers for assessing your tech function

[08:00] How Stackup surfaces unknown unknowns

[09:23] Real-world horror stories that drive urgency

[10:07] Why misaligned language leads to costly misunderstandings

[11:56] When tech due diligence reveals million-dollar mistakes

[13:35] What technical debt really costs in scaleups

[14:20] Why early architecture choices are critical

[16:14] Planning upgrades with trigger points

[17:45] How Stackup supports smarter, faster decisions

[20:39] Why slowness doesn’t show up on the P&L

[26:15] Using storytelling to align leadership around tech

[28:01] What Stackup assesses in just 30 minutes

[29:47] Simple questions that reveal massive security flaws

[31:08] Why shiny tools like AI won’t fix misalignment

[33:22] How to counter hype with strategy and expectations

[35:31] When to use Stackup as a new or evolving CTO

[37:59] Proving your tech value with objective results

[39:13] Why Stackup delivers reports in video and podcast formats

[41:19] Running the assessment quarterly to track growth

[43:12] Focusing on just four priorities for maximum ROI

[45:10] How the scoring system ensures objectivity

[47:31] Why most leaders want to improve—transparently

[49:12] Upcoming AI-powered CTO assistant and benchmarking

[52:06] Using Stackup data to shape strategy and performance

You can follow Andy and Dane on LinkedIn and learn more about their work here.

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