The CEO Whisperer’s Advice for Hiring a Second in Command, with Cameron Herold

Announcer: Welcome to The Lawyerist Podcast, a series of discussions with entrepreneurs and innovators about building a successful law practice in today’s challenging and constantly changing legal market. Lawyerist supports attorneys, building client-centered, and future-oriented small law firms through community, content, and coaching both online and through the Lawyerist Lab. And now from the team that brought you The Small Firm Roadmap and your podcast hosts

Sara Muender (00:35):

Hi, I am Sara Muender

Zack Glaser (00:36):

And I’m Zack. And this is episode 476 of the Lawyerist Podcast, part of the Legal Talk Network. Today, Stephanie talks with Cameron Herold about his new book Second in Command.

Sara Muender (00:48):

Today’s podcast is brought to you by  Posh Virtual Receptionists,  NetDocuments  & LawPay. We wouldn’t be able to do the show without their support. Stay tuned, we’ll tell you more about them later on.

Zack Glaser (01:00):

So Sara, I’m a legal tech advisor for Lawyerist Lab and I talk to a lot of people about technology that they use in their practices, but since we have merged with Affinity since the beginning of this year, I guess we have a lot more coaches and lab has, it has not fundamentally looked different, but from my perspective, looking in has looked very different with Amy Grubb and Supriya and Leticia, all of those new coaches. Sometimes I get a little lost, but you’re in there, you’re deep. What’s going on?

Sara Muender (01:33):

I got my lab coat on deep in the experimental process every day. That’s what I do.

Zack Glaser (01:38):

Yeah, so what’s going on? What’s new? What’s up?

Sara Muender (01:41):

Well, for those that aren’t familiar, so the lab program is our business coaching program for solo and small firm owners. And I am a lab coach here. I was the first coach that was hired for lab, second to Stephanie, who’s now doing bigger and better things. For the most part, she still does a little bit of coaching and it’s been so cool to see our lab program grow and become so much more valuable in a lot of ways. And so much of that has to do with people coming into the lab program and bringing their situations and knowledge and experience to other lab members because so much value comes from them getting with each other and helping each other. But I will say that we have such a special group of coaches right now, and as we grow, that will continue to change over time as the nature of business does.

(02:40):

But right now it’s such a magical time because as you said, we’ve had Amy come on within the last year and we’ve had Leticia and Supriya and myself, and we’re all very different coaches. We just have a different style and I hear about of the strategies that the other coaches use, and I’m learning from them and I’m like, Hey, I’m going to use that in my next coaching session. And then for example, we had a new lab member come in and she is someone who happens to just, she wants to know all her options before making a decision and she wanted to meet with all the coaches before deciding who she wanted to be picked with. And that’s a little unusual, although normally people just kind get assigned to a coach based on what they need in their firm and based on the expertise of coaches expertise.

(03:29):

But I really appreciated and respected that she came in and she wanted to meet with all of us. So I got to meet with her today and she had already met with several of the other coaches and it was really cool to hear what value she got from them. And by the end of the call, we just had such a great time. We ended up spending way too much time together because we were going deep into what she’s got going on in her business. And it was a lot of fun and I think that I found a lot of ways to help her moving forward, but she was like, man, you guys make this really hard to choose who to stick with as an ongoing coach. And I just told her, Hey, look, I’d love the opportunity to work with you, but if you end up with someone else, just know that I’m here anytime you want to meet with me.

(04:09):

And so what I love about our lab program is we are all hands-on and we work as a team. I’m not getting commission for the amount of people that I’m coaching, so there’s really no incentive for us to not work as a team. And then she was asking me about the other coaches on the team, and of course I mentioned you how you do legal tech advising. And we have a finance coach and we’ve got Ryan McKean who brings his wealth of experience running from his practice. But we’ve got so many cool things going on in lab this time of year, it’s quarter four. We’re really ramping up to get started for all of our lab members to have a really solid plan for next year, a financial strategy, a marketing strategy, a hiring strategy, and get their ducks in a row. So every quarter we host a quarterly planning retreat, which is where they do a retrospective of the previous quarter and then they make a plan for the following quarter.

(05:01):

But it’s a special time of year now where we’re really honing in on, alright, what are the things that we want to be able to check off the list by the end of this year and what would call this year a success? And then let’s start thinking about the things that we want to start implementing in 2024. So it’s a great time to come in. A lot of people ask me, when’s the best time to get started in lab? And it’s like, well, ideally six months ago, but just come in now and no matter what stage of business that you’re in, we can help you and we can help you develop a plan to get to where you want to go.

Zack Glaser (05:33):

I like that. When’s the best time to plant a tree? 40 years ago. When’s the second best time today? Today. Second best time to join lab today.

Sara Muender (05:43):

People tend to put it off though because they think they’re too busy. And the reality of the situation is there will always be things that come rushing in to fill your time. And I tell people sometimes if you want things to change, if you want things to be different, have to be willing to take a step back so that you can take five steps forward. It’s kind of this idea of slowing down to speed up and it is so worth it to make that kind of investment in your business.

Zack Glaser (06:09):

Love it, love it. All right. Well now here is Stephanie’s conversation with Cameron.

Cameron Herold (06:18):

Hi, I’m Cameron Herold. I’m the founder of the COO Alliance and the author of the Second in Command podcast. And then most recently, my sixth book, the Second in Command. I’ve also done a lot of work over the last 16 years behind the scenes coaching companies in 28 countries, but I’ve also been privileged to coach seven or eight firms that are in the legal space, CEOs that actually run their own law firms and a couple of digital marketing agencies that focus on the legal space. I’ve also got my undergraduate degree in law, which is one of the only undergrad degrees. I have a bachelor’s degree with a law major from Carleton University in Canada. So I can know enough about law to be dangerous. Not enough, a lot to practice, but I love the industry.

Stephanie Everett (06:56):

Awesome, and welcome back to the show. We were so fortunate to have you on when you talked about Vivid Vision and taught us why our vision statements do not need to be a sentence because that’s ridiculous. So I love that and I’m super excited to learn more about this idea of second in command. So maybe you could just give us a little backstory in how you kind of started doing this work.

Cameron Herold (07:19):

It’s interesting. When I was growing up in Canada, my father owned his own company and so did both sets of grandparents. And I grew up in this very entrepreneurial organization. One grandfather owned a hunting and fishing resort and my grandmother was basically his second in command. They were pretty much joined at the hip as a couple, but also in co-running the business with his divide and conquer. My dad running his company had Murray Head. Murray worked for my dad for 35 years as my dad’s second in command. So I was really around it and watching these entrepreneurs that really had these second in commands in their businesses. And then I ended up becoming the second in command two or three times for a couple of different companies. The third company that I really played the defacto COO role for was called the 1-800-GOT-JUNK, and I grew them from 14 employees to 3,100 employees in six years.

(08:07):

And then because of being in that space, I started getting asked to talk about how do companies grow, how do they scale? And I always saw it from an operational perspective, so I just had a very unique insight into that COO role started the COO Alliance six and a half years ago, started the Second Command podcast five years ago, and I’ve interviewed 320 COOs. So I just have this unique experience and understanding. What tends to happen is entrepreneurs tend to be very good at a few areas of their business and they tend to suck at or be bad at a few other areas of the business. And that tends to be the first second in command they bring into the organization is someone to pick up the pieces and assist them in the areas they’re not good at, which really helps supercharge the organization and help it scale.

Stephanie Everett (08:51):

One thing that really was noticeable to me is really just even idea of calling this role second in command because I think a lot of times we’ve traditionally thought about CEO and COO and it seems like you take a different approach about really the strengths of the people. And so I’d love to hear a little bit more about that.

Cameron Herold (09:12):

That was something that came to me again very early on in business that we had a head of finance, but we didn’t call them a CFO originally. We called them a director of finance. And then over the years, as they began to have more power and responsibility, more decision-making, they started bringing a level of strategy into the business. They were able to operate and build the finance area with a level of autonomy they didn’t need to be managed and overseen. So they kind of moved from the director of finance into a VP of finance, and then eventually after five years, we replaced them with a true CFO who brought a huge level of strategy and management experience into the organization. So I started getting frustrated when I was hearing clients and seeing entrepreneurs call their second in command a COO, and they were only paying them 140,000 a year.

(10:01):

I mean that’s really a director of operations or an operations manager with a big title. So the reason I called my book, the second in command was to partially help educate people what level of second in command you have, is it an operations manager? Heck, maybe it’s an executive assistant or a chief of staff or a general manager or a director of ops or VP ops or a COO. And that true second in command can have a different title based on the amount of money you’re paying them based on the amount of strategy they bring into the business based on the amount of P and I responsibility they have based on the amount of management time you need to give them or don’t need to give them, and the amount of experience that they can bring from their past into the organization that should determine the title that you’re willing to pay someone. And then lastly, on this, 30 years ago to get a COO title or a CFO title or a chief marketing officer title, you had to be a major player in a major company and we’ve had a lot of title inflation over the years, which ends up costing entrepreneurs a lot of money. So that’s why I titled the book that and why that’s part of what the book the second in command is about is understanding that.

Stephanie Everett (11:09):

Yeah. So for our small business owners out there, how do they know what a second in command does or should do? How do you start thinking about that role for your company?

Cameron Herold (11:23):

It’s really whatever the parts of the business that you are not good at as an entrepreneur, what would you bring into the organization? So let’s say that you’re a very tech savvy COO or a CEO, very tech savvy entrepreneur. You might need a second in command who comes in that is more sales and marketing focused, more culture focused, more operations are people focused. If you tend to be a very good sales and marketing leader as an entrepreneur, you probably need a second in command who doesn’t want to manage those areas, but make counterbalance whatever you are great at and whatever feeds you with energy, you’re going to want to bring a second in command in your organization that handles all the areas that drain you of energy and that manages all the areas that you’re not good at. You could actually even be the head of a law firm, but maybe law really isn’t your strength.

(12:11):

Maybe you kind of got your way through law, but you don’t really love law. Maybe you actually like the sales and marketing, you like being the thought leader, you like being a spokesperson for the law firm and you might have a COO who really does have a big law experience or legal background, or you could have a COO who has no legal background whatsoever, but they’re great at managing the operation side of the business. It’s a confusing role. And actually Harvard Business Review wrote an article 16 years ago called The Misunderstood Role of the COO. And again, I talk a little bit about that in my book, The Second in Command as well.

Stephanie Everett (12:44):

Yeah, I think that helps because I do think when I first picked up your book, I entered it with an assumption that I knew what a COO should do and you quickly taught me a different thing. Like, no, you need a person. This is a role that needs to pick up the pieces where the entrepreneur’s leaving off that really resonated with me. I think even a lot of law firm owners get stuck in their head around what does this role need to be?

Cameron Herold (13:13):

Well, and it also has to match the season that your company is in or the stage of growth that your company is in. If you’re a small law firm with 4 to 10 people working in your firm, you need a very different second in command than someone like Seth Bader from Bader Scott that has 200 employees where he’s got Luis Scott as his second in command and they’re running a very big professional services organization with lots of moving parts. So I would’ve been probably a horrible, even though I was an amazing second in command for 1-800-GOT-JUNK, I would be horrible as the COO for that company today because now it’s 450 million in revenue. When I left the company, it was a hundred million in revenue. So it depends on the season as well. You need to look for someone who is, if you’re a smaller firm, someone who’s very entrepreneurial, someone who maybe is more of a jack of all trades, a master of none, someone who can move quickly and think quickly, but if you’re a much bigger, if you’re kind of in the a hundred to 300 person phase, you need someone who’s more strategic, who’s more matrix decision-making, who’s going to slow it down and be more inclusive.

(14:19):

So it again is something you have to consider on who you’re bringing in as your second in command.

Stephanie Everett (14:24):

When you think about timing, a lot of the lawyers listening probably started their own business. They’ve added to the team over time. They’re listening to this and they’re like, ah, am I ready for this role? I’m kind of curious now. How would you answer that when you’re ready or yeah, when is somebody ready for this role?

Cameron Herold (14:44):

One of the big flags is when you realize as the entrepreneur, as the CEO of a company that you have no time to grow people. At best, you’re kind of managing them quickly. You got 15 minutes a week for somebody. Well, that’s not actually growing them. It’s not removing obstacles, it’s not growing their competency. It’s not helping them scale. It’s not delegating more and more business responsibility to them because you’re so busy kind of on that hamster wheel. So that’s one reason. A second reason is when you have no life, right? When you’re literally immersed in the business and you’re having to work constantly and you have no time for your spouse or your children or your hobbies or yourself, then really freeing up time because we only start a firm for one of three reasons, to give us money, to give us free time or to be able to put a flag or a stake in the ground to say that we accomplished it, right, we did it.

(15:35):

But once you’re up and running, you’ve done it. And once you’ve got enough cash coming in, you’ve got it, but it’s the time is another element. And then thirdly is an opportunity when you realize you’re working in areas of the business that drain you of energy and you’re not good at, and if you had that second in command to oversee those areas for you, you’d probably get an incremental ROI that maybe you’re paying them $250,000 a year to be a true COO, but now you’re actually getting millions of dollars of incremental revenue, more free time. The people are happier, your clients are happier. So it’s for those reasons that you’ll do it as well.

Stephanie Everett (16:09):

That’s super helpful. Let’s take a quick break here from our sponsors. When we come back, I want to shift a little bit more into this second in command role.

Zack Glaser:

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Stephanie Everett (18:37):

So I’m back with Cameron, and we’re talking about the second in command for your business, and I’m curious to know, what do you think that entrepreneurs need to do that will set this person up for the most success in the business?

Cameron Herold (18:52):

Yeah, it’s interesting. When I was building out a chain of auto body collision repair shops, this was before 1-800-GOT-JUNK. It’s now called Gerber Auto Collision in the United States and Boyd Auto Body in Canada. I said to the CEO one day, I need to have a weekly call with you so that you and I can stay in sync and talk through the business. He goes, no, I don’t need that. You’ve got it. You’ve done this before. It’s easy for you. You can just run with it. Call me as you need me. I said, no, no, I need this time. It was kind of like, I need date night. I need time away from the kids. It was me asking for what I needed as that second in command. So one of the things that the entrepreneur can do to set the second in command up for success is to build in time into your calendar to have a one-on-one time with them to talk about the business, to talk about strategy, to talk about the plans to communicate vision, to talk about what you have.

(19:43):

Secondly, it’s to have time with your second in command out of the business where you can work together offsite from your golf club, from a tennis club, from a hotel, from an Airbnb where you just have hobbies together. You go golfing together, you play tennis together, you go for hikes together, whatever it is where you can get away from the business and again, away from the rest of the leadership team. It’s very, very important that you also work on the trust and communication. I actually have a marriage counselor who does marriage counseling for high performance Wall Street executives and their spouses. She actually has done a lot of work for CEOs and their COOs to help them build communication and trust systems in place. So it’s really important to get to understand the other person and get them to understand you. It’s almost like if each of you wrote a two-page operating manual to yourself, if you’re William Mattar and you’re the CEO of a law firm, how does Bill tick?

(20:36):

Right? What does he, how does he like to be talked to? How does he like meetings to run? What drives him crazy? What gets him excited? How does he review data? And if will Bill Mattar shared that with his second command and the second commander wrote a manual for himself and shared that with Bill, that would help both of them get in sync very quickly. So that’s a third thing that you can do is write a two page operating manual for what makes you tick and share that with your COO as well and have them do it with you.

Stephanie Everett (21:03):

Yeah, that’s super helpful. I imagine that a lot of people might get this wrong their first go around. I was just having a conversation with someone and she’s noticed that a lot of law firms kind of hire the wrong first person and then say, well, that didn’t work, done with that experiment. And it’s like, well, maybe you just didn’t have the right person or the right doesn’t mean you should give up on it.

Cameron Herold (21:26):

Well, here’s the analogy of this, and this will make sense for every lawyer, every business person has written up their own contract or written up their own kind of agreement, and they’ve ended up screwing things up because they’re not a lawyer. Well, I have not found a lawyer yet that when they went through law school, studied interviewing and hiring and onboarding and the growing of people, it was never included in the legal curriculum. We had to study contract law and private and banking and import export and all employment, but none of us ever studied actually running a company. So of course you suck at it. It’s really hard for you to go out and interview and hire people if you’ve had no training on interviewing and hiring people. In fact, one of the things that I launched two years ago that every firm, every law firm or manager in a law firm should go through is my Invest in Your Leaders course.

(22:15):

It’s called Invest in Your leaders.com, and it has 12 core modules that if a lawyer went through those, they would actually be much more competent at running a business. So it’s things like situational leadership, coaching, interviewing, running effective meetings, delegation, time management, project management, managing conflict. I lay out the 12 core leadership skills, but that’s why most law firms make mistakes on hiring people is they’ve never been trained on interviewing. I asked the CEO about three months ago, have you ever had any training on interviewing? And he said, no, but I’ve interviewed a hundred people, and I said, maybe you’ve done it wrong every single time. And he went, oh my gosh, you’re right. It had never dawned on him, but just because he’d done it a hundred times, maybe he’d done it wrong a hundred times. And I think that’s where if we would actually get some skill development on those core areas of the business, business gets very simple very quickly.

Stephanie Everett (23:10):

I’m a big fan of that. I did an interview training for a law firm last week and I preached the same message, so no arguments there.

Cameron Herold (23:20):

I was sitting on a plane one time and I was reading through a contract on a plane one time and it was written in French, and I studied French and university as well as law, but I only got through intermediate French. So I’m sitting reading at a legal agreement in French, and it’s written in French civil code. I’m like, what am I doing? I have no business reviewing this contract. And that’s kind of like if I had the skills, then I can do it, but get yourself the skills.

Stephanie Everett (23:45):

Yeah, love that. A lot of people listening are probably familiar with Traction, the book by Gina Wickman, and some of the principles he lays out are around this idea of a visionary and integrator. And I’m curious how your ideas of second in command line up or even maybe differ from that framework.

Cameron Herold (24:07):

The framework is very good. I mean, it doesn’t get into how to hire one, how to interview one, what their first 90 days are like, how to build communication. So even if we run on the assumption that the visionary integrator model is perfect in and of itself, like visionary being CEO integrator, being second in command, you still need all of the content. In my book, and I know Gino very well, we’re in a couple of mastermind, we’re in three different mastermind communities together, genius Network, strategic Coach, and Abundance 360. So I know him well. I know his content really well. The one area that we differ on, the visionary integrator is he says, the integrator is to be the tiebreaker. Well, the tiebreaker is almost like your mom or dad saying, because I said so or because I’m your mother. Well, that works until we’re seven or eight years old, and then all of a sudden we’re like, wait, I’m not taking that as the reason.

(24:58):

Imagine your mom saying to you today, Stephanie, because I’m your mother. You’d be like, well, I’m an adult too, mom, you can’t be the tiebreaker forever. So once your company has a management team of managers or leaders that are competent that have run businesses before, they don’t want the integrator or the COO or that second command to be the tiebreaker. They want someone to teach them how to have good debate, how to get to consensus on their own as a team, how to argue, how to deal with conflict, how to look at the data, how to bring in the facts and feelings and how as a team to come to consensus versus saying, okay, three, say this. Three say that I’m the tiebreaker. I say this. So that’s where I differ very quickly is once your management team has a level of experience, you don’t need a tiebreaker at all. You need a true second in command.

Stephanie Everett (25:45):

Makes sense. I guess, too, I’m curious, and maybe it doesn’t matter, but for larger teams, do you see the second in command being the manager, if you will, of the rest of the leadership team? Or does the entire leadership team report to the CEO or does it matter?

Cameron Herold (26:00):

Yeah, as a company gets to about a hundred employees, when you go from 30 to a hundred employees, the second in command, the COO at that point would probably be ACO title, usually has most of the organization reporting to them. The CEO might have a couple of functional areas that they’re very strong in, like legal or finance or it, but it really does become very much a divide and conquer where all of the C-level and all of the VPs report to the COO and the CEO. The CEO should only ever have a maximum of five direct reports because they also have culture, legal and strategy. And I call those direct reports even though most companies don’t have a legal department. So a head of let’s say a software company, they’re going to have those three business areas. In addition, I’d like to see the CEO really managing a maximum of two or three people so they can spend more time on strategy, more time on risk mitigation, more time on culture, more time around thinking about people.

Stephanie Everett (26:59):

Oh, yeah. Well, that’s super helpful and I think it’s helpful to just call out because I think it’s easy to read all these business books and say, oh, I need to be doing this. And I think what you’re reminding us is the complexity changes as the company matures and grows and changes. And I think that’s really a helpful framework to keep in mind that there’s no one kind of answer. It’s going to keep evolving.

Cameron Herold (27:24):

It’s also interesting that I was a great second in command for 1-800-GOT-JUNK. I would be a horrible second in command for 90% of our COO Alliance members because I don’t have the skills or competence to match their CEO’s weaknesses, or I’m not coming in with enough industry IP that I would be good in the role or that the industry or the company itself is at a different trajectory or a different season than my skillset matches me for just like the current COO at 1-800-GOT-JUNK who I’ve happened to known for 35 years. We started a fraternity together in Ottawa, Canada. I was president the first year he was president the second year. Now he’s COO got junk. He’s been an amazing COO to take them to 450 million, but admittedly, he would be useless in the first six years that I was there because he didn’t have the skillset to match that small entrepreneurial size company and scale it to the a hundred million mark. So even though you might be the perfect fit for the CEO, you also need to be the perfect fit for the season that the company is in as well.

Stephanie Everett (28:29):

Love it. Okay, last question. One of our values around here is stay curious. So sometimes I just like to ask people, what are you learning or what are you working on either personally or professionally that you might share with us?

Cameron Herold (28:43):

A couple things. One, my wife and I sold everything about two and a half years ago, and we’ve been traveling full-time ever since. So the ability to live and work globally, 41 countries in the last two years. Now being resident of Dubai, I’ve been paid to speak on every single continent including Antarctica. So the ability to spend time and collaborate and work with entrepreneurs and COOs from all over the world has allowed me to stay curious, but also just to be inundated with all of this incredible information and just seeing the business landscape from a very different perspective has been fun. And then secondly, I’ve really worked hard to invest in my own growth. I talk about investing in your leaders and putting your COO into the CO alliance or your ops people into the ops spot. I’m a member of a bunch of different mastermind communities where I go to different mastermind events every year and connect with other CEOs where I can actually just be in the room and not be the smart person in the room.

(29:40):

I can be an attendee like everybody else where I’m there absorbing and learning. And I think that there’s something to be said for that. Stephen Covey talks about sharpening the saw. And I think if you give yourself time to truly sharpen the saw, that allows you to be curious because you show up as the dumb person in the room, and then I call it ideas having sex. I learned something from Stephanie and something from Fred and something from Bill. And those three things that I’ve learned have an idea baby, and those become the ideas that I need for my company. So that’s one reason. And then I get super inspired as well. When I’m traveling or when I’m connecting with other businesses, it also fuels me up and I come back into my business as that chief energizing officer where I come back in with ideas and optimism and energy that fuels the organization as well.

Stephanie Everett (30:29):

Awesome. I love all that. I love that idea. Sex, I’m going to remember that. We won’t forget that one because you’re so right. Thank you so much for taking some time out of your travels to talk with us. We are going to make sure the show notes have all the links to your book and to some of the other resources that you shared with us, and I’m just really grateful to have this time with you.

Cameron Herold (30:51):

Thanks, Stephanie. I really appreciate it. Please send over the links when this goes live so I can share this with our audience as well. But really appreciate the time today.

Announcer:

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