Are you running faster with AI, or just running blind?

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Most teams don’t lack data, they lack understanding. Today, I sit down with CTO Jason McGhee, who has spent years inside analytics, machine learning, and product teams asking the hard question: why is the data changing?

AI in analytics works best when it supports human judgment instead of replacing it. A hybrid approach keeps people involved while AI assists with complex tasks, making decisions clearer and systems easier to reason about. Moving faster with AI increases risk when teams cannot explain why the data is changing.

Both recurring reports and one-off investigations break down without context. Dashboards often fail as real deliverables because they separate numbers from explanation. Insight becomes more actionable when it is shared alongside the data itself. Screenshots, slide decks, and disconnected tools add friction, making validation harder and discouraging deeper questions from leaders.

If you care about data-driven decision making, want a more honest relationship with machine learning outputs, or are figuring out how generative AI fits into real-world business analytics, this conversation sharpens how you think about data, trust, and momentum as a technology leader.

You’ll Learn:

[00:00] Introduction

[02:45] Why more data doesn’t help if you can’t explain what changed

[05:12] How keeping humans in the loop changes AI analytics failure modes

[09:48] Why dashboards break down once they leave the builder’s hands

[14:32] How AI turns big analytical questions into auditable steps

[20:41] Why one-off and recurring reports need shared intuition to work

[27:18] How screenshots and slide decks quietly block data validation

[34:55] Why faster AI increases the risk of running in the wrong direction

[43:07] How mixing structured data with Slack adds missing business context

[57:26] The leadership cost of treating analytics as outputs, not understanding

For more information you can also visit writ.so.

You can connect with Jason on his personal LinkedIn or his business LinkedIn.

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.