If you don’t fix the fundamentals, you merely accelerate chaos. Salesforce AI readiness starts with data quality, process clarity, and governance—not demos.

Everyone wants to “buy AI,” but few CIOs are willing to do the unglamorous work of fixing the Salesforce data and operating discipline that AI depends on. In this episode of Heartbeat: Tactical Insights for CIOs, Mike Sommer sits down with Phil, a veteran tech executive and CIO, to dismantle the myths around digital transformation, Salesforce customization, and when outside advisors help (and when they don’t).

Phil makes the case that the modern CIO must evolve from “order taker” to Chief Education Officer—teaching the business why “boring” governance is the real path to safe automation and AI.

In this episode, we cover:

- The AI Paradox: Why automating broken processes creates faster failure - Truth vs. Theater: How CIOs get an objective view of reality (internally vs. selectively external) - Salesforce Strategy: The “Zappos rule” for what to customize vs. keep out-of-the-box - The Funding Move: Using AI urgency to unlock budget for technical debt + data remediation - Transformation War Stories: The hidden cost of shadow IT and vendor sprawl

Why this matters now

Pressure to adopt AI (and Agentforce-style automation) is high—but the risk of hallucinations, misrouted work, and structural failure is higher if your foundation is unstable. This conversation gives CIOs a practical script to align business + IT, secure funding for fundamentals, and earn confidence instead of selling change.

Confidence OS Brief (subscribe): https://mikesommer.substack.com/

Follow Mike Sommer on LinkedIn: https://www.linkedin.com/in/mikesommer/