The Greatest Leadership Lessons from the CEO Whisperer

0:00Our job as leaders, whether we're managers, directors, VPs, or C-level, is to grow people, to grow their skills, to grow their confidence, to grow their connections, very similar to being a parent. This is Right About Now with Ryan Alford, a Radcast Network production. We are the number one business show on the planet with over 1 million downloads a month. Taking the BS out of business for over 6 years and over 400 episodes. You ready to start snapping necks and cashing checks? Well, it starts right about now. Hello and welcome to Right About Now. You know, I don't whisper much myself. My voice kind of booms and carries, but we have a whisperer today of a different kind.

0:46He is the CEO whisperer. He is Cameron Harreld. What's up, Cameron? Hey, Ryan. Good to see you. Appreciate you coming on. I know you are a busy man and, hey, a world traveler. So where are we today, Cameron? Today we're in Kelowna, British Columbia. We've got a bunch of friends that live up here. So my wife and I decided that we would spend some time up in this part of the world. And so, yeah, we're in Kelowna. We'll be here for a month. But we've been in 54 countries in the last 36 months. Jeez. It's really global. That is, hey, is that a bucket list thing? Pardon me? Is it bucket list? Yeah, we're calling it our bucket list dream life.

1:25So we both wrote our bucket list three years ago. We each put 150 things on them. And we're just chasing them down. So, yeah, every week or two we do another big bucket list item, sometimes with friends, sometimes on our own. and often in just different parts of the world. We sold our homes, sold our cars, sold our furniture. I have three long-sleeved shirts. I can tell you my entire wardrobe now. Down to the item. You know, I actually like that. I'll say this. I'm wearing pink today, which is actually – I'm usually black. I'm kind of like Steve Jobs, but, I mean, I don't know. I black T-shirt every day.

1:56I have three black lily lemon, three gray, and three white, all the same type, and I just recycle those every four to five months. Two pair of shorts. Pretty crazy. So what makes you the CEO whisperer, Cameron? I was given that moniker by the publisher of Forbes magazine. So Rich Cargaard has been the publisher of the physical print of Forbes and online for about 20 years now. He has seen me speak about four or five times and gave me the nickname the CEO whisperer because I'm often behind the scenes talking to CEOs of these kind of 50 to 500 person companies. And I've worked behind the scenes with CEOs in 28 countries now, I'm including at the highest level.

2:36I coach the CEO in the second in command of Sprint. I coached a monarchy. They own the country of Qatar. So I coached the royal family on running their groups of companies. So I've always worked behind the scenes teaching the CEO what has to happen and then often working with their COO on how to make it happen. The Sprint name rings a bell to me. I worked on wireless in the ad agency business for about 15 years, launching multiple phones. You know, we kicked Sprint's ass for quite a bit. I was on Verizon Wireless. Yeah, it was Marcelo Claret was the CEO that I coached, and then Jamie Jones was his second in command.

3:13Oh, wow. That throws me back for sure. I mean, I think I've, you know, the operating officer side, you know, of what you've got to – I think about this lens a lot because I own multiple companies, but, like, you have the grand visions of the CEO and you have them wanting to do things. But if you can't operate, you can't do or bring all that to life. Is it really boiled down to that? Yeah, it does. I mean, it was Thomas Edison that said, vision without execution is hallucination. And I think so often entrepreneurs have the kind of trendy visionary title, but the only ones who actually are visionary and can actually make it happen are the ones that can either execute or that they have that operations type person right beside them.

3:58I'll give a crazy example that I've never spoken about. The very first business that Elon Musk built was called Zip2. And in January of 1995, I got a phone call from his brother, Kimball, who had just finished working for me for a summer running a house painting business. And the company that was going to invest in Zip2 would not invest in Elon Musk because he was too visionary, too out of the box, had never done anything. Remember, this is 1995, so it's 29 years ago. So they actually backed Kimball Musk and put all the initial money into Zip2, which was what they sold for$350 million prior to selling PayPal.

4:34So their first company was funded based on the COO experience of Kimball Musk, not on the visionary. You really need to have both parts for anybody to believe in the company, quit their jobs, or to just even scale. So it's safe to say that even Elon Musk, you know, like sometimes the CEO gets all the sort of buzz in the credit. But there's always a number two, right? There's always, it has to be. I just sent Guy Raz a note yesterday. He's the host of the How I Built This podcast. I'll see if I still have my note. But he had an episode on his podcast from the woman who started SmartSweets, kind of the sugarless candies.

5:12Yes. Oh, and he said, you know, every good CEO has a COO. And I just dropped Guy a note again. I've known him for years through the TED conference. And I said, I'm glad you continue to recognize that every good CEO has that second in command. Without it, it's really, really tough because the visionary role is so particular. It's almost like a homeowner who's building their dream home. I need to be able to visualize what my home is going to look like, how it's going to feel, what the cabinetry is going to be like, what the flooring is like. But I don't have to be good at making it happen. I shouldn't be a good electrician or a plumber.

5:43but I should know how to get a contractor, the COO, who can hire all those people, like the leadership team and frontline staff, to make my vision come true. And I think that's where the beauty of the CEO-CLO relationship is. It is. It took me a long time to put that together, but I have figured it out. I just, and it, I don't know, it clicked. Like, I think I knew it, but I didn't. You want to believe that that's, I don't know, again, not even being like a martyr to get it all done, but I think it's difficult somewhat for the CEO to even like sort of get there, like especially early CEOs, but I'm sure the experienced ones and the most successful ones, that eventually clicks.

6:24But do you have to probably, I'm sure your job a lot of times is like getting that to click, right? Well, I run an organization called the COO Alliance. So I have second in command COOs that are members from countries all over the world. my job is working with them to help them balance and become that real yin and yang with their CEO so even in my book called the second in command I talked about how do you find the right person how do you build a relationship with the person and a lot of it starts with understanding yourself as the CEO first where most CEOs go awry in their first couple of hires and trying to hire that second in command regardless of the title is they don't do a deep enough dive on themselves what do I love?

7:02What do I hate? What am I really good at? Or what are my unique abilities? What do I suck at? Or what am I just okay at? What fills me with energy on a day to day? And what drains me? And then how can I hire somebody who can do all the stuff that I hate can do all the stuff that drains me of energy can do all the stuff that I suck at. And they match me in terms of core values, they match me in terms of the scale of the organization, maybe they can bring in more strategic insight or P &L responsibility or autonomy. It's a very different hire than hiring ahead of any other functional area that just has to be good at that area.

7:36This you're hiring your business spouse as well. I love that. I mean, it's like, where were you five years ago for me? But I'm here today and still ready to learn more. The COO Alliance. I know you started this. Talk to me about what it is and how it helps people. Yeah. Well, five years ago, I was whispering in the ears of CEOs that were paying me. Now I'm hearing more of it publicly. All right. Well, I'll go read the old stuff again. I did my cheat notes because I wanted you on the show, but like, I got to go deeper on Cameron. Go deep, figure this stuff out. Yeah. So when I left the organization, 1-800-GOT-JUNK 17 years ago, I was the COO of that business.

8:20And it was the fourth business that I built. And in building those four companies, I noticed that there were lots of organizations, that were there to grow and mentor and give skills and confidence and connections to entrepreneurs. We had YPO, we've got Entrepreneurs Organization, Vistage, Genius Network, Baby Bathwater, GoBundance. There's so many organizations for the entrepreneur to go and learn from each other. And then there's lots of organizations for marketers and engineers. In fact, there's trade associations for virtually everything, but there was nowhere for that second-in-command to go.

8:51So what happened was we kept going to these entrepreneur events and we just didn't fit in. It's very similar to a husband that goes to a baby shower. It's like, you're not supposed to be there. Even in this day and age, it's really there for the women. So even if we're showing up, we just know that we're in the wrong space. COOs are not more operational lensed CEOs. And men are not hairy versions of women. So I created the CEO Alliance as a place for COOs to go without the entrepreneurs there, without the distraction of the visionary, and a space where they can connect with themselves, connect and grow their skills, grow their connections and network of people they can rely on so they're not as alone.

9:34And then also work on shedding that imposter syndrome and the confidence that many COOs and, frankly, many CEOs have as well. Yeah, I love that. Talking to Cameron Herald, the second in command, but the first in our hearts.

9:51Cameron, what, tell me about the makeup of a COO. Like, what does that person look like? Because, you know, as a CEO and very much of a more of a visionary and a dreamer and like, like I recognize again, but what makes them, what makes, what's the makeup? Well, and this is what's so hard about them is it's almost like saying what makes a great wife. What makes a great wife is a female woman who matches the husband that she's marrying. Because my wife would be a horrible wife for lots of other husbands and lots of their wives would be a horrible wife for me. So the COO has to be the good match for the CEO.

10:31Most of my COO Alliance members would be horrible COOs for all the other members of the COO Alliance companies. So what the makeup of the seat, kind of really what your question is, is what's the makeup of a COO for me? Because the common skills that they have are they're good at situational leadership. They're good at building consensus. They're good at fostering debate. They're good at project planning and team building. They're often good at collaboration. But they need to be good at all of the functional areas that they're going to be reporting to them. And that's different on a CEO to CEO basis.

11:10I'll give an example of this. When I was the COO for 1-800-GOT-JUNK, I did not have finance or IT report to me. I had the product development team of IT report to me. I had sales and franchising and corporate operations and the call center and PR and marketing all report into me. And then I have other members of the COO alliance who don't have marketing and they have finance. Or they have legal but they don't have IT. because whatever the CEO is great at, they're going to keep. And in some cases, the COO is very outward facing, like I was, a lot of speaking, PR, marketing, business development.

11:45And then in some cases, they're very inward facing. Even the current COO at 1-800-GOT-JUNK never talks to the media, never does speaking, is a very inward facing process, operations, culture, and strategy COO. So there are these common realities around leadership, but not around the functional areas they need to be strong at because that's the match to the CEO. Love that. And I love the characteristics part because you're right. Like the husband wife thing rang true to me. I've been divorced once and like hopefully never again. But finding that right partner is so crucial and so different depending on the person.

12:22So I love that. But I do think there's something like there's a lack of ego, I think, that gets in the way of most CEOs. because as being willing to be the second in command, you know, I think a lot of times, like we talked about, you know, the CEO might be out in front. But a lot of CEOs that I know, you know, don't let their ego get in the way. It seems to be a common thread. Yeah, very common. COOs tend to be that level five leader that Jim Collins talks about in Good to Great. It's that drive to succeed, but humility. There's no need for most of them to actually be forward-facing. Now, the only time that even I wanted to do it for 1-800-GOT-JUNK was it was good for the brand.

13:07Because I had built other franchise organizations already, we were leveraging off of that credibility. When I had already built out Boyd Auto Body and what became Gerber Auto Collision in the US or College Pro Painters, we were relying on some of that as the reason to buy into or believe in what we were doing. So we were leveraging that. The current COO of Shopify, as an example, as a very outward-facing COO. And then you take the current COO of Facebook, or the past, sorry, Sheryl Sandberg, she was a very inward-facing COO. She never spoke to the media until post-leaving Facebook. Harley Finkelstein from Shopify is always talking to the media because his CEO counterpart, Tobias Luque, is a very inward-facing engineering and process-focused CEO.

13:52You know, for our audience listening, It's, I think there's a, you might think, even myself, like I said, admittedly late, I'm 47 years old. Finding out within yourself, you know, whether you're the idealist creative person and you're the dreamer and you're this, I think there's actually confusion that people have of what, where they belong. Like whether I'm, you know, that process, that operator, that whatever, sometimes what hat they wear. You know what tends to happen for the CEO, you know, the visionary entrepreneur is they're worried if I delegate all this stuff to a second in command, what's my job?

14:39What am I doing if I'm getting rid of all that stuff that used to report to me? And they forget that their role is to be the caretaker of vision, of strategy, of culture, of people, and really to be thinking about board and compliance and kind of the legal stuff as well. Like they really need to be thinking of the whole business more holistically. And if they don't have time to grow people, they don't have time to grow the confidence and skills and connections of their leadership team, they're really missing a huge opportunity. So getting that second in command that can take care of operations and the projects and the times and the people so the CEO can stay in their unique ability zone of genius, frees up their time, but then they often need some coaching and ideas around what does my day entail now, right?

15:22How do I do? And otherwise they start meddling. Good word. Or, you know, seagull management, right? They fly in, they shit all over everybody and they fly away. That's often a bored CEO, right? It's the CEO that doesn't know what their swim lanes are and where to focus their time so they get distracted. Instead of realizing, point out the problem, let the COO take care of that problem. But if the CEO wants to protect their brand and that cultural impact they have as that kind of cultural icon in the business, they can't be the one shitting all over everybody. And the COO can often do it in a much better way.

16:00And then the CEO can make the COO look good while the COO is making the CEO look good. that is wisdom, my friend. If you're listening, that'll be a highlight clip, I can already tell you, because there is so much truth in what you just said that I think it takes experience that you have to really reflect on that, or experience of someone like me, a young CEO that's been through it and seen trying, and I'm not a micromanager, but I think a lot of CEOs do. Like, you know, like they they go out of their lane to try to help, but it doesn't really help. Well, let me give you a sad example right now.

16:39For most entrepreneurial CEOs, they've really never been trained on the pure leadership skills that they actually need to run a team of people. They could be very good at the functional area of their business. Maybe they're great as marketers or they're great as salespeople or they're great with their engineering of the specific product. But I'll ask you a couple of questions as an entrepreneur. How much training have you had on running proper job interviews, like on interviewing and hiring people? You know, minimal. Like I did it, you know, because I worked for a large ad agent. I mean, you know, but very little.

17:12Yeah, so you got some training. And that's usually what's happened is if you're in a company of plus 250 people, you tend to start getting some training from the leadership team or the HR team, right? Yep, got a little bit. When you're in a company of less than 250, have you ever had training on how to run effective meetings? Absolutely not. Or have you had training on situational leadership? Nope. Running one-on-one coaching meetings, which we do every week with our team. So running managing conflict or classroom teaching, like all the skills like time management, project management, delegation.

17:41And with running these businesses and not having those skills, the CEO needs to know, shit, this stuff has to be happening in our company, but I'm never going to be the one to teach it because I don't even know how to do it. I need a CLO that can come in and plug in stuff. I launched a course called Invest in Your Leaders, which covers all of those skills I just rattled off. But a COO has to be the one that's integrating and teaching that stuff inside of the organization. Otherwise, it's just you're herding cats. You're constantly trying to hold people accountable instead of hiring accountable people.

18:13You're trying to clean up messes. You're always frustrated with stuff not being delivered. That's usually an operational sign that the CEO really needs to free up and then work in their unique ability. How does I've always toiled with this, Cameron, like small companies, you know, like I ran 100 person teams in Manhattan and worked for a thousand person agencies. So I experienced exactly what you did. It's almost like it's either my it's either a blessing or a curse sometimes because I got to see the resources and the team like when you have thousands of people or hundreds of people that training, those exercises, those processes, all those things that can get done when you have the resource.

19:01but a lot of small businesses, 10, 15, 20, I'm not like mom and pop to person, but 10, 15, 20. How do we, how do we embrace some of the things that you're talking about with a true small business? The first part is, is creating a mindset that the leader's core job is to grow people, right? So if you're a CEO and you've got five people working for you, if you're an entrepreneurial company, you've got 30 people for you, whatever it is, our job as leaders, whether we're managers, directors, VPs or C-level is to grow people, to grow their skills, to grow their confidence, to grow their connections.

19:36Very similar to being a parent. Our job as a parent, yes, it's to show love to our kids. Yes, it's to be there for them. But it's to give them the skills and the confidence so that they can do all the shit that they need so they can move out of the house one day and become adults. Right? And if you don't teach them how to do laundry and do cooking and do some painting and do some basic car repairs, they're not going to have the confidence to get out of the house at 19 and 20, our great-grandparents were running companies at 14 years old because they had the confidence and the skill set. So our job is to grow the skills and confidence and connections of our people.

20:09So one way to do that is create that mindset in your company. A second way is to put a budget in place. I suggest a minimum of 1 % of their annual compensation or$1 ,000, whatever is greater. So if somebody's getting$120 ,000 a year, put$1 ,200 into a budget to grow them. You could have one person come in and do a speaking event to 15 people. So you got the one person's fee covering over 15. You could have a book club on a monthly basis. You could send out videos for them. You could put people through my Invest in Your Leaders course, which is only$740 a person. So you can do it in lots of ways.

20:46The key is to create that mindset and the budget. And then remember that if you're always trying to grow their skills and confidence and connections, they're going to be able to take on more, which means you can continue to delegate. And that actually buys back your time, scales up the entire organization. Talking with Cameron Herold, he is the second in command author. And look, I know he's a true COO because he's got solutions to every question. I've built a few companies. There's something I don't. If you ask me deep finance questions, I'll take a pass. If you ask me anything about technology, I will bow out.

21:22But if it's on the operations, execution, culture, people, meetings, and even a fair amount around PR and marketing, I'm pretty conversant. What are we doing these days, Cameron? What's your passions like now? I mean, you've had a great career. You've had these successes. You've built the alliance. What are we up to? And what makes your bell ring these days? Well, you know, a big one is that it's a remembrance that none of this shit actually matters, right? I had a very, very close friend of 17 years pass away two days ago. Wow. Yeah, super close friend. We met in the entrepreneurs organization back in 2007.

22:04And when I watch a friend at 45 years old, a father of four little girls, drop dead without having any prior illnesses, you know, losing a couple of family friends. both my parents passing away in the last 20 years, my dad dying 18 months ago, you realize that this is just what we're doing to make money. This isn't a reason for being as a human. So it's about having hobbies and having bucket list items and spending time with friends and family and spending time with kids and spending time with ourselves and remembering that we've got to enjoy the journey. But I think so often people, especially North Americans, one thing I've known or noticed by traveling, my wife and I again sold everything three years ago.

22:41We've been in 54 countries in the last 36 months. When you spend so much time in other parts of the world, you recognize that no other parts of the world spend their entire focus on work. Nobody in Italy says work is my hobby. You know, nobody in Thailand says, oh, you know, I love what I do for work. Like they have freaking hobbies and they take more than six weeks vacation every year. And I think that's been very reinforced to me right now is that I can still grow a successful business by delegating more, by growing people more, by getting stuff off my plate so my team is doing it. And then I give them five weeks paid vacation and I take vacation.

23:17Two years ago, I took 11 weeks vacation. I think that's really becoming more and more reinforced in the last few years is you can actually build a much more successful company by taking time off, by having hobbies, by saying no more, by delegating everything except genius instead of getting caught up in the busy work all the time that we tend to get caught up in. There's your insights, my friends. That's true wisdom. And I am, I did not know, I've heard of John and I didn't even know he's that young. That is just, I mean, I have, I'm a father of four boys and young. I did not know. Yeah. His girls were the same age as your boys.

23:55So like, imagine that today, tonight, when you go see your boys, when like, and you know what? Yeah. Go give every single one of those kids a hug and a big freaking bear hug and drop them to the floor and wrestle with them and tell your wife the same stuff. You know, like it's, I had a friend in an event in Turkey three months ago. He said, at the end of the day, we all end up as kebabs. We're just going to be a meat on sticks, right? And I think we often take everything so seriously and stay so focused on it for no reason. And again, this isn't in the absence of building great companies, but I don't think that we should, we have to remember our employees are showing up with problems and struggles and real life.

24:38And if we care more about them and the humanity of what they're going through, they'll care about our business. Right. When you become that truly empathetic leader and care about people, they work way harder than holding them accountable and managing them and telling them what to do. Thousand percent. Talking with Cameron Herold. Cameron. So what types of people come to you for advice these days? All types. Yeah. There's definitely the clients who come in that typically the mid-sized companies, the 5 million to 50 million or 5 to 100 million that put their second in command into the CO alliance.