Get a candid look into what it takes to create the ideal CEO/CHRO partnership
In this episode, Anita Grantham interviews Aaron Skonnard, the founder and former CEO of Pluralsight. Anita was Aaron's first CHRO. Together, they scaled the business past 600 million in revenue and sold it for 3.5 billion dollars.
This is the only Culture Creators episode where the host (Anita) has worked with the guest. They are open, honest, and share the operating playbook they used for a decade.
👀 Here's what you get in today's edition of the Culture Creators:
The interview question Anita Grantham asked Aaron Skonnard that filtered every other CEO she has interviewed since
Why every C-level executive at Pluralsight kept a weekly coach for years, and what changed in the room because of it
The retention play that only works if the CHRO already has the relationship in place
Check out the episode wherever you get podcasts. And keep scrolling to find out what we think are the most valuable takeaways from today’s episode.
— Nate Bagley, Producer of Culture Creators
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Aaron Skonnard ran Pluralsight for twenty years. He took the company from a four-person startup to a Nasdaq IPO and a $3.5 billion exit. Through every milestone and pivot.
Anita Grantham (host of the Culture Creators show) was his CHRO — which makes today’s episode the closest thing on the internet to an operating manual for the ideal CEO/CHRO partnership.
We pulled 6 rules from this conversation with the goal of giving you clear, strategic and tactical insights to help you lead a high-performing team that blows expectations out of the water.
1. The Coachability Test
During her job interview to become Pluralsight’s firstr CHRO, Anita asked Aaron, “Are you willing to be coached?”
The question took him off guard and made him reconsider what he was looking for in a CHRO.
“[It] helped me think more deeply about what I really wanted in this partnership — like, what does the ideal partnership look like? […] I remember thinking, ‘This is the kind of person who really is thinking strategically about how HR will help create and materialize this vision that I have for the company, and that I was so passionate about and committed to.’
It was in that moment that I realized that’s what I really wanted. […]
At first I thought I wanted what everyone wanted — someone who knows HR, who has experience, who knows the drill.
But after going through that dialogue with you, I realized, Ok, with Anita, I’m gonnna get something much deeper, something more strategic, where I can have this deep trust and a true business partner. […] Someone who will, in many way, be my most trusted advisor in the business. That will help me realize a lot of these amazing ideas I have in my head.”
Aaron understood that if he wasn't willing to be coached, he couldn’t expect to create a culture of learning.
The strategic logic: a coachable CEO is the ceiling for what your executive coaching program can do. If the CEO sits out, the team reads the silence and will not go all-in on their own development.
The question is also a leadership test in itself. Coachability is a public statement that there is something to learn, and that you can learn it from people who report to you.
The first move: when you're evaluating your current CEO, or interviewing for your next CHRO role, ask the question plainly. Watch the first three seconds of the answer.
2. Vision Before Culture
A vision is not a sentence on a wall. The Pluralsight vision was a multi-page document that mapped every part of the business five years out, function by function.
"The best culture in the world isn't going to get you anywhere if you don't have a North Star." [00:14:53]
The strategic logic: culture investments without a destination produce activity, not progress. Engagement scores improve. Recognition goes up. Nothing in the business changes. The vision is what gives the culture work somewhere to point.
The first move: write the five-year picture for at least four functions (product, sales, customer, finance) and pressure-test it with your executive team before you green-light the next engagement initiative.
3. Coaching at Every C-Suite Seat
Every C-level executive had a weekly coach. The CEO went first. The whole team rose to that bar. "The whole team just started operating at a higher level every week."
The strategic logic: honest feedback compounds. Once it becomes the operating cadence, the cracks in the executive team get repaired before they become flight risks. Speed comes from the absence of unresolved tension, not from shorter meetings.
The first move: pair the CEO with a coach first. Six months later, extend the program to the C-suite. The right window to introduce coaching at scale is before the team's habits ossify, somewhere between fifty employees and a few hundred. Past that, retrofitting is much harder.
4. Confidentiality Is the Whole Asset
The CHRO has to be a peer to the C-suite and an advisor to the CEO at the same time. The only thing that makes that work is iron-clad confidentiality both directions. This was a clear, agreed-upon expectation between Executives:
We had strict rules around privacy and confidentiality that we would never break.
We wrote that down and said like, these are our rules of engagement and how we wanna operate as a team. And so it was like top of mind for everybody.
We had little sort of phrases we would use to kind of describe the behaviors we
The strategic logic: peer trust is the CHRO's entire asset. Without it, the executive team is polite to you and tells you nothing that matters. The CHRO who breaks the rule becomes a back-channel instead of an advisor, and never gets back to being an advisor.
The first move: write the confidentiality rule down. Brief your CEO on it before you take the job. When an executive shares something in confidence and the issue is strategically consequential, encourage them to bring it to the CEO directly. If they won't, signal the CEO that something is coming without revealing the source.
5. Earn Credibility Outside HR
Anita asked the head of product to teach her how he built a product. She had dinner with the CFO before board meetings to walk through the spreadsheets. She didn't earn her seat by being good at HR. She earned it by being good at the business.
The strategic logic: every other rule in this playbook assumes the CHRO can hold their own in a strategy conversation. That fluency comes from product, finance, and customer time, not from HR certifications.
The first move: book two hours with a non-HR function leader this month and ask them to teach you how their function actually works. The ask itself builds the relationship.
6. Get In Before They Quit
"When an executive gets frustrated to the point that they wanna leave, most of the time it's too late." [00:48:50]
The strategic logic: the retention asset is the relationship. Comp counters at the resignation almost never work because the executive has already mentally left. The CHRO who saves a high-flight-risk executive does it in the small frustrations, months earlier, in the unstructured 1:1s nobody puts on the calendar.
The first move: identify the executive on your team least likely to tell you they're frustrated. Schedule unstructured time with them this month. Not a performance check-in. A conversation.
And underneath all six, the CEO mindset that makes them possible: "I actually am the problem."
If you're carrying the people function at a 100 to 2,000 person company and your CEO keeps you at arm's length, this episode is the case for the partnership you actually want. If you're a CEO who treats the CHRO as a support function, it's the case for the advisor you actually need.
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"I used to think, oh, I'm not the problem. Everyone else is the problem. And then through my own self-development, I started to realize, no, I actually am the problem. I'm a big reason why we're not performing at a higher level. And if I work on myself, that's gonna do more for the company than almost anything else."
That isn’t a pedantic self-help quote. It’s the mark of a leader who knows that the success of his company hinges on his ability to address his own limitations.
Beause it makes him a better leader
Because it sets the example of how he expects others to show up if they want to be part of his team
If the CEO (and the CHRO) doesn’t have the humility to say that line honestly, their partnership is limited.