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Meg Crosby and Howard Cleveland co-founded PeopleCap Advisors in 2012 to empower leaders and elevate organizations.

Prior to PeopleCap, Crosby worked as an HR leader for companies of all sizes, including a small tech start-up as a sole HR practitioner, and at Google where she led acquisition integration. Her corporate work, consulting practice, and board experience have established her as an expert in organizational culture, people strategy, and high growth.

Cleveland began his career as a labor and employment attorney, guiding leaders through complex employee issues and fostering cultures of trust. Now a sought-after coach and advisor for leaders spanning five continents, Cleveland is known for his strategic insights, leadership expertise, and intuitive understanding of human dynamics.

 

In this episode, Jason, Meg and Howard discuss:

  • Discover the story behind PeopleCap Advisors and their new book, Running the Gauntlet
  • Key leadership challenges during high-growth phases and how to overcome them
  • Explore six key imperatives for successful high-growth leadership
  • How to develop a "self-replicating talent machine" within an organization
  • The importance of culture in leadership and how to define, demonstrate, and defend it

Key Takeaways:

  • Building a strong foundation for long-term success often stems from leveraging complementary skill sets. Their dynamic partnership highlights how diverse perspectives can enrich leadership strategies and drive growth.
  • As high-growth companies expand, leaders must transition from being generalists to specialists. This evolution requires continuous learning and the ability to adapt one's skills to meet the demands of a more complex organizational structure.
  • Sustainable growth hinges on creating robust systems for hiring, training, and talent development. Implementing consistent practices ensures that successful leadership traits are reproduced throughout the organization, fostering long-term resilience.
  • Letting go of long-time employees who no longer fit the evolving structure is not just necessary but beneficial. This intentional liberation can open new opportunities for both the individual and the organization, fostering alignment and renewed momentum.
  • Effective leaders know that culture is not just established but maintained through intentional actions. Defining, demonstrating, and defending cultural values is essential to preserving accountability and ensuring sustainable progress, even during rapid growth.

“That's one of the great things about having a strong culture. It will attract the right people and repel others. It doesn't mean that the people it repels are bad; it just means they're not a fit for the culture.”

 - Meg Thomas Crosby

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Listen to the podcast here:

 

 

Meg Tomas Crosby & Howard Cleveland- The Six Imperatives of Leadership

Hello and welcome everybody to this episode of The Insight Interviews. I've got two guests for you today. Not one, but we got a two for today. I've got Meg Crosby and Howard Cleveland. Meg and Howard co-founded a company called People Cap Advisors, and gosh, they did that over 10 years ago, and they've got some experience and some things that they do in the people business, the HR side of things that I think you all will find very interesting. They've encapsulated their years of experience in a new book that they wrote that we're for sure going to get tom but without any further ado, Meg and Howard, welcome to the Insight Interviews.

Thank you, Jason. We're happy to be here.

Well, we're pumped. You know, today, as we talk prerecording in Maryland, you all are in Tennessee, and through the magic of the internet and technology, we're together right now, and I'm excited. Through my research I did, I noticed that you all have some frameworks, some things when it comes to human resources, culture, what boards should be asking their CEOs, and just different leadership strategies that I definitely want to dig into, but we have an initial question that we've asked every guest on the Insight Interviews, no matter what their background is, no matter what topic of leadership or whatever it is that we're talking about, we go into and it's really to get us facing in a particular direction, which is this: who or what are each of you grateful for today, as we engage one another?

Oh, wow. I mean, I think I'll kick that off by saying I'm grateful for Howard. I was thinking about this this morning, and Howard and I have worked together for12 to 15 years now, and we've known each other longer than that, but we have complimentary skill sets, very different skill sets, but they work well together, and I think that we wouldn't and couldn't have written this book without each other. We've been just really strong thought partners for each other, and it's just been a great working relationship, so I'm grateful for Howard.

Yeah, it's so interesting, and we're going to get into this, I know. And Howard, I want to hear your answer too, I promise, but the first thing I think about there is founders or CEOs that go it alone versus those that have a partner. And man, it just seems to work out better when you have a partner, and so, yeah, I hear you loud and loud and clear there, Meg. Howard, how about you?

Thank you, Meg, and I'm not entirely sure what I can do with that. Mine was along that line of just being thankful for the village that's come together to really help us do what we do, and the challenges along the way, and the insights and the expertise people have shared with us, and the graciousness in helping us and just pulling together. And so, just having those other pieces in our lives, Meg included, and our clients and the like has really been something I'm grateful for today.

Yeah, it takes a community, right? Like there's no question about it. Well, I'm gonna guess that our listeners, some may know either your names or People Cap, but some may not, and so I'd love for each of you, if you wouldn't mind, just giving a just a couple bullet points about your background and maybe an interesting tidbit or two, and then we're going to get into some stuff today when it comes to people and leadership and in the book and everything else. But Meg, what types of background things would you like people to know about you?

Yeah, sure. I mean, I think for me, I started my career in earnest, really, on Wall Street in the 90s, working for a large investment bank, and that's really how I found my way into HR. I left there and moved out to the West Coast in the 2000s, I joined a startup, and felt like technology was going to be the hallmark of my generation, and I wanted to be a part of it. So, I spent some time with a very typical startup, founded by two guys from Caltech, and it was a wild, high growth time and we had the great fortune of being an early acquisition of Google's. And so, I went to work for Google in their people ops group, pretty early on, and really just had a front row seat for high growth, which was very exciting. Later, I moved back to my hometown and ran into Howard. We started a business together, just trying to elevate people and practices around talent development in organizations, and so through that work, we've spent a lot of time with private equity groups, and I now sit on a few corporate boards, and I now have the boardroom experience and that lens to view things. And so, it's been an exciting, exciting time.

Sounds like it. All the way from a startup acquired by Google to what you're doing now, so very interesting. Howard, how about you?

My background was in employment law and labor relations, and so I was really an on-call resource for leaders when they had employee problems. Most of that focus was, how do you document it? How do you make sure that you get what the problem is committed to writing so you can use that later? Then I started getting involved in more and more labor relations, and we were helping companies that wanted to stay union free, and part of that was figuring out why the union was at the doorstep. As we started digging into that, it was almost a culture issue or loss of trust in leadership. And so, we started looking at the workplace in a different way. And so, then that transformed the way I started looking at employment law. So instead of like, you've brought me six employee issues, what if we looked at the leader? Like, what's the leader's role in all of this, in trying to help develop? And so, my practice really went from documenting to developing employees and helping develop leaders. And so, when Meg and I ran into each other, we're both working helping a nonprofit with some HR issues, and through that experience, we paired up.

Yeah, when you say this, it makes me think of, I can't tell you how many leaders that we have come to Rewire, and it's like, hey, we need you to coach our people. They need help in this, or they need help with that. And so often, Howard and Meg, we’re like, maybe you need some help with some things first, and then we'll talk to your people. Sometimes that's a cold shower for them, but, yeah, I hear you loud and clear when you say that. And so, right now, you all have some specialties, and you've got some frameworks, and let's just talk about the book. I mean, you've got a book coming out as of the time of this recording. It's literally next week, and so by the time this podcast lands in people's ears, the book will be maybe a few weeks or a month already out. And the name of the book is called “Running the Gauntlet”, and the subtitle is proven strategies for high growth leaders. What's the big idea of the book?

Well, I think, to explain the title, we very much believe that a CEO is a person who is running the gauntlet. It's, first and foremost, a very lonely role. In some ways, the person at the top has all of the challenges land on their desk. We believe that they are facing lots of challenges coming from different environments, and those are all constantly changing. You know, every day it's a new and different challenge. I tell a story in the book about or give an analogy. In college, I used to play Mario Brothers Nintendo, and if you recall that game, I am probably dating myself, but if you recall that game, it was all about getting the princess, but there were several different worlds you had to advance through, and in the same way, companies grow, and they evolve through different stages of growth, and each one of those stages requires a different leader. It could be the same person, but that person is going to have to lead with different skills and abilities. And so, there are different challenges coming at them, so we wrote the book and developed the framework to give leaders a picture of these are the challenges, this is the growth that you're going to move through, and you need to consider how you lead and the context of the organization as you move through those. So, that's why we wrote the book.

It really is a gauntlet, Meg, and it makes me think of, and I'm not going to get this story exactly straight, but I've heard leadership be described as when you found a company, maybe you're playing golf or tennis, and then as the company evolves, maybe it's doubles tennis or maybe like basketball, like a small little team, and then as you progress, and if you're fortunate enough to gain employees and people, then it turns into maybe a football team and that type of thing. And that leader of when you're leading yourself in golf versus a small team in basketball or a larger team in football or soccer or whatever, boy, those are very different skills, right? And typically, the leader is like, I just like, you know, constructing blacktop or baking, or running this technology, and now, I got all these people around me. It can be very different skill sets.

I love that. That's a great analogy, and we use something similar. But I love what you said about the CEO starting out as someone who probably comes up with your product or sales and has had some experience, and very rarely do you find a leader whose skill set is organization building, right? What we're saying to folks is it’s great that you have that initial primary skill set, but in order to be the CEO all the way through from startup to IPO, you're going to need to be an organization builder, and that's a very different skill set, and that's really what our book is about. How does a leader build an organization that is scalable and sustainable to weather all the challenges of the gauntlet?

Well, let's just get right into it, because I can't tell you, in fact, the person that I spoke with, I alluded to this prerecording right before y'all, who happened to be from Tennessee as well, and it was a CEO that was very different than a lot of CEOs, where he was already looking down the line to when he wanted his exit to be, and had successors that he was starting to think about and wanted to develop and train and all that. And, man, I'm thinking, this is wonderful. This is somebody who is thinking strategically, who wants to do the right thing by the organization, not just himself, and is thinking forward. And I can't tell you how many leaders that we run into, and you do too, which is why you wrote the book, where there just isn't that foresight. There isn't that strategic thinking and certainly the skill set when you're doing the startup versus, oh yeah, now we're actually we're in position to either scale or look at a potential IPO. That type of thing just very, very different. And so, yeah, what types of things have you come up with that's in the book that helps these leaders?

A lot of our clients are founders and first time CEOs, and so when they're looking forward, they're looking forward as far as they can. And so, when we look at, from our experience in working with clients, being able to see that big picture and being able to expand what they can think about strategically is really helpful but also making order and making some sense out of the chaos. And so, a lot of frustration, a lot of overwhelm that we see, and a lot of, as Meg said, feeling that they're going it alone. And so, very reactionary, feeling like they're getting hit from all directions. And so, as we looked back, we were working with a client in San Francisco, and late one night, we grab some In and Out Burger and a bunch of coffee and Diet Coke and started looking at what their issues were, and realized that in almost every client, the issues that were having the greatest impact fell into six categories. In looking at those, there were six things that founders and new CEOs going through high growth really needed to do, and the first being sharp and focus and really having a crystal vision, not only for the future, like you were saying, but also something that you could align people around. And then the second being, calibrate culture, and the idea of having a culture that was in sync with the strategy, that was calibrated to help the strategy, and not focus just on whether or not it was good or not. And then the third being, strengthen leadership, and both at the CEO level, but also at the executive team level, and building the strategic table out and really strengthening that foundation that would take the organization forward. And then the fourth imperative being elevating talent and thinking about ways to take talent to the next level and level up. And you know, in that, there are three or four things that are really helpful, that somebody can do. And then the fifth imperative of aligned structures, and not only from an organizational chart perspective, and making sure the organization is structured to support all the strategic objectives, but are the systems and processes, do they support the strategy? What you recognize, what you compensate, what you reward, are those structures aligned? And then the last, as an organization gets bigger, it's harder to stay in touch. So, the sixth imperative of amplifying communication, and not just looking at ways to get more communication to a larger organization, but how do you get more communication coming up and multi directional? And so, the six imperatives have really formed the basis of the way that we frame issues and then help leaders think about them.

Man, I listen to all of those, Howard, I'm shaking my head, and I'm like, oh, they're just so good. I mean, where do we jump in? Meg, of the six imperatives, I feel like we just turned a half an hour podcast into a potential six-hour podcast, but we're not gonna do that today, although I feel like we could. I don't know, Meg. Where do you want to jump in on those six imperatives?

Oh, man. I mean, we could jump in on any of them. I'm thinking of a story. We were talking about elevating talent, for example, is one that is near and dear to my heart. I think that's chapter five in the book, but we had a client that was just sitting on top of a volcano in terms of just a company that had a crazy revenue opportunity. They had just taken on investment. They had plenty of capital, they were ready to go, but they had not built out their people processes and people function. So, their inability to add talent and actually scale the organization became the limiting factor, and they were missing their revenue because they didn't have tight recruiting processes or training processes in place. And so, all of their staff members who needed to spend time training new employees weren't getting paid to do that. They were getting paid for their client facing time. And so, the culture and the incentives weren't set up to, and also their capacity wasn't set up to reward them from bringing other people along and getting them up to speed. And so, they did a few things that people normally do in that situation. You know, the first thing they do is they outsource training. They're like, let's find a trainer and let's outsource it, you know? And the reality is, no one can train your people. Your frontline people have to train the others coming up. You have to build in that capacity, and you have to build in the incentive that they'll bring people along. And so, they really had to stop and go back and develop this capacity that we call in the book, as a nod to Laszlo Bock, my former boss at Google, building a self-replicating talent machine. How do you build processes to bring talent into the organization, bring people up to speed quickly, up to productivity quickly, so that you can go after the revenue that's before you and these opportunities? And also so that when people leave, you know, we always say, instead of, we've change get hit by a bus to win the lottery and Move to Tahiti.


Either way, something dramatically changes.

Either way, we all are familiar with someone exiting stage left at a really critical time, who takes a lot of institutional knowledge with them. So, it’s really important to have people coming up who can replace that. So, elevate talent is a lot about building those talent practices so that companies are prepared to scale.

Well, let's dive in on that a little bit. I wrote down what you just said. Self replicating talent machine. I know from running companies myself to the people that we coach, boy, if people could put that in place, that would certainly help even the rest of your imperatives, right? Culture gets better. Their focus gets better, their strategy has the ability to improve there. So yeah, if we were to more than scratch the surface of self-replicating talent machine, what does that look like?


Well, it's really all of your HR processes. So plus, I would say culture and focus, as you mentioned, and strategy is in there with focus. So, I would start with, if we start with focus and strategy, one of the things that we always recommend for businesses that are growing is to put in place a goal setting framework. So how does the organization communicate its vision and direction and KPIs to the rest of the team? Does everybody on the team have their own KPIs? Do we understand the direction we're headed in and where we're going? And is there an accountability structure in place, such that if somebody leaves the organization, someone else can come in and see those goals and know where they're supposed to be heading, right? So sharpening focus is critical to that. Do we have a culture that supports people taking the time and giving people the capacity to interview new candidates? Do they feel like that's an important part of their role? Certainly at Google, a very important part of every employee's role was interviewing, recruiting and training new hires. So, do we have a culture that supports that? And then, you know, then do we have the talent management practices? Do we have people sourcing candidates, referring candidates, bringing candidates into the system? Do we have those processes in place that support that? Do we have those training processes, onboarding? Do we know how to do that in a way that is consistent with our culture and strategy? So to your point, yes, there are a lot of different elements to becoming the goal of self-replicating talent machine, but I think they're worth investing in, certainly in those mid stages of growth.

Sure, sure. The more and more interviews like this that I do one, one common theme that comes up with either the actual leaders that I interview of high growth or successful organizations or people like us, that are in the industry of helping those leaders, this talent acquisition, and the piece of continual training and acquiring the right talent. It comes up more than any other topic, where it is like, get the right people on board, and different people say it in different ways, but hire the best of the best talent, and then let them do their thing. And the definition of do their thing is not only do the job that it is that you hired them to do, but also help with culture, replicate themselves like you're talking about, like, the focus, like, all of these things, the talent the people on your team is, gosh, it can be more important than even the task that you have at hand. If you're building something, or serving people, or whatever it is that that talent piece just tends to be that nothing happens without that it seems like.

Yeah, and you know, when we think about elevating talent, there really three things that are involved in that, and three ways to influence that. You hire, you develop, and then the third is liberate. And one of the things that you know you talked about, there's a lot of focus on hiring, and sometimes it's hiring the best person, the most qualified person, but one of the things that sometimes gets lost is who is the best person for where we are right now? For our culture, for what we need, and it may not be the three-page resume, and the 30 years of experience, and so, really tying that back in. There's a lot you know on that, but one of the areas in high growth that really gets sort of missed as an opportunity is the liberate. And you know that early stage, that close knit group, that loyalty, those relationships, that as the company grows, not everybody evolves. And so, to really level up the talent, sometimes you have to let people go into something that they're going to be better in and that's tough, but it's a critical part to really leveling up and elevating talent.

I would add one, just one thing to that, which is, as businesses scale, when you start with startup, you're hiring generalists. You know, people wear a lot of different hats in the beginning, and then as the company grows, talent becomes more and more specialized. And so, some of the early players, they are wonderful generalists, and they will always be great in an early stage scrappy business, but they may not be people who can specialize. They may end up without a hat. It's kind of like musical chairs, and they end up without a seat, and it's not personal. I think it's important for everybody to have the self-awareness of what stage growth company best fits their skills and abilities. So, it's not personal. It's to say, hey, we've now grown to this point where we would either need you to specialize, which may not be what you want to do, and you might want to self-select out and go do this again somewhere else, or you're a person who can specialize further in a specific area. So, you know, I always tell the story. This was actually at our church, we had an organist who was also the IT guy. And at some point, you're never going to be able to replace that guy, right?

Yeah, that's right.

But, you know, I think everybody understands, as people start to come into the organization, they're getting rid of responsibilities, and eventually you just gotta ask, what is your core responsibility? And not everybody has that.

I love the word liberate when you describe that, because I can't tell you the people that we've helped over the years where it really is the right decision to let this person go, for instance, and there's such consternation, especially if it's somebody that you describe where, gosh, they've been there since the beginning, they're such a loyal soldier, they fly the organization flag high, they're great. It's just, ah, we don't have a need for that anymore. And sometimes the very best thing to do, not just for the organization, but actually that individual, is liberate them to where like you say, Meg, they can go do that somewhere else, with another company, where they can take that generalist thing that they're great at and go help another organization up, or it opens up a different opportunity door that we wouldn't have even thought of unless they were liberated to go find that. So, it's not always this hand wringing thing, like, I don't want to let this person go. I don't know how to do it. I feel bad. There are emotions, there's, you know, whatever, the liberating piece of it, it can be wonderful for all parties, not just like, oh, we have to let this person go to be better for the organization type of thing.

I have funny story. When I was at investment bank, I ran the two-year analyst program, and we never fired anyone, because it was two year program, and by the time you were underperforming, there were only a few months left on the clock. There was a guy who he was, you know, really smart guy, you know, Ivy League grad, comes to work and his boss comes to me and says, we got a problem. This guy is spending all of his time in the corporate gym, he's not doing the work, you're gonna have to let him go. And I just thought, oh my gosh, it was a terrible thing for me. I just was angst ridden,

Sure.

And so we did. We terminated him, and then a few weeks later, or several months later, I was on a plane off the west coast reading my favorite magazine, Vanity Fair, and I'm flipping through. He's now a male model. He never should have been an investment banker. And we liberated him, you know, and I ran into him later, and he said, you fired me, and I said, I know it's probably the best thing that ever happened to you. And he said, it was. I'm now at USC film school, you know? It's like, that was your path. This was not your path.

Yeah, yeah, it’s so true. It's a great illustration. But, yeah, I think of countless stories similar where you think maybe at the time it's the worst thing ever., but it can actually be the best thing ever. Rven today, when I think about, and we won't go, we won't go in this direction, because there's so many conversations around this topic right now of AI, but I think of AI replacing different workers and whatever, that is one way to look at it, but it's also like an opportunity and a liberation to go, okay, what else can we do with the talent that that we have as human beings, or in this task, or whatever? So yeah, I love your take on that liberation. I wasn't even thinking of, when we started this piece of our conversation, and you said liberation, the thing that I was thinking about is you hire whatever the best of the best is for your definition of that particular role, and then you liberate them, you set them free to go do what it is that they want to do. But I like your take on it as well that liberating can just meet a bunch of different things, I guess. Is there anything that we haven't talked about yet in our conversation under this running the gauntlet, strategies for leadership, is there any topic that we haven't hit on yet that we to make sure that we hit on before we end our conversation today?

Sore of the ubiquitous part of all of this is the culture, and it gets a lot of time and a lot of discussion, and it just kind of stays amorphous. You know, we talk to leaders about building a culture, the culture they need, or what culture is going to be effective, and there's often this, yeah, yeah, yeah. But how? What?

Right.

And, you know, thinking through it, you know, there are three things that we think about when we think about the culture, and first is defining it, and just what is it? What do you want? The other is demonstrating it, and part of that's actions, part of it is what systems, but the third is defending it, and really rewarding the things you want to reward, but also holding people accountable when they step out. And a lot of times in high growth, you're moving so fast, and the pressure is so much that if someone's producing or bringing in revenue, what you allow and what you tolerate slips a little. And I think that that's the pieces, as there's so much and so much to react to, and so many pressures in high growth, it's easy for that culture to kind of slip, and so really thinking about not only defining it and demonstrating it but defending it as well.

Yeah, defending it. I don't know why today I'm thinking of a lot of sports analogies with you. I don't know that that's very typical for me, but today it is, and you're making me think of Deion Sanders at Colorado, where like it or not, he's put in place a very specific culture, and boy, they fiercely defend it. Some people may say, to the detriment, I don't know, but I just see that as an example. So, defending the culture.

You know, that's one of the things that's great about having a strong culture. It will attract the right people, and it will repel others. It doesn't mean that the people it repels are bad people, it means that they're not a fit for the culture. If you have a strong culture, you should expect that.

Yeah, well said.

It's not a fit for everyone and that's kind of the point.

That's exactly the point. And not only is it okay, but if you're come one, come all, and Kumbaya and everything's great, I don't know, there may be a culture issue there actually.

It's funny. We work with a lot of businesses, and we'll go in and ask employees, you know, what's the culture here, like? And a lot of people, will say, oh, it's like a family.

Yeah.

That is always a huge red flag for us, because to me, that signals we don't have strong accountability. It's hard for me to get people in my family to do stuff and I don't hold them accountable as well as I might if they were employees, and so while I appreciate that means they may be highly relational, I usually think that there's some work to be done to prove accountability.

Yeah, right on. Families are great, but it's a different dynamic for an organization that is profit driven, or whatever the vision or the mission is of the organization, right? Typically, that's different than what a great family you know would be. And so, yeah, red flag for us, too, Meg. I hear you loud and clear. I have a feeling that people are going to want to find out more about the book, find out more about what it is that you all do. I love the fact that you both have very different backgrounds but have come together to benefit leaders throughout the country. So, if people want to find out more about you both, what People Cap does, or even the book, how do people do that?

They can go to our website and it's just www.peoplecap.com, and we've got the frameworks that we use. We've got a lot of blogs there to share and just download information. We've even got an assessment for the growth spotlight that people can take and just get a bird's eye view of kind of where they may be and what may be coming up.

And you can also follow us on LinkedIn. Our LinkedIn information and our emails and even Calendly links are on our website, so, lots of ways to get in touch or follow us and figure out what we're up to. And you can order the book on Amazon.

Oh, perfect. Well, Meg Crosby, Howard Cleveland, congratulations on the book. Thank you for doing the important work that you're doing and thank you for adding value to our Insight Interviews listenership. I wrote a page worth of notes, which sometimes I think that our podcast is for our listeners, and then days like today, I think selfishly, it's just kind of for me. So, thank you very much for that, and I wish you all the best in the work that you do, and all the best with your book. So, Meg and Howard, thank you so much.

Thank you.

We appreciate it.

Oh, that was so good. Meg Crosby, Howard Cleveland, they gave me such good insights from People Cap. I love the title of their book, and I love the way that they backed it up. “Running the Gauntlet”, proven strategies for high growth leaders, and then they went through their particular strategies, everything to do with focus and culture, strength, elevating talent, making sense out of chaos, aligning structure and amplifying communication. Such really, really good things, and I love the stories that they told to back it up. So, those were my insights, but it doesn't much matter what my insights as the host of the show were, but what really matters listeners is what insights did you have?

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