Why This $3.5B Founder Made His CHRO His Most Trusted Advisor

This transcript has been generated by AI and may contain slight discrepancies from the audio or video recording.

Anita Grantham: Hi Aaron. Thank you so much for coming on our show today. I'm so excited to talk with you.

Aaron Skonnard: Happy to be here.

Anita Grantham: You have been the best CEO partner I've ever had as a CHRO, and I think we did a lot of things that would be great to share with everybody else. I'd love to hear from you, how do you look at the role and how did you define the role when you went out to find the role I eventually filled?

Aaron Skonnard: Thanks for having me here today, I'm excited to talk about all this. You were the first CHRO I hired. Prior to that we didn't really have what I would think of as a real HR department. In a lot of ways when you came to Pluralsight, it was the moment of creation of what we think of as HR today and a people organization.

I think back on it very fondly because for both of us, we were stepping into new territory. For you it was coming to this really fast growth, exciting tech company that was changing the world through e-learning, bringing tech skills to the world. You didn't know a lot about that at the time, and I also didn't know a lot about HR. So coming together, we were really partnering to lay this new foundation for the company.

I remember during the interview process with you, trying to find the right person for this role. You said some things to me and asked me some questions that really helped me think more deeply about what I really wanted in this partnership. One of the things I remember you saying was describing the kind of partnership you wanted to have with the CEO, and testing me to see if I was willing to give that and if I would trust you in that way.

I remember you asking me some very pointed questions around all of that. 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 had for the company and that I was so passionate about and committed to. In that moment I realized that's really what I wanted.

In the interview, at first I just thought I wanted what everyone wanted. Someone who knows HR, who has experience, who kind of knows the drill. But after going through that dialogue with you, I realized with Anita, I'm gonna get something much deeper, something more strategic, where I can have this deep trust and a true business partner. Someone who will in many ways be my partner, my maybe most trusted advisor in the business that will help me realize a lot of these amazing ideas that I have in my head.

That's really what I think is most impactful about the best CEO-CHRO relationships I've seen, like the one I experienced with you, but also when I look around and see other CEOs who are really thriving. They usually have that type of relationship with their head of HR, head of people. That's where amazing things happen.

Anita Grantham: What do you think it was about you that was going to be open to creating that mutual trust?

Aaron Skonnard: I think part of it might have been the fact that I didn't really know. So I was open-minded about it. I've actually seen this in a lot of CEOs too, who have had maybe bad experiences in the past and maybe don't want that. They actually kind of push it away a little bit because they don't want to get too close to anyone in their C-suite. Maybe because of past experiences, they have these biases and their mind isn't willing to go there.

With me, because I hadn't done it before and I didn't really know what great looked like, I was very malleable and open to thinking outside the box of what I really wanted to have in that partnership. I also knew that I wanted the idea of having a close advisor and a close partner, especially around managing a team of really high performing, high potential executives. That was really appealing to me too.

There's a lot to like about that idea, being able to sort of grow this team and create almost like a supply chain of excellence within the business. I think some of it was you bringing me those ideas combined with my growth mindset of what's possible and wanting to learn and wanting to experiment. That allowed us to have a pretty magical moment together in our chapter at Pluralsight.

Anita Grantham: It was a great chapter. Talk a little bit more about the supply chain idea.

Aaron Skonnard: Something I really believe in, we talked about this a lot at Pluralsight with our customers because the product we were delivering to them really promised to give them this supply chain for tech skills in their business. All these new tech innovations are coming out and you can't just rely on going out to hire it all the time when you need it. You need to be able to build an engine within the company to create that future supply of those new emerging skills.

We looked at Pluralsight that way in terms of leadership. We felt like it was our job, you and I in this partnership, CEO-CHRO, to build a supply chain of leadership talent within the business. It was really focused on leadership development. How do we ensure that we're not relying on just going to hire the next kind of leader we need, but instead we're growing these leaders, we're developing these leaders and we're strategically preparing them for the next step in their careers, but also the next step of what the company needs.

We did a ton of work around that. That's what I mean by supply chain.

Anita Grantham: We did a lot of work on our own because we were still in our biggest jobs together. What were some of the things that you remember about how we pushed ourselves to grow with the business?

Aaron Skonnard: I remember one of the questions you asked me, which I think a lot of CEOs might find abrasive. You asked me, are you willing to be coached? I think that was one of the questions you asked me when I was interviewing you.

I thought about it more and I understood why you were asking the question. Because if I wasn't willing to be coached, how am I gonna create a culture of learning and coaching, especially at the executive ranks, in the C-suite? At that time, I was also feeling the stretch happening. I was being stretched in ways that I hadn't been before and I needed help.

Coupled with your question, your challenge, it felt to me like you were asking the question and if I didn't answer it right, you weren't gonna come.

Anita Grantham: That was the situation.

Aaron Skonnard: One of the biggest things I've always appreciated about you is your willingness to learn. A lot of people say that I'm a lifelong learner, but I was looking for evidence that you really wanted to learn and then not just learn but application. You were one of the best appliers of knowledge to your future state I've ever seen. But I didn't know that at the time.

Aaron Skonnard: So you were testing for that. That makes sense. Asking that question was also evidence to me that this was like a deeper partnership. It would be a more meaningful partnership than I had had before with my executives, and it would be one that would actually help me grow and help me develop as a CEO.

I answered the question yes, I would be willing to be coached and that started our journey. We went to great lengths to make the investments necessary financially as well as with time to do our own work on ourselves and on our partnership as CEO-CHRO. That laid the foundation for that type of coaching culture across the executive team, the C-suite.

Anita Grantham: This is a big part of what I wanted us to share, because I do think it was our commitment to how we were going to work together that was a demonstration to the rest of the team on how we could work and function as a team.

Aaron Skonnard: I saw that same thing. When we went to the executive team not long thereafter and said, hey, are you willing to be coached? They all knew what the right answer was too. Some were more excited about it than others, I would say. But because they saw that commitment in us and hopefully they saw improvements in how the coaching was helping us be better leaders for them, most of the executives on the team were actually learning to be hungry for it. Learning that there would be value coming from it.

They all agreed and we had coaches for every person on the executive team for many, many years. That was like a really interesting journey because I've never been at a company where that was the case before. Where every executive at the C-level had a committed coach that they met with every week. There was like a deep commitment. We spent a lot of money on it.

It was a culture that we had developed where we were getting feedback every week. There were private sessions, but you would go in, talk about what was happening, get immediate feedback, learn how to apply it, how to improve your leadership behaviors and characteristics. The whole team just started operating at a higher level.

Anita Grantham: The whole thing too was like, I would say, oh, I wish Aaron would do this with me. And the coach wouldn't say, well, I'm gonna take that back. He would help me figure out how I would go to you and say, if we did this, it would be really impactful. So we actually sped up our efficiency.

Aaron Skonnard: I agree. I think we all moved a lot faster. We were more honest, more direct. Everyone was able to sit in the discomfort of hearing what was working or what wasn't working in their relationships with other executives or between their teams. That does cause things to speed up, it causes things to move faster. You resolve things more quickly. Nothing festers. It's a very high performing environment to be in, where there's no holds barred.

Everyone's very respectful and kind in their approaches. That's one of the things you learn when dealing with a coach. When you're working with a coach, you learn how people are experiencing you better. You become more in tune with that. Therefore you become a kinder human being in many ways, but also capable of being honest and being direct. That's where a lot of magic happens on a high performing team.

Anita Grantham: It's hard. And it's magic.

Aaron Skonnard: It's magic when it happens. A lot of what happened after you came into the business, we committed to this type of relationship we wanted to have. We basically built this machine, this framework that would allow us to create that type of operating environment for leaders in the business. Once the executive team was all demonstrating it and doing it well, we were then able to take it to the rest of the business.

Anita Grantham: I wanna talk more about that, but I wanna go back to another key work stream that we did at the same time. You talked about it this morning, we figured out where we were gonna go.

Aaron Skonnard: Where we're gonna go with the business. The vision. That is super important because culture, you hear people, you hear a lot of leaders will say, culture eats strategy for lunch or breakfast or whatever meal we're talking about. While there is some truth to that, if you don't have a North star and you don't know where you're going, the best culture in the world isn't going to get you anywhere. You first have to have your North Star pretty well cemented, and then your culture is what accelerates you getting there.

Anita Grantham: This is a piece of work that a lot of founders are missing, but also a lot of CHROs don't see as their job.

Aaron Skonnard: To defining the vision. It probably isn't their job alone. This is another place where our partnership really shined. It's really the job of the CEO to own the vision and ultimately the strategy. That's one of the few things that the CEO can't fully delegate, but with a strong CHRO, you can make that vision so much clearer and more impactful for the business. They should also be part of helping formulate it.

I remember when we launched our first Vision 2020, it's still cemented in my mind. That was a special moment. You were a key part of that in both creating it, helping define it, but also in delivering it and cementing it within the company. That's where the partnership comes together.

I remember that kickoff moment, we both felt like we were delivering this thing into the world, like a newborn. This is the new picture of where this company is going. It was after a lot of work, a lot of time, and the whole company had weighed in too. We got feedback and input all across all functions. It was a labor of love that took a while to cement and then fully deliver. But once it was done, everything changed from that moment on.

There was so much more clarity for people. This vision wasn't just like sometimes people get confused when you say vision, sometimes a vision statement is what people think, which is just maybe a few words or a sentence. This vision was different. It was a clearly articulated multi-page vision of what the company is gonna look like five years from now. That takes a lot more effort.

Anita Grantham: It takes a ton more effort. I mean, we had it by customer, product, culture was a piece, our learners were a piece, revenue, our authors, every piece of the business.

Aaron Skonnard: We dissected every part of the business and said, here's what that's gonna look like five years from now. Here's how these different things are gonna change and evolve. Here's ultimately what that's gonna mean in terms of the top line revenue metrics and customer metrics and customer satisfaction. All those other pieces needed to be outlined as well. People within those functions knew, oh, that's what we're aiming for next. That's what we need to go create and build and materialize.

If we had just done that launch event where we were at that movie theater, we had a few hundred employees there, a bunch more remote, if we had just launched that, articulated it and then went about our work and never did anything again, everyone would've forgotten. They might've captured a few headline things from it. But it takes time for a vision to be cemented within a company culture. That's really the job of a CHRO.

It's to help take that vision all the way through the business. So it's part of how we think, how we operate. Everyone's talking about it, referring to it, thinking more deeply about it. We're reporting on it in town halls, quarterly business reviews. We're measuring ourselves against it. It becomes the backbone of the company. The strategy sessions are all about, okay, how do we get to the next milestone in that vision? What tactics are we gonna use to ensure that happens?

You did a great job of that and your team. I remember we created all these beautiful artifacts. We had a great marketing team, so it was a partnership between people and marketing to bring that vision to life within the company. It wasn't just the vision, but also the values, the cultural values.

We always talk about mission, vision, values and then strategy. Those first three things lay the foundation. Mission and vision is where we're going, what we're doing every day and where we're going in the next five years. Then the values, how we're gonna do it, how we're gonna work as a team. Then the strategy outlines the tactics for how you're gonna make it real, how you're gonna execute. When you have all those pieces working together, it's also magic. That's where the best performing teams operate.

Anita Grantham: The number one question that I get from past Pluralsighters is how can I have that again? Just that piece I think is such a construction for success for organizations, so they know what they're operating inside of. Can you share a little bit about how we did the values?

Aaron Skonnard: I will say on that point, I think part of it was lightning in a bottle. I think we timed things perfectly with where the world was going. We got lucky. But at the same time, we executed well with the luck we had been given with some of these things you're talking about. I think that just magnified what we were able to do.

When we did the values, can I go back to the first set of values real quick? I think this is really interesting. When we created our first three values that the company ever had, my co-founders and I did this. We had this little offsite in Park City and we had a little whiteboard and we said, this seems like the best way to do this. Let's just think about the best people in the company we have today. At the time we probably only had maybe 50 people.

We said, but of those 50, who are the people that we feel just embody the best things about Pluralsight today? Everyone started throwing out names and we just wrote the names on the board. We probably had eight to 10 names on the board of the 50. We all looked at each other and said, we agree. These are the people, this is the face of Pluralsight today. What makes Pluralsight special? It's people like this.

Then we said, okay, so now let's go through each one of these people and let's write the first words that pop into our mind when we think about that person. We wrote two or three words for each of these people. Then we zoomed out and said, okay, what are the themes? What are the themes that we see here? There were three really clear themes that emerged, and we called it truth seekers, entrepreneurs, and eternal optimists. So those became our three values.

The point I want to make is those three values came from our people. First we found people that were passionate about what we were doing, who were willing to take a risk and believe in our mission. As that culture started to gel, we then looked for what is it about these people that we wanna replicate and scale so we don't lose that special thing that we had already built. That helped drive our future hiring for the next many years.

Eventually as we got bigger, we realized that those three core values were still missing some things that we valued.

Anita Grantham: Well, and based off the new vision too.

Aaron Skonnard: Right. So we had more clarity on where we wanted to go and what we needed to get there. We started to notice that we don't have a value that talks about customers, that's important to us. We noticed a few other things too. Some people thought we were almost abusing or hijacking the eternal optimist core value. We struggled a lot with results and optimism.

Anita Grantham: Values and performance.

Aaron Skonnard: People started to twist what we meant by some of our original values a little bit. We realized, okay, these need to evolve a little bit. So then we went through a whole process to revamp the values. This was probably another six or seven years into the business from the first time we had created them. I remember when we sat down to do it, we were both like, this is big. Changing values is not something you do lightly.

Anita Grantham: Anytime somebody asks me, tell me if this is how you see it when I zoom out. You change values when you bring in a new executive team and you go on a new mission.

Aaron Skonnard: I think that's true. You at least need to look at them and see if they are consistent with the people you have, the people you wanna have and any sort of evolution to the culture that you wanna create in the company. The values do drive the culture ultimately.

When we sat down to revamp them, we didn't do that exact same process, but we took a similar approach. We actually gathered a group from within the company, not the founders anymore, but people who we felt again embodied the best pieces of Pluralsight. We actually put them in charge of coming up with the ideas of what the new values should be, representing different functions from across the business, different perspectives, different tenures, different locations.

It became a working group, which was very special. Almost a little out of my hands.

Anita Grantham: How was that for you?

Aaron Skonnard: It did take trust and belief that it would produce the best answer. I believed that. There was still an opportunity for me to opine and I was the final decision maker, so I didn't feel like I would have an issue with one before I was able to discuss it with the group.

Anita Grantham: Just for scaling context, we were about 300 people, about seven locations in the US, about 100 million in ARR.

Aaron Skonnard: That's probably about right. We went through the whole process. It took a minute. It wasn't a fast thing. Went through many iterations and then ultimately ended up landing on a set of five core values that we felt were much more representative of the people we had at the time, but also where we wanted to drive the culture in the future.

It was the first time in my career I had changed the values in partnership with my CHRO, you in this case. What could have been a very scary job to do became a lot easier to accomplish, again, with the right partner in the seat.

Anita Grantham: It was also galvanizing for our executive team.

Aaron Skonnard: Everyone who was part of shaping it became ambassadors of these new values to the rest of the business. When we launched, we actually had them help present and talk about these values. It was no longer like, oh, this is a top down, we're just shoving these new values down your throat. It was more like, these came from our people again. Here's why we're moving in this direction and we're talking about things a little bit differently.

Anita Grantham: Again, back to the growth mindset. If everyone in the business has this growth mindset, it's not as shocking that this would happen. Every business needs to evolve. What worked in one chapter may not work in the next chapter. So you're constantly, if you have that culture in the company, it's easier for everyone to adapt and learn and grow and move with it.

Aaron Skonnard: Then you start seeing the culture evolve in a new direction.

Anita Grantham: So we've established the vision, we've established the values, and that's why we picked coaching as an operationalized mechanism to help us live to the values more effectively. What were some of the things that you and I did in the spirit of all this good context that help us optimize the power of a relationship?

Aaron Skonnard: First and foremost, we had a very tight working rhythm. We spent a lot of time together each week. We were in office together. I would spend more time with you in terms of one-on-one time and strategic thinking about the team, about the people, than I would with any other executive really. I think that's the sign of a really strong talent oriented relationship.

That's what I would encourage CEOs to think about. If you have your CHRO at arm's length, you're kind of missing out on a big opportunity. When you spend that kind of time and invest that time in it, you then start learning things about your team that you probably didn't know and you could know very easily. That's one of the first things I started to benefit from in this tighter than normal relationship. You start understanding things about your executive team that need attention.

Anita Grantham: A few things we would do that are just details that may seem silly, but I think made a big difference. We were always hungry or needed tea at two o'clock. So we had like, and even before we switched buildings, 'cause we weren't always in the same building. I would kind of know your schedule and I knew when I could touch base with you. I'm popping in. How are things going? It would give you a chance to be like, I'm thinking about these things and then I would be able to capture them and go figure them out.

The other thing is I would pop by before you went home for the day. You left at 5:30 like clockwork. I knew if I could catch you at 5:15 we'd be able to offload anything important and then I would have what I needed for the next day. So it was intentional but it was also just kind of ad hoc on when I knew I could catch you. It was also genius 'cause we both had young kids and so we'd be off the clock from 5:30 to 10:30, but we knew if we needed to catch up, we could catch up at 10:30.

Aaron Skonnard: That's exactly right. That was the tight rhythm I was referring to. Then also text and other forms of communication was strong and constant. The other thing that would happen, you weren't just checking in with me to see what I needed, but you were also bringing things to me. So in this little check-in that we're doing, I heard this bubble up through the grapevine.

You were good at protecting privacy, not betraying any trusts in your relationships with other people. But also bringing to my attention things that I needed to be aware of. In many cases, we were able to then proactively cut those issues off at the pass in a very powerful and healthy way for the business that could have otherwise become really big issues.

Anita Grantham: And really big time sucks.

Aaron Skonnard: Huge time sucks. In order to optimize efficiency, I kind of think of those military movies where people are back to back and I feel like we were back to back and my job was to cover your flank and to see the things that were coming at you but not tell you everything. Just the things that were pertinent to the week, the month, the quarter that we were in.

Aaron Skonnard: That's a really important and subtle point here. The trust you had with the other executives was paramount for this whole model to work because if they ever felt like you were betraying them with me, it would not work. It's a very difficult line for CHROs to walk. You have to maintain that trust with your peer group. But at the same time, be able to help your CEO see things that might be coming.

In many situations it would be you encouraging them to come to me. That's the best option. When that worked well then, I would be able to go into those conversations much sooner than would've happened otherwise and be able to handle them. Those situations weren't scary to me because of all the work that we had done and the coaching and where I knew my executives were in their coaching as well. So everyone was operating at a higher level and allowed us to tackle concerns or issues or just different things that would emerge.

But if that can't happen, there's also ways for you to help me prepare for those things that might be coming without betraying trust, without breaking trust. That's where I just have to trust you. I can't have all the information and I'm not gonna have it, but I'm trusting that what you're telling me matters for some reason.

Anita Grantham: Did you feel it was non-emotional? I mean, sometimes it was, but like, this is just what's happening.

Aaron Skonnard: I would say most of the time it was just matter of fact. There's something coming your way that you need to be prepared for. But I can't tell you exactly what it is. But that's helpful. It is helpful.

I just hope, and especially if any of our executives listen to this, I hope they know just how much we respected them and cared about them and their individual success in the business. It was always in that spirit. I think you did a fantastic job of being a great peer to them, but also being a strong support to me in my role. That's the potential, the best case relationship between a CEO and a CHRO in this new world that we operate in.

It can't always happen that way 'cause you need two personalities that want to operate that way and where the chemistry works. But when it does work that way, it can be pretty special.

Anita Grantham: There's three things that I can think of that people can take out of this. Maybe a little bit around our rules. We had strict rules around privacy and confidentiality that we would never break. Same way, if somebody came to me on the executive team and said, you have to keep this in confidence, I would 100 % keep it in confidence. So I think that's really important to note, even if it's something I know you would really want to know, I might say, hey, you need to go spend time with so and so, but I can't guarantee you're gonna get there and I can't tell you. But we mutually respected that.

Aaron Skonnard: A hundred %. Another part of that dynamic too was with the coaches, because some of our coaches all worked for the same group, and so we were also worried about coaches sharing information with each other. So those rules even extended to them. Anything that was shared with you, and obviously most coaches know this, this is coaching 101, but not all organizations though. We were very strict about those rules and especially with our dynamic, with our executives on our team, never violated that. That's what made it work, I think, and why they felt that trust, because they knew it would be hard to hide that if you weren't doing that. It would be very obvious, I think.

Anita Grantham: It also decreased the amount of drama, which was amazing.

Aaron Skonnard: It did.

Anita Grantham: Specifically too, one of the things I took for granted at the time that we worked together, that we created, and I didn't realize how much it mattered to me, is that we always had each other's back on the team. So somebody could go to you and say, Anita's making me crazy and she's doing this and this and this. And you would listen and you would do all of that. And you may or may not bring it to me. It doesn't mean I might not have things to work on. And at the time you'd come and say, hey, really, I think we need to work on these things. And I'd be like, okay. But we had such a relationship that we weren't, we worked to not take it personally. We worked to not create drama around it. We took it as useful. That was our term. This is useful and this will help me be better and deliver on the mission.

Aaron Skonnard: Sometimes as a CEO, it's your job to balance what's being shared. You know more about each executive than they may know, because you spend more time one-on-one as the CEO, there's more shared with you in confidence. So you have a little more insight into the team dynamics at times. Maybe with the exception of the CHRO, if the CHRO is doing their job well.

The CEO definitely has a deeper insight into each personality, what drives them, what motivates them, maybe what some of their flaws are in terms of leadership behaviors. So when something is being shared about another executive and holding to this rule of having each other's back, the CEO shouldn't jump on that bandwagon and say, oh yeah, that's terrible that when Anita does that, I wish you wouldn't do that. That's not healthy.

You would listen and try to really understand what's behind it. Then you would help that person see maybe what they might be doing that's contributing to that behavior from the other person. This is where the coaching comes in. A lot of people are really good at this because you don't shift the attention to another person. You actually focus in on what's behind that for you. What are you doing that's contributing to that? Because that's the only thing you can control.

In a lot of ways CEOs do become, some CEOs don't want to do this at all. But the ones that understand people really well are capable of playing this role where you start almost acting a bit like a coach yourself within the business for your executives, and you learn how to balance these dynamics so you're not betraying different members of your team. But you're helping each person on the team learn how they can perform at their very best. That usually means focusing on yourself. It's not about what everyone else is doing. It's about you. So most of the conversation ends up back on that.

Anita Grantham: But this is hard for leaders in any role. How did you come about that realization?

Aaron Skonnard: I think through my own learning and coaching. In the beginning, before I started doing coaching myself, I used to think, oh, I'm not the problem. Everyone else is the problem. We're not performing as well as we could. It must be everyone else that I've hired. That's the approach a lot of people take. It doesn't work most of the time.

It was through my own self-development that 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. As I went through that own realization of my own self-discovery and self-development, it became easier for me to coach my team on those same principles.

I think that's just human nature. Once you've been through it, it's easier to share it. You also learn a lot when you're being coached by someone else. You learn how you can play that role for other people. So I think there was a lot of that happening within the business, not just at our level. But even further down the ranks, there was a lot of coaching happening throughout the business, just naturally, organically. It was built into our culture.

Anita Grantham: I wanna go deeper on this one thing. One of the things I think also contributed to the amazing nature of our partnership for this extended chapter was how you engaged with the rest of the executive team. This is something I really wanted from you. I wanted to see you doing this. Talk about some of the things you did to nurture those relationships where you could have a relationship of trust. It's one of the things I haven't seen very commonly either out there in the wild. Of all the companies I've invested in, or helped in different ways, I haven't quite seen this happen at the same level that it did during that time. You did some things to gain trust with the team that allowed you to have a purview that most CHROs don't have in their business.

Anita Grantham: I think a big part, I remember two situations explicitly, especially when I first started and our head of product, we all were in the same building together. I remember going up to him and I said, teach me how you build a product. Teach me how you look at learners. Teach me how you look at authors. Teach me about the business. And it opened up this whole world of him and he was a great teacher of him being excited to say, let me show you this. Let me show you this. Let me show you why it matters and how I'm building it.

I started to really understand how we built our product from his perspective, because it is like an art form and appreciation for it. Because I knew that I could not hire the talent he needed unless I could see the vision underneath our big vision 2020 for how the product was actually gonna manifest. I had to have my team understand that to deliver the great talent to him, and also to help him work through really complex things, especially as we grew. As we expanded to other countries, as we had multiple products, as we did these things, I couldn't see it if I didn't understand how we built it.

It was the only way for me to have credibility in those strategy sessions. It wasn't about one upping, but it was like, okay, if we're gonna change the org design, remember we just went rounds and rounds. Are we matrixed or are we single threaded? I don't think I could have weighed in on those things and delivered value unless I spent time and understood how he was building product.

Same for, I remember I was scared to death going into our board meetings with one of the greatest who we both know sitting across the table and asking for compensation and not feeling like I understood the impacts to our balance sheet, what that was gonna look like. I remember sitting down with our CFO and saying, will you have dinner with me? Will you sit and go through the spreadsheets with me? We're gonna stay in the conference room. I'll order in whatever you want. And can you help me prep for all the questions I'm gonna get on these things that I do not feel comfortable answering?

It was that moment. I feel like a lot of people don't want to do that. They don't want to show what they don't know. But I actually got people to get behind me and there's a lot of times where he backed me up and he saved me in questions that I couldn't answer because he knew I couldn't answer. But he was doing me a favor because he knew where my boundaries were on certain topics, but he was also well prepped on these topics so we could be partners together to actually serve you and the rest of the management team in these conversations. So it was team building. But it was through me going in and wanting to learn. It was the learner's mindset at the core.

Aaron Skonnard: That's what I was gonna say. It's the growth mindset that you demonstrated to really understand their business and what made it tick. What made it work and the unique things about Pluralsight and how we were doing things differently in each of their worlds. That bonded them to you in a way that they probably hadn't experienced before with HR leaders because they could tell you really wanted to know.

Anita Grantham: Well, and then I started talking to customers at our big event. And that was amazing too, teach me about it, because they had to rely on the local function for implementation. So selling to the CTO, but relying on this channel to make it successful. And I love that insight.

Aaron Skonnard: Ultimately, from my vantage point, the thing I saw is you had a relationship of trust with each of them that looked a little bit different. It was created probably differently with each of them. They all had very different personalities. Very successful at what they did. But bringing all those personalities together and meshing as a team required that kind of understanding from you to then get the talent machinery to really work in our favor as a team.

What also came from that, which was a bonus or a benefit is if one of these executives ever started feeling discouraged for some reason or unhappy about whatever it might be, it might be compensation related, it might be team dynamics. It might be a concern about the strategy. You were often the first one to hear about it because you had that relationship.

Sometimes in companies, when an executive gets frustrated to the point that they wanna leave, most of the time it's too late. But the CHRO with that kind of relationship has the best opportunity to get in to save that person and to help resolve whatever that issue was if it's resolvable. I've seen that play out in our company at Pluralsight, but also many other big companies.

We tried to hire an executive at one point, if you recall, from another big tech company here in Utah. At the last minute, we thought we had the person, he had signed, he was coming, he was committed, and then their CHRO came in and saved the day and that person didn't come. It was because of that relationship that CHRO had with that individual.

Anita Grantham: And a great learning for us, because we had looked at each other and we said, well, we don't ever wanna be there again. Who do we have to be to never be there?

Aaron Skonnard: That's right. And again, in that company too, there was also a really strong partnership between the CEO and the CHRO. Because the CEO knew that that CHRO had such a strong relationship, he was able to rely on her in this situation to really help accomplish what was best for the business in that case, which was retaining that executive.

It's just fascinating how that dynamic can serve the business so well when it's done well.

Anita Grantham: And you and I also had really quick learning cycles. We would see something and be like, oh, we don't like that. Let's not do that again. And again, it wasn't personal. You could come to me and say, hey, I didn't love how you said that in there. And I'd be like, you're right. That was horrible. And you would just be onto the next. But also I felt like I could share that with you. When you did this, I think it could have been done this way and you would've had this impact. And you'd be like, great, thank you. It wasn't this big emotional thing, just part of how we operated.

Aaron Skonnard: I think that's, again, back to the rules and the playbook we had. We had a really tight executive playbook of how we operated as a team that was really clear to everybody. You had two pages, remember?

Anita Grantham: Yeah, I remember that.

Aaron Skonnard: We wrote that down and said these are our rules of engagement and how we wanna operate as a team. So it was top of mind for everybody. We had little phrases we would use to kind of describe the behaviors we wanted to see. Answer first was one of them. Let's explain that.

One of the things that became frustrating to a lot of us in executive team meetings was them just going too long. Part of the reason why they would go too long is someone would ask a question and then someone would take 10 minutes to answer it. We didn't really need those 10 minutes. We just needed the answer. We don't need to know how you got to the answer. We just want the answer. And if we wanna know more, we'll ask you.

So then we implemented this rule, like after everyone sort of, as we had our offsites and talked about what was working, what wasn't working. This thing emerged as we gotta fix this. As a team, we talked about it and said, let's just develop a new rule. Let's write it down called answer first. So next time a question is asked, even though you might be tempted to give the 10 minute version of the answer, just give the answer in 30 seconds and then if anybody wants to know more, we'll ask for more.

That actually did speed things up. It was actually really, really helpful. It doesn't mean that's the right answer for every team or every organization, but if you're operating with that culture as a team, you'll find your own playbook that works best for you.

Anita Grantham: Well, thank you so much for being here. We're just so grateful. We have a few speed round questions that we'll go through.

Aaron Skonnard: Okay. Let's do it.

Anita Grantham: Okay. So start with Johnny's question. Our last CEO gets to ask you a question. And Johnny C. Johnny C. Taylor, Jr., SHRM-SCP, President & CEO (Taylor), Jr., SHRM Senior Certified Professional (SHRM-SCP), President & CEO's question for you is, what is the biggest failure you experienced and what did you learn?

Aaron Skonnard: There were so many. We had a rollercoaster journey over the 20 years that I ran the company, but I think the biggest one was towards the end of not moving fast enough on AI. We saw it. When it hit the scene, we knew it was gonna be impactful, but I think we were also a bit in denial that it was gonna really change things dramatically.

I think that's always everyone's first instinct, especially when you've built something big. We were sitting on 600 million of revenue and it's like, people are still gonna need to learn. There's still gonna be knowledge transfer, people are gonna need to teach. But I think we all underestimated and me in particular underestimated how fast AI was gonna move. I think that has led to a lot of impact to the organization. I wish we would've moved a little faster earlier.

Still the story hasn't been fully written. What does that look like for Pluralsight longer term? I know the organization is working on that night and day today to be a big player in AI, the future of AI learning. But I wish I would've moved faster on AI and thinking more deeply about AI, how AI changes the way our talent performs within the business, how work gets done.

The future of HR has to be AI centric for sure. And then but also how it changes our product, how it changes our solutions. How it changes the learning experience. If I could get one do over, I would definitely do that one differently.

Anita Grantham: What do you think would've pushed you forward in that moment? You talked about a little bit of denial. Was denial because you're so tech forward. This is a surprise for me to hear.

Aaron Skonnard: I think it was not fully appreciating what it would be capable of doing. I think we all have experienced that at different parts of our lives in different ways. The thing that made Pluralsight a monumental success was the fact that we saw the opportunity when the cloud came together with digital content and low cost microphones and all these ingredients. Now the foundation has been laid where we can build a platform where the world can be our classroom. But it was really the innovation of the internet and cloud computing that made that possible and a lot of other learning companies didn't see it.

I think that's always the innovator's dilemma to use Clay Christensen. It's harder to see it sometimes when you were the last innovator to see the next innovation and how that next innovation might disrupt you. So I think we all fall to that at times. I think also we were in a situation with our capital structure and our investor at the time, our primary investor, where innovation wasn't the top priority.

So even though I wanted to go do some of these things and do some of this experimentation and learning, we weren't able to do that. So it was a confluence of a lot of factors and issues. But again, I think one thing is to be tech centric and tech leaning, but another thing is to actually do it. Tech action. Actually go build. We did have a team doing that inside Pluralsight, but it was a small investment. It wasn't like we're shifting the whole company.

I'll give you a good example here in Utah. A good friend of mine, Eric Ray, who runs Podium, he just posted on LinkedIn this week that they just reached 100 million in ARR in their new AI agent revenue. That is not how they built their business. That's not at all how they built it. So they built a business that got to a certain scale and then at a very critical time when growth was slowing, the markets were changing, AI was hitting, they did a massive pivot to where they said we're going to double triple down on AI.

AI is gonna be the future of our revenue. Now they just hit a major milestone where they're outpacing their core business with AI revenue and have a very promising future for the business for the next who knows how many decades. So that's what I'm talking about. Companies today is a moment of massive change and there's never been more opportunity, more change and evolution that's possible in every industry, every landscape and AI is the technology behind all of it.

Anita Grantham: Amazing.

Aaron Skonnard: So if I have a question for the next person, if I get to ask one, it would be, how are you thinking about AI in the context of HR? Is that gonna look different five years from now, 10 years from now? Should the CHRO own a huge chunk of the AI strategy? Is that a world you envision?

Anita Grantham: I think it's a big part of it. It has to be central to it. In any new investment, think about how we would do headcount plans. I think we have to say it's an investment plan. How is the work going to get done? It could be human, it could be automated, it could be AI, and how do we make it work together? I don't think it's gotta be centered just on humans. It's looking at the job to be done. And how do we go tackle that?

Aaron Skonnard: I like that vision. I think there's a lot of truth to that. Which means the job of a CHRO in the future is gonna look very different. You've gotta know AI. And I don't think people should hire the role unless they know and have ability to hire the technical champion to go get it done. So either it'll be absorbed to the CIO or the CTO, but many HR leaders can evolve and get there too.

Anita Grantham: What's one leadership habit you thought mattered early in your career, but now believe is overrated?

Aaron Skonnard: I would say polished communication skills. Having good communication skills is important as a CEO, but I think authenticity in communication matters more. Being vulnerable. Being real. Not being worried about flubbing a sentence or a word or two. Who cares? Also, just coming out with the message if it's bad news. Being direct and clear and authentic and allowing your team to feel what you're feeling.

I think those are more important. I think a lot of CEOs think, oh, now I'm the spokesperson for the company. I've gotta go out and give all these talks and speeches and yes, you need to get good at that, but it's not as important as people think. I think it's more important to be able to deliver a very real, authentic message to your team.

Anita Grantham: If you could give one message to CEOs and CHROs, what would it be?

Aaron Skonnard: Lean in to each other. I think that's the whole topic of today.

Anita Grantham: Awesome. Thank you.

Aaron Skonnard: You bet. Happy to be here. Great to be with you. Thanks.