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Dean Carter

AI Took the Easy Part of Leadership. Here's What's Left.

Dean Carter spent years turning down the CEO job. "That's for crazy people," he'd say, watching leaders he respected get chewed up by it. So instead, he spent years reinventing the CHRO role he already had, and put it out there that this was the direction he wanted his career to go next. The job came to him anyway.

He's not a technologist who wandered into HR. He's an HR leader who now argues that AI is stripping the technical scaffolding out of every C-suite job. What's left over is the one thing leadership development has never actually been able to measure: judgment.

Dean is CEO of Instill, a culture-tech platform, and before that he spent 25 years as Chief People Officer, including a long run at Patagonia. He thinks leadership development has been measuring the wrong thing for decades, and that the tools built to fix it were never actually built to catch it.

What AI Means for the Future of Leadership Development
  38 min
What AI Means for the Future of Leadership Development
Work Tech Weekly
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Why Leadership Development Keeps Missing the Point

Ask any senior leader when they last got real, timely feedback about their own behavior, and you'll get a long pause. They can’t answer because they don’t know.

That’s Dean’s point. It’s also why his takedown of the standard toolkit is blunt: "Marcus Buckingham will say 360 feedback is the worst feedback ever. The only worse feedback you get is self-reporting."

Both diagnoses share a root problem. Self-report is grading your own homework, and everyone thinks they're a pretty good manager. The 360 runs into an older problem: Nobody tells the head honcho the truth. Power dynamics distort what gets said. Recency bias distorts what gets remembered. And even when the feedback is honest, it usually arrives months after the moment that mattered, filtered through a process everyone knows will eventually get traced back to somebody.

"I'm really biased about my performance," Dean says, "and I'm even more biased about everyone else's performance."

Dean's version of the failure mode is almost funny. Peers give anonymous feedback in a 360, the executive reads it, and immediately starts guessing — usually wrong — who said what. Was it Becky? Nobody in that exchange got better at anything. They just got paranoid.

Rebuilt: What a Leader Actually Does With the Signal

Dean draws on an example from his own career to illustrate why an outside perspective is valuable and why he’s built it into his product at Instill.

He once got a note — private, de-identified, sent only to him — flagging that in a recent meeting he'd done a solid job connecting with the room overall, but had really only engaged the three loudest voices. Two other people, based on the meeting's read, probably had something worth hearing and never got the chance.

So the next time, he called on them first. Both of them. Every time, since.

One of those two is based in Ukraine. "Her worry is, am I gonna have electricity and get bombed," Dean says — a completely different relationship to showing up and speaking in a meeting than everyone else in the room has the luxury of having. That's not a detail an engagement survey picks up. It's not a detail self-assessment picks up either, because Dean didn't know it was a blind spot until something told him.

Notice what this isn't: there's no dashboard here, no instrument, no "measurement system" anyone's proud of. It's a guy who got a piece of information he wouldn't otherwise have had, and changed what he did the next day because of it. That's the whole mechanism. The tool is incidental. The behavior change is the point — and it's a much lower bar than most leadership development programs manage to clear.

The Judgment Was Always the Job

Leadership development spent decades building frameworks and competency models to measure the technical edges of the job because those were the only parts anyone knew how to grade. AI just finished eating that part.

"You can AI a technical skill now," Dean says. "But you can't AI my life."

What's left isn't a smaller job. It's actually one of a leader's most important jobs — reading the room, noticing who didn't get called on, and doing something about it. Dean didn't build a tool to replace that. He built one to make it happen.

The judgment was always the job.

 

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