AI, Honestly — EP002: Automating the Wrong Things

"Automating the Wrong Things"

30–35 min · March 2026

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This Episode

Every company says it's an AI company now. Almost none have asked whether they're ready to be. Kyle, Kate, and Morgan dig into the function being cut in the name of AI efficiency — and why the organizations eliminating it are the ones most likely to discover why it mattered.

Story 1

The Enterprise Architect

EA roles are being cut — in the name of AI efficiency. The judgment those roles provided isn't in any training set. And the AI replacing them doesn't know what questions to ask.

Story 2

You Can't Build AI on Broken Data

60% of AI projects will be abandoned due to data readiness issues. Zillow lost $500M not because the AI failed — but because the data it ran on didn't hold. The AI processed confidently either way.

The Driver Check

AI will accelerate whatever direction you point it. Before your next AI initiative, someone in the room needs to be able to answer three questions.

Do you know what you're actually asking? — Not the prompt. The underlying question the initiative depends on.
Can the foundation support what you're building? — Is the data clean? Are the APIs documented and rate-limited?
Who's driving? — Not who owns the project. Who has enough context to evaluate whether the AI's output is pointing somewhere real?

The companies that will be 24 months ahead aren't moving faster. They're answering these questions before they move at all.

Read the Driver Check →

Sources

The Cast

Kyle

Host. Opinionated. Expect a history drop.

Kate

The correspondent. Tight, sourced, no spin.

Morgan

The heartbeat. "Well, why though?"

Full Transcript

53 turns

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