Why Great Leaders Are So Rare

Why do so many people dread going to work?

Why are great leaders and great places to work still the exception instead of the rule?

In this episode, Jeff Wells shares the story behind High Achiever and the leadership gap that inspired its creation. Drawing from decades of experience leading organizations ranging from startups to billion-dollar enterprises, Jeff explores what changed in the modern workforce, why leadership development is failing so many organizations, and what happens when institutional knowledge disappears faster than it's being replaced.

The conversation challenges common assumptions about leadership, culture, and performance—and offers a different perspective on why employee engagement, trust, and organizational health continue to decline.

At its core, this episode is about a simple belief:

Poor leaders hurt people. Great leaders change lives.

If you've ever wondered why leadership matters so much—or why so many organizations struggle to get it right—this episode is for you.

What got your revenue here won’t get it where it needs to go next. On the Shoulders of Giants is the podcast from High Achiever
 for founders, executives, revenue leaders, and operators responsible for accelerating growth in complex organizations.

Hosted by Jeff Wells, each episode explores the leadership principles, operating systems, and decision-making frameworks behind scalable, sustainable performance.

We go beyond tactics to help organizations align strategy, execution, and resource allocation through a Revenue Operating System designed for clarity, accountability, and measurable growth.

Subscribe for conversations on:
• Revenue Acceleration
• Leadership & Organizational Design
• B2B Growth Strategy
• Sales & Marketing Alignment
• Executive Decision-Making
• Scaling High-Performance Teams

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Transcript

SPEAKER_01 0:00

Ask yourself the question: why is a great place to work the exception and not the rule? Why is working for a great leader the exception and not the rule? And we think it should be the rule. And so the reason behind a high achiever and the reason behind on the shoulders of giants is really about people. There might be a little dust on the bottle, but don't be fooled because what's inside is wisdom. I'm Jeff Wells, and this is on the shoulders of giants.

SPEAKER_00 0:33

Welcome to the podcast on the shoulders of giants with your primary host, Jeff Wells, and your co-host for this episode, Josh Wells. Jeff is my dad. We're going to talk about a couple of things today. Today's the overview podcast of what this is all about, why we're doing it, the intention behind it, and what you can expect out of the podcast. Growing up, I remember you always saying that the primary role of a leader is to make great decisions. And the reason that leaders don't make great decisions is because they lack the context to do so. I think we would be remiss if we don't start the podcast with a little bit of context on where the podcast came from and the intent behind it. So I know it was birthed out of your business high achiever, but give a little context on why podcast, like how'd you even wind up with the intent behind High Achiever?

SPEAKER_01 1:28

Great. I think the question of why do a podcast is it's an important question they have to answer, specifically because we're not doing a podcast to make a bunch of money. They say there's not a lot of money in podcasting. So that's not the primary motivation. I think the secondary motivation for a lot of people in doing a podcast is to drag traffic to their core business. And while for us at High Achiever, that might be a result of a podcast. That's not the intent of the podcast. The primary intent of the podcast and the reason that we decided to use this forum is really because what we're trying to do is take a lot of what we're doing and share it at scale. Our desire to share it at scale is really rooted in the reason we founded the company to begin with. So if you go back in time in 2018, we founded High Achiever, which is a leadership development company. We coach emerging leaders and startups. And we went into the market based on this premise that we saw a big leadership gap in the marketplace. That was sort of the founding principle around High Achiever in 2018. And that thesis or that premise came out of a company that I was at at the time called Spreadfast, a company in Austin, Texas, that was in the social media management space. And looking back, I actually took that job helping them run the sales organization, really to shore up revenue for the sake of what ultimately the CEO wanted to accomplish was either to IPO or sell the company. And that was the original premise. That's the reason I took the job. I actually thought at the time, I lived in Silicon Valley. And I thought at the time, in looking at that job or the responsibility to that job, it was one of the smallest jobs that I had taken in a long time in my career. And it flew into Texas and I met with the team. And even though the job was small in terms of span of control when I started, I actually fell in love with the people. And to be honest, I mean, full transparency, I wasn't super enamored with the social media management space. I had started a company called Circle Suite that was in this social media management space. And we built a platform and ultimately we grew that company a little bit. I sold it back to an investor and one of my partners. We didn't do anything magnanimous. We didn't create anything of significant value. But I learned a lot about the social media management segment at the time. And in full transparency, I wasn't that excited about it. So it wasn't about the platform. But it flew into Austin and met this team of people that was a young team of people. And the company wasn't necessarily young. The company was, I think, about 10 years old at the time, but they were sort of a poster child in the Austin technology scene for this emerging startup. And so while the company wasn't young, the employee population was young. They were just a younger group of people who had done tremendous work to get the company to the point that it was. Unfortunately, I think Rod, the CEO, who was an amazing CEO, one of the best CEOs I ever worked with, had this recognition that what got the company to where they were at that point in time wasn't going to get the company to the next level. And so he was looking for outside help. And so I flew into Austin, met with the team, and just fell in love with the people. I spent three years there. We we did what Rod wanted to do, right? We restored growth of the company. We grew faster than the market. We improved retention rates by about 14%. And we teed the company up at that time to be purchased by Vista Equity Partners. One of the things I realized really, really early on was the first two weeks of the job, I worked south by Southwest. And that was my introduction to the company. And I was going to commute back and forth from Silicon Valley to Austin. And I'll never forget getting on the plane on the way home after two weeks with the team. Even though my Hispanic control wasn't super vast, I'd historically, in prior functions, I'd run an organization that was a billion foreign revenue with 400 people in the organization. So had come from this big company that was extremely complex and it was a hard job. So my perception coming into Spreadfast was that it wasn't going to be that because it was a much smaller team. After two weeks at South by remembered distinctly getting on the plane and flying home and thinking, uh, this ain't going to be easy. And it wasn't so much that anything in business had radically shifted, but I had this clear recognition that the nature of the workforce or the nature of the team was different. And at the time, I wasn't completely sure what was different about it. But after spending two weeks with the team and in that culture, I did have this recognition that was something that was different.

SPEAKER_00 7:14

And very quickly the nature of the type of business or literally the shift in the market and you or shift in the marketplace in your experience in a more legacy type organization versus then stepping into this high growth, fast-paced startup environment. Is it more the nature of the industry or the nature of actually you think the work the work more shifted at that point in time?

SPEAKER_01 7:41

Yeah, it's such a good question because as I as I thought about it then and I think about it today, I I don't think the nature of the work was radically different, right? It wasn't, hey, we're in the social media management space and something's different about that. Although there were nuances, the work itself wasn't radically different. And I had this clear recognition that all of the first principles that I had learned over the course of my career and used so many times to create really good outcomes in virtually every job that I'd been in wasn't that the first principles had changed. And that was sort of the mystery of this thing, right? It was because it wasn't about those things. Those things were still consistent. And over time best practices, the way it takes to succeed. Yeah. I mean, the fundamentals of business hadn't shifted. The way that we run what we call a revenue operating system in a lot of customer-facing organizations, that revenue operating system, whether it was 20 years ago or today, isn't radically different. It's nuanced, but isn't radically different. What's changed is the things around it. So it's a really good question because my recognition was hey, this isn't about, well, an operating system that's built for purpose for this organization work. The answer to that question was absolutely. That hadn't shifted. But the nature of the workforce had radically shifted. And so if you think about it this way, if you were able to go back to 2016 right now, and you were just on the social channels in 2016, what you would have heard as the dominant theme were sort of the complexity, the tension between generations, right? In 2016, you had for the first time in the history of the workforce, you had five generations in the marketplace. And if you'd listened, which I did, just sort of the way I work, is I'm paying attention, and you listen to the social narrative, and the social narrative was crystal clear. It was millennials are lazy and entitled, Gen X is silent, and boomers are no longer relevant. And that's what dominated the airwaves. The irony of that is that you can't help but have the narrative trickle into the workforce. And so I think what I was beginning to understand early in that role was that something had radically changed. And it was the nature of the workforce, it wasn't the nature of the best way to get business done. And I remember coming to this, forming this very clear perspective. And it was this if ultimately I continue to run this organization that was very multi-generational and full of highly talented younger employees. If I continued to manage to lead that group of people the same way that I historically managed boomers, I would not be relevant in the marketplace. And therefore, I had to learn how to do things a little bit differently in this new workforce to get the results that I was looking for.

SPEAKER_00 11:09

Does that make sense? Yeah, the Gary Mieterchuk talks about all the time. This same premise that everybody thinks our gen, well, in 2016 it was millennials, and then it's Gen X, and then it's or yeah, Gen Z. And it it just goes down the chain where the next generation is just more lazy than your generation. And uh he talked about he's obviously in the social media world, and he talks about it all the time. That it's basically you're an idiot if you think that these kids are lazy, they're just figuring out how to make money in a way more productive way, or talking about attention stand, and he's like, people want to talk about the cell phone, and and we can't we don't have the ability to pay attention for long periods of time. And he's like, dude, people will sit down and binge six seasons of a of a TV show in two days and do nothing else, and they're locked in, and it's not because they don't have an attention span, if you are just literally not good at grabbing their attention.

SPEAKER_01 12:11

Yeah. I think that I think it's so true, right? It's it's funny because what I would say is that even though that was the social narrative and that's what you heard on the social channels, in my experience, there was very little of that that was actually true. I didn't find millennials to be lazy. I did find them to be to not pay attention in a lot of cases, but because of what you just said, we weren't creating anything that was compelling enough to pay attention to. So it wasn't about the millennials, it was about, hey, you've got this boomer leader who has prescriptively managed teams in a very similar fashion for a long, long time. And the reality is, is it served me well. And you had a whole generation of boomers who were still in the marketplace who believed that it served them well, and therefore they're not gonna change. That wasn't me. I believed it served me well, but I also had the realization that if I continue to do what I was doing, it wasn't gonna serve me in the same way it served me historically, and that none of the generational nuances were good or bad, they were just different. And it was my responsibility as a leader to build a bridge into the generational nuances versus calling people up this mountain that built over time and thought was right. But it's so interesting because one of the things that I recognized and I heard a lot in the social narrative for boomers. Here's the irony. You would hear a 55-year-old man who'd spent 35 years in the workforce, who had had tremendous success, has amazing skills. And I'd have a one-on-one coaching conversation with them, and they would tell me that the market is aging them out, that ageism is rampant in the marketplace. And my response would be, you're right. It's always been rampant in the marketplace. There's always been this perspective that a younger employee can't do what an older employee can do. That's the reality of the marketplace. Okay. Definitely, as you have a multi-generational workforce, people are looking at you from an age perspective to say, are they still relevant? But what makes them relevant or not isn't their age. It's the way that they adapt to the changing circumstances in the marketplace. And so my realization was, whoa, this ain't about them. This is about me. I need to shift my perspective and learn to be more effective in a multi-generational workforce.

SPEAKER_00 15:02

So the leadership gap was because you said it all started basically with recognition of the leadership gap in the market and try to go solve that. The leadership gap you're saying he recognizes essentially the inability to adapt to cultural changes. Like we just want we just want to, we did it this way for 20 years and it produced. I mean, you're sharing about Rod saying what got us to where we are today is not going to get us to where we want to be in the future. I mean, it's such a it sounds so simple, you're like, duh, but for 99% of the people, it's it's not actually that obvious. You would think continuing to repeat the same motion will continue to grow at the at the pace you want. But what you're saying is the the leadership gap is literally the inability to adapt to a different environment.

SPEAKER_01 15:51

Yeah, it's huge. That's one piece of it. And I think you bringing up Rod there, it's such a great example. Rod's recognition of that problem and his willingness to make a courageous decision to bring in someone like me from the outside into a culture that is very rooted, right? I mean, everybody knew everybody. People went there and stayed. And by the way, it wasn't just Spreadfast as a company, it was Austin, Texas. So it was, oh, here comes this guy from California into a culture that we already have, and he's an older guy and he's gonna do things differently.

SPEAKER_00 16:36

Well, then you come from a way different space, not even remotely close, and also just a double down on your point culture of the company. They all still work together. There's four pods of them jumping from company to company to company.

SPEAKER_01 16:50

Exactly. Yeah, it's super common. But they had a they had a really unique culture and they were a really tight-knit culture. They had kind of grown up together. So I only say that to say this that makes Rod's decision to make that change courageous. Because he could have taken the path of least resistance and not done that. And there's also risk in it because, in a lot of cases, a lot of these organizations are making decisions like that, but they're bringing in the wrong people. And those wrong people are setting the company back, not forward. So if you fast forward two of the guys that came out of SpreadPass with me, Brandon Baxter and Joseph Rodriguez, were the co-founders of High Achiever. And we founded the company based on this premise that there's a massive leadership gap in the marketplace. And we felt like the work that we did to overcome some of those leadership things at Spread Fast uniquely suited us to go out and start a company that would help other companies solve that.

SPEAKER_00 17:56

Can you can you define the what the leadership get was?

SPEAKER_01 17:59

I mean, I know it's multifaceted. It is. I think there's there's a couple things. So it is the complexity of a multi-generational workforce and the nuances that that creates in terms of how you lead across generational tendencies. It's the inability to view those culturally as good and your tendency to bucket those as bad and not ask the question, how do I manage these tendencies in a way that will get me the best work out of the people that are in the organization? So we're in this transition phase. And think about this at the same time, in parallel to the multi-generational nature of the workforce, what you have is you have a mass exodus of boomers. So you've got all kinds of boomers who are exiting the marketplace, and what they're taking with them is 50 years of institutional knowledge. Hence, best practices are first principles. We joke all the time when we're working with companies, and it's we shouldn't joke about it because it's not funny. But the statement is this first principles have left the building. And the harsh reality is it's nobody's fault except the boomers who have exited the marketplace didn't do a great job of preparing the people who are coming up behind them to be successful. So watch what happens. You get this exodus of boomers who are retiring, who are financially free, who are tired because they worked their fanny off for 30 years. And so they start to leave. And what's happening is it's creating a massive vacuum. With their departure, it's opening up new roles that need to be filled. And so younger people without the experience are getting pulled into positions that carry big titles and big responsibilities. And unfortunately, most of them aren't prepared for those responsibilities. We haven't done a good job of preparing them, teaching them, or passing on the first principles. Oftentimes at High Achiever, what we talk about is we'll run a leadership development course. And immediately people will ask, why do you need a leadership development course? When a quick Google search will give you a million different data points where you can learn how to lead on your own. I mean, just talk to AI, it'll tell you exactly how to be the perfect leader. But here's the challenge: the challenge has never been access to information. The internet has provided on-demand access to information that we can possibly consume with a click of a mouse. The challenge is our ability to sequence and assimilate great information in a way that we can ingest that information and move towards outcomes. So we started High Achiever because we believed we could help leaders fill this vacuum in the marketplace and that newer, younger leaders who were being thrust into positions that quite honestly they weren't ready for. And let me just give you this as an anecdotal thing to consider. When I was coming up in the business, it took 15 to 20 years for you to get to VP. I see people making VP in two and a half years, three years, four years, five years. Information plus experience is knowledge. What was in the marketplace is a whole bunch of information, but very little transformation. It leads to the harsh reality that our workforce is in a Terrible position.

SPEAKER_00 22:01

I guess inexperienced leadership leads to inexperienced reps. That's right. Also then get promoted. It degrades over time, time and time again. That's right.

SPEAKER_01 22:14

And so J. Rod and Baxter and I looked at the market and we thought, hey, there is a tangible leadership gap in the marketplace. We believe our thesis is it's created because of a multi-generational workforce and this vacuum that's been created in the workforce. And that we had spent a little over three years plus the rest of our careers thinking about how to be high achiever leaders. And that we believed we could help companies and help people more importantly within those companies close the leadership gap. And we founded that we founded the company based on this statement. I mean, it's really simple, but it's true. Poor leaders hurt people and great leaders change lives. And we believed we could change the nature of people's lives by helping them close the leadership gap. And that took on the form of coaching companies and individuals around leadership and career development. But I will say this first thing we realized, which is tragic, and it really is sort of a state of the workforce. By the way, if you think our thesis is wrong, you don't have to buy into our thesis. Just go look at workforce studies. Go look at the Gallup studies. The data will show you that the current state of the workforce is in the worst position it's been in in the history of my career. And I know what good looks like because I've worked in companies that were great companies with great leaders. Podcast is called On the Shoulders of Giants because I've had my unfair share of opportunity to ride on the shoulders of giants who have gone before me and who were willing to teach me at times how to fill the gaps in the way I was thinking about business for the sake of delivering way better than average outcomes across the course of my entire career. And so we had this thesis that we could help people rapidly accelerate their progress through the things that we've learned by standing on, in essence, the shoulders of those principles that have come before them. Hence the reason we started High Achiever. Now, if you fast forward to why on the shoulders of giants in the form of a podcast, that same mission focused on bringing those first principles to the marketplace at scale, because we can't work one-on-one with everybody. Make sense?

SPEAKER_00 24:43

Yeah, I got a number of thoughts and questions, but we don't but we don't have that much time. So I'll save us for maybe another another conversation. But I think the the what stands out you said, don't you have to believe our thesis. Anybody who's worked for a great or even a remotely good leader has worked for a remotely bad leader, you know the difference and the idea that I mean this is we spend how many hours a week with these individuals, and I've had leaders that are completely non-existent, and I'm doing my own job, and in a lot of ways that's a blessing. On the other hand, I've had leaders who are all over every single thing I'm doing, which it which I was frustrated with initially, and then you realize it's how I mean what are you gonna be frustrated about? Do you want to be do you want your your do you want to succeed or do you not want to? So I think it's it's really clear. And if you have any questions about the impact of your direct manager specifically, but then also organizational leaders, you obviously haven't worked in a shitty organization. And or you obviously haven't worked for a really great leader. So I think that's that is probably the number one thing. And then the other thing, just in terms of the leadership principles that you guys bring in and the value behind that generational gap, it goes back to this completely separate a whole podcast in and of itself. But the the idea of why, again, coming back to the context of your team, Ryan's sent me an email that he sent to his team at SKO. And it's he's so transparent about what he wants for the team and for himself, and not even remotely in a selfish way, just this is what we're this is what I'm building on the team and what we're looking to create. And so I think a lot of the the gaps you see is a lack of intention behind leadership to do anything but drive revenue and the and I'm saying drive revenue because obviously I'm working a sales org, but it could be across any any level of leadership. You get stuck in the the primary outcome that needs, or the primary result you need to create. And so you forget about everything else, but in the midst of it, you lose the you don't build a story for your team as to why they should show up for all the things that they need to do that ultimately will create the outcomes. And I see it for myself literally every day in the business with Brie and Alex because we just all have different desires, but but all of them can be met through the accomplishment of the end goal we're all driving towards. But if you don't build the story around it for them, it's really hard to get there. It's okay, we need to hit this revenue goal. And if you don't tie that back, Ryan's very big on, I don't want to speak for him, but but the being able to be free for his family and take care of his kid and all that type of stuff. It's very big. And you see it a lot now, the work-life balance stuff. But being able to create some freedom financially or time-bound freedom, and you just miss the the a lot of times, leadership misses the connecting point between we're driving towards this outcome because it's gonna generate X, which will create wrapping it back to the story of why each individual rep actually should care.

SPEAKER_01 28:20

Yeah, great outcomes are a byproduct of great leadership, and great leadership is the development of really good culture. And if you figure out how to lead in a great way, execution will take care of itself. But money is a byproduct of people. Build great people. You build, I mean, I don't worry about money. Why don't I worry about money? Because I care about people, and those two things go hand in hand. And so the reason we launched the podcast is to help people think about that and help people at scale. Get into lives of more people and help people change their lives. Why? Because poor leaders hurt people and great leaders change lives. And that's sort of the mission of what we're doing is we want to change lives. The financial implications are always a byproduct. They're always a byproduct.

SPEAKER_00 29:16

I'm just six minutes left before we need to jump here. Do you want to run through some of the structure of what the podcast is going to look like, what people can expect from a format?

SPEAKER_01 29:27

I think it's great. I think really simple. I think what you'll see from us is sort of a multifaceted podcast. Some things where we'll do shorts, where I may be alone sharing just a concept of first principles or use case that came out of coaching in the prior weeks. My favorite sessions, Josh, are these sessions where you and I, or myself and a co-host, are riffing on a topic. And in essence, there's mutual learnings that come out of the discussions, not only for the people who are listening, but for us. Right. And so I love this forum or this format where we're just riffing on a topic. You'll likely see some live interview, I should say live coaching sessions. We're recording actual coaching sessions that we can bring into the podcast. So you can be a fly on the wall of a coaching session, right? And that's because they're so fluid and real at times that there's just a lot of learnings that come through it. And then ultimately, the primary theme is this on the shoulders of giants, is an interview type session of talking to amazing leaders, high achiever leaders who have gone before you and hearing their story and their journey and learning from them. The best part of my whole career, where my career got accelerated, was because of one-on-one coffees with amazing leaders who are of high character, who had gone before me and are willing to take their time to speak into my life. And my hope is that in these interviews, these people are going to speak into your lives and that you're going to learn. And that's the whole premise. I'm fired up about it. It's this forum, these types of relationships where I want to finish my career. And so it's way less about do we drive traffic or do we make money? And it's much more about how do we help. I think that's a pretty good route. Awesome. That was fun. More to come. Thanks for thanks for co hosting. I'm hoping you'll do this a thousand times in the future.

SPEAKER_00 31:35

Yeah, we'll see how many we can get done this year.

SPEAKER_01 31:39

Okay, peace.