The 8 Pillars Of Being A Second In Command (aka the COO) With Cameron Herold

Sean Lane: Hey, everyone. Welcome to Operations, the show where we look under the hood of companies and hypergrowth. My name is Sean Lane. When I first started this show, I asked around to different folks in my network for other podcasts that they listen to about operations and the work of people in operations. And to be honest, at the time, there wasn't a lot out there, which is one of the reasons why we started this show in the first place. But there was only one podcast that I kept hearing about from multiple people and multiple people telling me that I needed to check it out. That podcast is called Second in Command, and it focuses on exclusively interviewing chief operating officers who are, you guessed it, typically the second in command to the CEO. The host of that podcast and our guest today is Cameron Herold. In addition to his podcast duties, Cameron is the founder of the COO Alliance, the former COO of 1- 800- GOT- JUNK. He's a keynote speaker and author and, honestly, one of the foremost thinkers and leaders on the work of COOs and their relationship with CEOs. In short, he's a pretty big deal. And so I'm really excited that we were able to get him to spend some time with us on our show. In our conversation, Cameron and I talk about the eight core areas that a COO should be measured on. We cover how operations teams can help to execute a company's vivid vision and why his stand up meetings were religiously scheduled from 10:55 to 11: 02. To start, with all the different data points that Cameron has amassed over the course of his career, I wanted to ask him if he has been able to come up with a single way of defining the role of the COO or is it really that different between different companies.

Cameron Herold: It's truly that different. In fact, Harvard did an article about 15 years ago called The Misunderstood Role of the COO, and they identified seven distinct types of chief operating officers, from the MVP to the error parent to the partner to the change agent. I forget exactly what all seven of those were, but they really showed that the second in command to the CEO just plays a very, very different role. And probably not unlike marketing has changed over the years, right, where you used to be a very offline or product- based, and now you have to have a blend of maybe online or offline and you're certainly taking into account much more digital, the difference with the COO is they also have to be the yin and yang balance to the CEO. So the second in command is really usually in charge of all the stuff that the CEO sucks at. So it's just hard to actually say at times what the role is other than if the CEO is sick for six months, the COO typically would be the one running the company. Then you can get into title differences, right? Because really, you get the scope and the responsibility, but people tend to give away titles a little too quickly. So the COO could be the general manager or the VP of operations or director of operations or the COO. Just like the head of finance might be a controller or a director of finance or a VP of finance or a CFO, the second in command is really probably what we're talking about more than the CEO.

Sean Lane: And that was going to be my question, which based off of those different titles that might have gotten mushed together there, is there a moment in a company's evolution where you have found to be the right time for the introduction of that true second in command?

Cameron Herold: Yeah. The first step is that, if you don't have an executive assistant, you are one. So often, what happens in these growth companies is people are working harder, working faster, working harder, working faster. And they're like," Oh, I need a second command." No, you just need a bunch of the administrivia off your plate. And if you could actually delegate all the stuff that you're incompetent or competent at and get somebody to handle that for you, or if you can get stuff that's really way below your pay grade and having an executive assistant take stuff off, it usually frees you up from needing a true second in command for maybe six to 12 more months, which is really powerful and often a great money saver when you can do that. So the true second in command comes along where the CEO finds that they're really working on big impact stuff, stuff that is at their pay grade or above as well, and they just don't have the time to do it all. And a lot of the stuff they're doing drains them of energy, whereas if they were able to bring on a true partner, a really yin and yang who could handle all the stuff that they hate, handle all this stuff that they're not that great at to free up the time of the CEO to be able to work in their unique ability, right? You delegate everything except genius. That's really when the real leverage comes in.

Sean Lane: And so as you've looked at how these relationships have evolved, one of the things that I think is super interesting is just the sheer number of data points that you've been able to collect, right? Whether it's through your work with COO Alliance or you're up to over 130 episodes on the Second in Command podcast, when you look across all of those data points, are there any universal truths or big glaring similarities that you're able to extract from all those different COOs?

Cameron Herold: Oh, for sure. And we actually created a scorecard that allows COOs to rate themselves against other COOs, or it allows the CEO to rate their COO. And we crosstalk.

Sean Lane: Oh, interesting.

Cameron Herold: Yeah. And we actually came up with eight core areas that the COO rates themselves against, and those eight areas just really give a real good glimpse at either their skill set on specific areas or maybe areas that they should be working on, areas they might be able to be getting better at.

Sean Lane: Interesting. Do you mind telling us about one of those core areas that you find to be helpful to score those COOs on?

Cameron Herold: Yeah. I'll walk you through all eight of them really quickly. The first one is the vision being aligned with the CEO, right? Are they truly on the same page with the vision of the CEO? The second is do they have a strategic plan in place to make that vision come true and has the CEO signed off on their plan? The third would be that they have the people systems in place for recruiting, interviewing, hiring, onboarding, and training of people. The fourth is do they have the right meeting rhythms and the systems in place for meetings across the organization? The fifth is do they have the financial systems in place to make sure that they can scale the company in the most efficient way? The sixth is do they have the basic job skills to do the job of the COO? The seventh is do they have a tribe of mentors that they can actually turn to and reach out to, and do they actively work with those mentors? And then eighth is do they have the systems in place for culture to turn their company into a magnet for great people? Those tend to be the real good benchmarks for a great second in command.

Sean Lane: You can see why I needed to have Cameron on the show, right? He not only has this unique perspective on being the second in command, but he also has a tactical list of things you should be measuring yourself on if you want to be one. In case you missed all of those, Cameron's eight core areas of being a second in command are, one, an aligned vision with the CEO, two, a strategic plan, three, people systems, four, meeting rhythms, five, financial systems, six, the job skills to do the job, seven, a tribe of mentors, and, eight, a culture that is a magnet for great people. And let's be honest. I wanted to go deep with Cameron on all eight of these different areas, but the one that jumped out to me immediately as something that's relevant to this show was number seven, having a tribe of mentors. I often find myself looking for mentors or role models at companies that are similar to Drift. Maybe it's a similar business model, or maybe there are a couple of years ahead of Drift in terms of their maturity. But what I like about Cameron's show is that he has COOs on the podcast from a wide range of industries and business models. So I asked him which type of mentors should I be seeking out for my tribe.

Cameron Herold: So, first and foremost, you're looking for a second in command or a COO who really is great at the stuff that you're not great at and loves doing the stuff that you don't love doing. So that really is the first area that you're starting, and then secondly, that they must have a really strong trust with you, that you really have to be able to almost turn your keys over to them, give them the passwords to the business day one and have done all the interviewing and reference checks that you really understand them before they start. That's where you'll get the most leverage. Whether or not they have industry experience depends. I think if you're in a fairly technical kind of business, yes, then it can really help that they have some technical expertise. But if you're in a business- to- consumer type space or a business- to- business space, often they just need to learn the product or service. And we sometimes think that that's more important than it really is. When I was the second in command for 1- 800- GOT- JUNK, I came into the business and after spending two hours or three hours out hauling junk, I turned to the CEO and I said," Okay. I know the business." And he started laughing. He goes," I've been doing this for 10 years. There's no way you know it." And I said," Well, we're not about junk removal. It has nothing to do with picking stuff up, putting it in the truck, and getting rid of it. We're actually in the customer service space and we're in a culture space where we need to turn our company into a magnet for people." So when I started laying out the plans for him, he looked at me and went," Holy shit. You actually know the business now better than I do." So it really didn't matter. But if I was in a more technical... Let's say I was in the telephone space, right? I used to coach the CEO and the second in command at Sprint. You don't really want a second in command at Sprint who doesn't understand the telephone industry, right? It would take a lot longer for that person to come up to speed. So you'd probably want someone out of telco. So I guess it just depends on whether you're in a very technical space as to whether the technical expertise trumps the business expertise.

Sean Lane: I also found the first two core areas that Cameron mentioned to be a really interesting pair, one, an aligned vision with the CEO and, two, a strategic plan to implement that vision. Before chatting with Cameron, I read one of his books called Vivid Vision. The book itself is a playbook for CEOs to lay out a three- year vision for their companies in a very specific way. And Cameron makes a big deal in the book that the CEO needs to be the one who develops and articulates this vivid vision. So based on what he was telling me about this ying and yang relationship between a CEO and a COO, does that mean that the CEO then hands off their vivid vision to the COO to turn that into a reality?

Cameron Herold: Exactly right. It's very similar to a homeowner who wants to build their dream home. In this case, the homeowner is the CEO of the project, and they're going to give all of their vision, ideas of what they want the home to look like, maybe photos and drawings. And they'll give all that to the contractor, and they'll sit and talk to the contractor about their family and how they entertain and how they live and showing them pictures and examples so the contractor understands the vision for this dream home. The contractor then goes away and comes back with blueprints or plans to make their vision come true. The homeowner signs off on the plans and the contractor signs off on the vision. So those two things are now locked and loaded and you hand the vision and the plans to the employees, and the workers can literally build the house without ever talking to the homeowner. In the business world, it's exactly the same. The CEO's role is to articulate in a four or five page description of what the company looks like, acts like, and feels like three years in the future so that the leadership team, led by the second in command, the COO, can put the plans in place to make that vision come true. And what usually happens is you're always trying to herd cats and you're trying to organize people and hold them accountable and manage them. Well, it's mostly because nobody has any idea what we're really trying to build, nor do they even understand how their projects or tasks fit into a bigger picture. But when they have that clear vivid vision that the COO can sign off on, the CEO no longer needs to get involved in the day- to- day or the how it's getting done, because they know the team is really clear on what they're building.

Sean Lane: That's super interesting. And one of the things that my mind goes to, and I think this is probably a default ops thing, is I immediately zoned in on the part of the book where you're talking about basically reverse engineering from the vision and then figuring out how to operationalize it from there. Can you help people understand, if we are the ones within our companies who are receiving this vision from our CEOs or from our leaders, where do you even begin, right? How do you start that reverse engineering process and start to break that three- year vision down into more bite sized chunks?

Cameron Herold: It's interesting. With the COO Alliance, we spend a lot of time with our members of the COO Alliance talking about reverse engineering, project planning, goal setting, strategic thinking, basically figuring out how to put the plans in place. And then I've got a podcast called the Second in Command podcast. And it's amazing listening to all these CEOs, because we never interview the CEO. We always want the rest of the story. And it's really interesting to hear them talk about how they put the plans in place to make it come true. So I want you to think about building a home for a second again, that you have the foundation that you pour first, right? That concrete foundation is the base of the home. And if the foundation is weak, it's really hard to put up the walls and put in the electrical and the plumbing. So you need to do a strong foundation. Then you put up the walls, then you put in the electrical and the plumbing, and then you put in the dry wall. And sure, the homeowner's super excited about the Wolf stove and the beautiful cabinets, but that comes in at the very end or towards the end. In your vivid vision, there's parts of your vivid vision that are the core foundational parts of your vivid vision. And I almost talk about it like a jigsaw puzzle, where the four corners of the jigsaw puzzle are your vivid vision, your BHAG, your big, hairy, audacious goal, the core values, and your core purpose. So it's making sure that you have systems in place to understand those four things, to live those four things, to communicate those four things, to align people around those four areas. Those are the foundational building blocks. And then the first wall or the first side of the jigsaw puzzle are all of the people's systems. So this is where the COO is putting in place all the systems related to recruiting, interviewing, hiring, training, onboarding, and the leadership development of people and also getting rid of the wrong people, right? All of those systems related to people are very foundational. And then from there, it's all the strategic thinking systems. So it's the strategy, it's the planning, it's the annual planning, it's the quarterly planning sessions, it's the goal setting. And then it's your meeting rhythms, would be the third side of the jigsaw puzzle, would be all your meeting rhythms, so putting plans in place for how to operate meetings. That's why I wrote the book Meetings Suck, was for every employee at every company to actually understand not only how to run meetings, but also how to participate in them and manage up in them and contribute in them or how to opt out of the meetings so that they can actually work on their higher priority work. And then the fourth side of the jigsaw puzzle are the financial systems. And then in the center of the puzzle is all the culture systems. So we really want the second in commands to think of the businesses that way and build it very foundationally. And that's why the strong, fast companies really can scale, is because their base is so strong. We built the number two company in all of Canada to work for, but our vision was really strong. Our core values, we obsessed over them. Our BHAG was clear. Our core purpose was clear. All the people systems were clear. It was easy to scale it when you have all those pieces in place.

Sean Lane: It's so funny. As you were starting to describe the house metaphor, I was immediately calling back to the eight core scorecard areas of a COO. And it was amazing how then, as you were describing the different parts of the house, literally they're the same things, right? It's the same core competencies. It's the same skill sets. And your being able to repurpose those in the execution of the vivid vision brings it full circle back to the skillset you said a second in command needs, right?

Cameron Herold: Well, and it's interesting. If you think about people in relationships, I had the second in command for Rippling on my Second in Command podcast, Matt. And Matt was talking about he has a document that he gives to every new employee, and it's the operating manual for Matt. It's the COO's operating. It's how he ticks. It's what drives him crazy, what pisses him off, what turns him on, how he manages projects, how to communicate with him, how to show up at his door. He gives a two- page document, which fast- forwards everybody's relationship with him. This is a guy who's thinking about core values and people and onboarding of people in a really specific way.

Sean Lane: I don't care if you're a COO or you're someone more junior building a team inside of hypergrowth. The four foundational corners of the puzzle that Cameron describes here can be a blueprint for all of us. It's not easy. He talks about the foundations, the walls, the pieces in the middle. It's not meant to be easy, but it can become more clear. The path to building a successful team and to being a successful second in command is all within those different puzzle pieces. But let's be honest with each other. For every grand vision or lofty goal you've ever heard, you've also seen plenty of ideas that never make it past that initial PowerPoint deck, right? Cameron's book talks about not just creating the vivid vision, but executing and, more importantly, maintaining it. My question was how we actually do that maintain part. Things change so quickly around me every single day. Is a three- year plan realistic?

Cameron Herold: Yeah. The first one is to make sure that you only put in place a one- year plan, because by the time you get into a three- year plan, everything's changed. So you have a three- year vision, right? The vivid vision is a three- year document, but the one- year plan that you'll execute on. I also have four core goals that I really organize the organization around. The first one is your employee net promoter score, because the happier your employees are, everything goes better. The second one is your customer net promoter score. So you'll notice I'm not talking about revenue or profit yet. It's how happy are my employees, how happy are my customers. When you obsess about those two things, your profit takes care of itself, as does pretty much your revenue. So those are the four goals I go after: employee net promoter score, customer net promoter score, your profit as a pure dollar figure that we're chasing down annually, and then a revenue goal. I also really like to stretch into my goals. So I don't forecast where I'm going to be for the next year. I decide what I want my revenue to be three years out. I decide what it needs to then be two years out. And then I decide what my revenue needs to be in 12 months. And then I figure out a plan on how to make that happen within our core values and within our core purpose. So then we figure out how to make those things happen. If we were thinking at 1- 800- GOT- JUNK, we had six consecutive years of 100% revenue growth. Six years in a row, we grew at 100%. So we went from two million to 106 million in six years with no debt, we gave up no equity, and we ranked as the number two company in Canada to work for. But we figured out how to make those growth numbers happen. And that's what allowed us to say no to a lot of stuff, but to say yes to the right stuff.

Sean Lane: Over the course of those six years, and certainly in the work you do today too, I'm curious how you either thought about it yourself when you were in the role or how you coach operators today to flex that longer term thinking muscle, right? Because I know for me personally, you end up so in the weeds, you have to really make an effort to abstract yourself and think longer term. I know that the vivid vision is meant to be a CEO's exercise, but I'm curious how you coach COOs and second in command and ops folks to build that longer term thinking muscle. Or do you think that they need it?

Cameron Herold: No, they absolutely need it, especially in a growth company. So we'll talk about first hypergrowth, so this 100% or greater. You need to have a monthly meeting for at least two to three hours where your leadership team talks about stuff six to 12 months out on the calendar, just brainstorming, blue sky, throwing shit against the wall, Post- it notes, what if- ing. And you what if the good stuff that could be happening, you what if the bad stuff that could be happening. So you're thinking about opportunities and what could be coming down that road. So we, every month, would have a three- hour meeting. We had an ongoing list of topics that we'd want to brainstorm on. I'd be like," What would it be like if we opened up in Australia?," or," What would it be like if we did acquisitions?," or" What could it be like if we went public?" And we'd just brainstorm around stuff, typically 30 minutes to an hour. But we were doing that every single month. It was in our calendar for three hours a month. If you're growing at 25 to 100% growth, you probably only need to be doing that on a quarterly basis. And if you're growing anywhere between seven and 15% growth, maybe you need to have strategic time as part of your normal quarterly or annual planning meetings. So that was our strategy meetings, and that was in addition to the two day annual planning meeting, which was about strategy, vision, goal setting, and the plan. And then we also had a quarterly half day to a full day meeting to press reset on the plan and again talk strategically. So but we had a lot of time baked in our calendar for strategy.

Sean Lane: Yeah. And I can see how that ties back into the meeting rhythms. Do you view it as ops' role to drive those cadences or drive those meetings and bring people together for that what if exercise?

Cameron Herold: Yeah. It's operations' role to think about strategy and figuring out how to get there. And then IT and finance and marketing and everyone else can figure out how to make that come true. Yeah. I find it's dangerous at times to have IT driving strategy, because they often go in a direction where the tail can start to wag the dog.

Sean Lane: The question they would ask then is," How would we do this thing we want to do?," instead of," What are the things we want to do?"

Cameron Herold: Or they want to build stuff and integrate stuff [ inaudible 00:22: 34 ] necessarily drive strategically, whereas operations tends to have a more holistic view of the customer and the employees and the market and the economy and our cashflow and resources, whereas IT can tend to be fairly singular around its approach.

Sean Lane: And if you're doing that, let's say you're in that hypergrowth category you mentioned and you're doing this on a monthly basis, certainly the circumstances can change that quickly. Is it hard then to maintain some level of consistency in the course? How do you know if the thing that you've thrown out there as the what if, you've given it enough time for it to work or that thing is still not fully baked and it needs another month before you abandon it?

Cameron Herold: Well, you've got your weekly leadership team meetings where you're typically meeting for 90 minutes to talk about the core projects that you're working on to make the quarterly goals happen, right? You're debriefing with each other and committing to what your goals are for the next week and talking about obstacles and helping to remove obstacles together. And then we also used a daily huddle, where we had an all company standup meeting for seven minutes a day. It was held at 10:55 until 11: 02, where we shared news, we went through the key numbers, we did our project updates, and then we talked about missing systems and frustrations. So you have that daily pulse. Those rhythms in your calendar are what help scale a company.

Sean Lane: That's amazing. And we talk a lot about systems and routines and cadences with folks on this show. And I love how you still remember exactly the start and stop time of those meetings and how critical those were to your operating rhythms.

Cameron Herold: Yeah. I've got companies all over the world using those systems now. But we started our daily huddle based on a concept we learned from Verne Harnish with Rockefeller Habits, put it in place in 2001 where we had about 20 employees. And fast forward 19 years later, 1- 800- GOT- JUNK is still doing daily huddle and they've never missed a day in 19 years. The reason it was 10:55 was the first part of the day where the energy level drops is 11: 00 AM. The second part of the day when energy level drops is 2: 00 PM. So the good times to run huddle are usually first that 11: 00 or 2: 00. We chose 11 as a good spot to get a burst of energy before lunch. And then the reason we do it for seven minutes is, if it's much longer than that, it drags. So we picked a very defined time, and then we had everyone's computers set up with an alert. So at 10: 53, their computers would ring. They'd stop whatever they were doing. They'd finish phone calls, finish meetings. They'd walked to the huddle area, and we'd start exactly on time and finish exactly on time.

Sean Lane: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. All right. Best book you've read in the last six months.

Cameron Herold: Hard Thing About Hard Things by Ben Horowitz. It's just very tactical, strong, bite sized stuff that you can implement right away and it's really, really tested.

Sean Lane: I love it. Favorite part about working in ops.

Cameron Herold: The people. I really, really like growing people. I love helping to grow their confidence and grow their skillset and remove obstacles and aligning them. I love the people side of it.

Sean Lane: All right. Flip side, least favorite part about working in ops.

Cameron Herold: The people. They can be stressful. They can be... It can get in the way of me getting my work done. It can be hard. It can be challenging. Again, the conflict... But so I try to teach them. But yeah, the people can be tough.

Sean Lane: So I know you run the show, but someone who impacted you getting to the job you have today.

Cameron Herold: Someone that impacted me at getting to the job? Joe Polish, who started The Genius Network. I've been a member of The Genius Network for about six years. He and I were daily accountability partners for two years. And at one of his Genius Network events, I just had this blinding flash of the obvious, that there were dozens and dozens of organizations for CEOs, right? You've got YPO and Vistage and EO and Genius Network and Baby Bathwater and Maverick and Mastermind Talks, et cetera, et cetera. And there were groups for engineers and lawyers and marketers, but there was no group for the second in command. And so I just decided to model the COO Alliance around a lot of what The Genius Network was doing. And it just took off.

Sean Lane: Can you tell me more? What's a daily accountability partner?

Cameron Herold: So we used an app called CommitTo3 that a friend of mine actually developed based on a speaking event that I was hired to do. He saw me at a speaking event talking about setting your daily priorities. And if you just pick the daily top three or top five things that you need to get done, if you just did three highly impactful things a day times the 250 business days that we have in a year, you'd actually get 750 impactful things done, instead of getting stuck in your email or working on busy work. So there's an app called CommitTo3. It cost three bucks a year. And you commit your daily top three goals to your accountability partner. They commit theirs to you. The first person to set their goals, it pings the other person as like," Oh, shit. Joe has already set his daily goals for the day. I should do mine." And then at the end of the day, you click them off as getting them done. And it's just about the accountability of working on highly impactful things.

Sean Lane: I love that. I'm definitely going to have to download that. All right. My last question is usually one piece of advice for people who want to have your job someday. But I'm going to switch it up in honor of having you as a guest and I'm going to ask you the question that you ask all of your guests, which is, if you were to go back to your 22 year- old self, what advice would you give yourself back then that you know to be true today?

Cameron Herold: I actually wrote it in chapter 17 of my very first book Double Double. I wrote letters to my younger self. And I think I documented 65 lessons that I knew to now be true that I wish I'd known when I was younger. But I guess the core one would be to just not take myself so F- ing seriously. None of this actually matters. This doesn't... Nothing matters. We're all going to die. Why don't we just have more fun and laugh a little and enjoy our work along the way? Because none of us are getting out of this alive. We're just all walking each other home.

Sean Lane: I noticed that came up a bunch in your vivid visions as well. You were always saying that the future version of yourself was very at ease. People were saying how comfortable you were in the work you were doing and how well suited you were for what it was you're doing. So I can see how that worked its way back into the visions you were given to yourself as well.

Cameron Herold: It's just more fun to do it that way, so just little tiny things that you can do to have more fun along the way, and then it just... That bleeds into your engagement with your customers and your employees. And it bleeds into people having more fun, which means they're going to get more productivity. And the other reality is you don't stress out as much, because we're not going to get all this stuff done. We're never going to complete our to- do list. If we do, we're just going to add more goals. So you may as well enjoy the path.

Sean Lane: Thank you so much to Cameron for coming in and joining us on this week's episode of Operations. If you want to learn more about Cameron, you can check out all of his work, his podcast, his books at CameronHerold. com. That's C- A- M- E- R- O- N, H- E- R- O- L- D. com. All right. If you like what you heard on this week's episode, make sure you are subscribed to our show so you get a new episode in your feed every other Friday. And if you're really liking what you're getting out of this show, make sure you leave us a six- star review on Apple podcasts or wherever you get your podcasts. Six star reviews only. All right. Thanks so much for listening. That's going to do it for me. We'll see you next time.