What does a CEO actually want from their CHRO? Aaron Skonnard, the founder and former CEO of Pluralsight, has a more specific answer than most. Aaron co-founded Pluralsight in 2004, scaled it past $600M in revenue, took it public on Nasdaq, and sold it to Vista Equity Partners in 2021 at a $3.5B valuation. He hired Anita Grantham as the company's first CHRO, and in this rare episode, the two of them sit on opposite sides of the table to break down the partnership that ran the business for the next decade.

This is the only Culture Creators episode where Anita interviews a CEO she actually built something with. The conversation is candid, specific, and full of the kind of operating detail HR leaders rarely get on camera, including the interview question that filtered Aaron in, the weekly coaching commitment that reshaped the executive team, and the moment Aaron realized he was the bottleneck.

What you'll learn: 

• The interview question that tests whether a CEO is coachable (and whether they deserve a CHRO who tells them the truth)

• Why Aaron treats vision and culture as a sequence, not a stack, and how Pluralsight built a multi-page five-year picture

• The confidentiality contract that lets a CHRO be a peer to the C-suite and an advisor to the CEO at the same time

• How to get in front of an executive's exit before the resignation is already written

Chapters:

0:00 Cold open

4:00 The "most trusted advisor" framing

8:15 The interview question: "Are you willing to be coached?"

12:00 Weekly coaching for every C-suite executive

18:00 Why a vision statement is not a vision

32:00 The arm's-length CHRO problem

35:15 The confidentiality contract

43:30 "I actually am the problem."

50:00 Get in before they quit

54:15 Aaron's biggest regret as a CEO