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Watch this happen to exceptionally capable people. CHROs who transformed functions, built credibility, did everything right in the mandate conversation, and still hit a ceiling they cannot explain.

We talk about the identity shift the CHRO must make. Functional leader to business leader. HR expert to enterprise problem solver.

But here's what no one talks about. The CHRO cannot complete that shift alone. There's a corresponding shift the CEO must also make. If the CEO doesn't make it, the CHRO's transformation stalls.

What You'll Learn

The structural trap no one names:

• Why the CHRO is the only executive whose job requires them to assess their boss
• How capable CHROs become structurally trapped
• The difference between being a trusted HR partner vs. someone the CEO lets see them clearly

What the CEO identity shift looks like:

• Moving from "I have a trusted HR partner" to "I have someone whose job includes seeing me clearly, and I have to let them"
• Signs the CEO has made the shift: used as confidant, in the room when decisions are shaped
• Signs the CEO hasn't: learning about decisions after they're made, execution without diagnosis

The four-move playbook:

1. Watch how the CEO manages struggling peers: Are you confidant, neutral observer, or excluded?
2. Name the dynamic before the board does: Have a direct conversation about what happens when the board asks about their effectiveness.
3. Test the relationship early: In the first 90 days, bring an uncomfortable but grounded observation.
4. Accept the limitation: You cannot assess whether the CEO has made the identity shift until things get hard.

Key Quotes

"This is the only executive relationship where a subordinate is structurally required to assess their boss as part of the job."

"I've always made one commitment to CEOs I work for: I will never tell the board anything I haven't shared with you first. No surprises."

"Some CHRO failures blamed on the CHRO are actually dependency failures. The CEO never made the shift."

The Diagnostic Questions

• When you raise difficult observations, does the conversation continue or does nothing change?
• Are you positioned as confidant, neutral observer, or excluded when the CEO manages struggling peers?
• Have you discussed what happens when the board asks about their effectiveness?
• Are you in the room when difficult decisions are shaped, or only when they're implementing the plan?

Resources

• My Talent Sherpa: mytalentsherpa.com
• Talent Sherpa Substack: talentsherpa.substack.com
• Scott Morris / Propulsion AI: getpropulsion.ai
• Dripify: try.dripify.com/talentsherpa