Ep. 101 – Special Q&A with COO Alliance Founder, Cameron Herold

In this special episode, COO Alliance founder, Cameron Herold answers some burning questions from his audience about growing your business, setting the right internal systems in place, and improving your relationship with your CEO. What are the signs that a company needs a COO? How do you value and identify adaptability in teams? What are the most crucial roles that need to be fulfilled when starting a business? Where should you put your focus on when growing your business? Get the answers to these questions and more on this episode.


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I thought what I would do is a bit of an ask me anything. I went out on Facebook and LinkedIn and asked one question. If you wanted to ask me a question about leadership or being second in command, what would you ask me? I’m going to go ahead and give a Q and A and I’ll try to give everyone’s name on these. The first question we have is from Ian Wyatt, the President and publisher of Wyatt Investment Research. He said, “Many smaller businesses below $10 million in revenues get along without a COO.

What are the signs that a company needs a COO? If you were consulting with an entrepreneur, how would you know when to recommend that they get their first hire?” It’s a great question. First off, what I’ve always said is, “If you don’t have an assistant, you are one.” That’s a quote that I learned from a friend of mine, Jack Daly. I’ve often said that. The first thing I would do is go out and hire an executive assistant. Secondly, look to hire a second in command.

Also, be careful with the title you put in place for a second in command. It could be a director of operations, a general manager, a VP of operations or a COO. Be careful with the title getting too big. The title should match the roles and responsibilities and the compensation that you want to pay. Once you have an executive assistant and you’ve offloaded all the administrative off of your role, and you’re still left working on a lot of big projects that are high impact projects that require a bunch of expertise and are draining you, and preventing you from spending a ton of time in your unique ability. That’s when you want to hire that second in command. It typically comes in the 30 to 50 employee range. For sure when you hit 100 employee range, by that point, you have more opportunities. It’s not so much of a need to, it’s when you can, it’s an opportunity that you can go to.

The next question we have is from Ross Thornley, who’s an entrepreneur at Adaptability Quotient out of the UK. Ross and I met at an event that we both go to called the Abundance 360. Ross’s question is, “How would you value and identify adaptability in teams? How might you advise people to recognize what to stop doing and what to do more of in an exponential world, when to let go and when to lean in?” Ross is building a personality profiling model that he’ll be bringing online. I would look to some personality profiles for my teams and start building what we call a unique ability team. I’m getting people to work on the areas that they’re strong in, and getting rid of the areas that they suck at or drain them of energy. Often in the school system, we were told to work on our weaknesses.

What I love to do is delegate everything except genius and have people work on those areas that they’re strong in and that give them more energy. The more that they work in that, they’re going to get better at it. They will spend more time learning about it. Their energy will spin-off into the organization as well. What I try to do is adapt in terms of getting rid of the projects and initiatives that drain somebody, and putting those onto the plates of somebody else that loves them. An example for that is I’m pretty bad at written communication. I’m much better thinking out loud doing speaking events or coaching. I find that when I write things, I’m often fairly acerbic. I come off too abrupt so I write everything in bullet points. I’m a bad writer when it comes to sending out longer forms of messaging. What I’ll often do is take my rough points and give them to a writer who can polish them and make them pop-off the page. They love taking the work and writing it. They’re great at writing. It gives them energy. Whereas for me, writing drains me. That’s what I try to do in adaptability. It’s getting people to work on their unique abilities.

The next question we have is from Anthony Perry, who’s the VP at National Media Sales, “How do you create a culture where it’s okay to admit feeling like you have impostor syndrome?” It’s okay to say that you have impostor syndrome. A lot of us are so worried about being judged but the reality is every day, every one of us wakes up thinking this is the biggest thing we’ve ever done. We had one of our COO Alliance events. We have the only network of its kind in the world for second in commands. One of our COO Alliance members, that was his first event, pulled me aside privately and said that he’d been up all night. He had a sleepless night and he skipped our group morning yoga that morning because he wanted to hang out with his kids and get a hug from them. I said, “What’s wrong?” He said, “I feel like a bit of an impostor. I feel like I’m not the right fit in this role.” I was like, “I think the exact opposite. I think you’re amazing in the role. Let me ask the group for a second.”

We went and asked the entire group, first about him and secondly about themselves. All 30 of our COO Alliance members that were in the room put up their hands saying that they feel like an impostor as well. It’s recognizing that everybody feels like they’re making it up as they go. How are we all supposed to have the right answers? The school system has conditioned us to feel like we’re supposed to be experts when we’re not. Vulnerability is saying, “I’m great in these specific areas, but I need help in others and realizing that everybody is struggling at times too.”

Kevin Clancy from Ono Media says, “What are the benefits of having a multigenerational workforce?” First off, you have to. You think about you’ve got Gen Z. They’re the 4 to 22-year-olds. You’ve got the 20 to 22-year-olds that are coming into the workforce now. Maybe in summer roles, interns, apprentice or early-stage roles. You’ve got all of Gen Y and the oldest Gen X is only 54. Baby Boomers are 54 to 75. You’ve got pretty much four generations in the workforce working for you. It’s not so much what are the benefits of it, but how do you leverage each of the strengths that each of those groups bring to you. Baby Boomers bring a bit of wisdom. They’ve been in the workforce for a long time.

I was speaking to somebody as we’re going through a bit of a financial crisis in the Coronavirus stuff. Somebody is completely freaking out about the stock market going down. I’m like, “I guess you were too young to remember 2009.” He goes, “I was too young to remember 2009.” I said, “You don’t even know about 2001. You don’t know about 1997.” He’s like, “No, not at all.” Someone like me who’s 54 brings three different stages of financial collapse experience into my day-to-day wisdom, strategic thinking and planning. As an example, I’ve been planning for this downturn and got excited when I saw the collapse because I was able to start deploying a bunch of cash. Cash is king in a recessionary market. For anybody who’s young, early Gen Y, they think it was always going to be great. It’s recognizing that each group brings different strengths. Each group brings different weaknesses, identifying what those strengths are, and helping the other groups in that unique ability team idea.

SIC 101 | Second In Command Q&A

Second In Command Q&A: Culture trumps strategy.


The younger stage of Gen Y bring a lot of the apps and technology tools, but they don’t necessarily know how to grow a company or why they’re doing what they’re doing. Gen X and the older Gen Y might have a bit more of the wisdom, a bit more tech-savvy. You have the Baby Boomers that have a lot more of the wisdom. They were able to build teams and teams of teams. They understood how to get stuff done in a slower environment, but how to be more methodical and get the right things done versus the spray and pray that we’re often doing now because we’re moving so quickly. It’s identifying some of those unique ability areas and trying to leverage those.

The next question is from Chris Daigle. He helps business owners scale profits. He said, “How does the COO step into the limelight? It seems like outside of their home organization, they’re unsung heroes, which is a huge missed opportunity to establish authority in the marketplace.” That’s one of the reasons I started the COO Alliance and also started the Second in Command Podcast. With the Second in Command Podcast, I wanted the rest of the story. When I was the COO for 1-800-GOT-JUNK?, I was very forward-facing. I was outward-facing with the media doing speaking events. It was Harley Finkelstein from Shopify. There are many COOs that play the outward-facing role because the CEO likes to play the inward-facing role. There are also many COOs who recognize the opportunity to go outward-facing. It’s putting your hand up and saying that you want to do more of those outward-facing, forward-facing roles and jumping into that. One definite way is to read the book Free PR, and start generating some press about yourself and the company. That will help give you a bit of a platform both within your company and outside the business as well.

Rob Bernstein who is in leadership development said, “To what extent do you consider the culture of an organization as opposed to the numbers prior to any M&A activity? If so, how?” I always consider the culture of the organization. I only consider the culture of the organization first. Culture trumps strategy. If you’ve got a high employee Net Promoter Score, it generally means you’ve got an engaged workforce. You probably have high revenue per employee, high profit per employee, or at least the opportunity to get that. You’ve got engaged people that are excited about growth and culture, probably low turnover. That tends to translate into happy customers. I look for companies that have that.

If we’re doing M&A opportunity where we’re acquiring companies that maybe don’t have a strong culture, what I’m looking for are the right culture-fit people to keep, and then which ones can I get rid of that are the wrong culture fit so that we can do a quick turnaround. The biggest opportunities are to turn around companies that have a bad culture, then to do acquisitions to look for companies to bring under the fold that maybe have great cultures. Focusing on employee Net Promoter Score and employee engagement and culture is what’s going to drive your revenue and profit numbers in the organization for sure.

The next question is from Sarah Stanley who’s an employer, brand and culture leader. She said, “Where does empathy in connection with your employees fit into decision-making and that of the leadership team? Does everyone have it? If not, how do you thread it into decision-making if it’s not everyone’s skillset?” One of the things that we did back at 1-800-GOT-JUNK? that was key was we hired a head of people. For us, the head of people considered the people impact of every decision and every plan that we were putting in place in the organization. When we started to think about the people impact of our growth, our strategy, our marketing tactics, what we were saying to customers, etc., thinking about that at the leadership team level gave us some additional insights and reasons to either green-light or red-light certain projects. We also built a habit of doing a lot of skip level meetings where the CEO would skip over his or her direct reports and meet with their next team. I would go and meet over top of my VPs and meet with their next team, etc. Skip level meetings were a great way to be empathetic and to be engaged with the employees.

We also got rid of all of our offices completely. I’ve coached all of my clients to get rid of offices completely, believing that if you have a complete open office environment, you’re sitting with your team. You’re sitting with your people. You are listening to what they’re saying and what’s going on. You’re observing them. What I would do is sit at somebody’s desk with my laptop for a few days in IT. I would switch and sit in PR for a couple of days. I’d switched and sit in marketing. By sitting in different parts of the business, you get to see what’s happening, be empathetic and engaged with the employees.

Let’s go to the next question from Joe Showcraft. Joe asked a word association game, the first word that comes to mind with these words. He said, “With leadership.” With leadership, it is mentoring. For me, it’s all about growing people. For “loyalty” is Net Promoter Score. The higher the Net Promoter Score, the higher the loyalty is going to be. For “empathy,” it’s my kids. I’m thinking about my team like they were my kids, not in a subservient way. I care about them and I have their feelings at heart. “John Candy,” the first word that comes to mind with John Candy is Jack Daly because he changed his name on Facebook to be John Daly. I think Jack Daly and John Candy remind me of each other for some funny reason. “Marketing” is a guy out of Columbus, Ohio who used to say, “Early to bed, early to rise. Work like hell and advertise.” “Accountability” is hiring the right people. It’s hiring accountable people. Somebody said they wanted to hire someone who would hold his people accountable. I said, “No, hire accountable people. It’s easier.”

The next question we have is from Laurie March, “Is it ever right to do a scorched earth and restart your culture if it’s wrong? If so, how do you support those who remain after a mass firing? What’s one blind spot that founders usually have when it comes to culture?” If you’ve got a bad culture, you always are firing those cultural cancers. I think of them like cancerous tumors in our body. If you know you’ve got the wrong people, you get rid of them right away. If you identify a whole bunch of them, you get rid of them right away. I always do cut deep, cut ones. If I’m firing one person, I look across the organization to see if there are others. I get rid of them all on the same day. I’m always looking to fire the wrong culture-fit people and people that aren’t getting the results second.

SIC 101 | Second In Command Q&A

Second In Command Q&A: What the CEO is starving for is truth, and when the COO always tells them the truth, they respect that.


The way that you support those who remain after a mass firing, we had to fire 150 people for a company that I was running back in Seattle. We had what we called survivor guilt and we stayed close to the conversation. We got out of our private offices and sat with them. We went for lunch with them. We went for coffees with them. We asked them how they were feeling. We identified that over the course of a couple of days and a couple of weeks, that started to change. At least after 2 to 4 weeks, they were back to normal. Maybe they remembered some of their old friends, but they had gotten through it. Remembering that it’s like a death, we’re all going to die. Everybody knows people who have been fired. People will get over it. It’s not obsessing about it for too long.

Paul O’Mahony said, “What size of company in terms of employees or revenue does a leader need to get the integrator in?” You want to get the executive assistant in first. After the executive assistant, you want to get the integrator or a second in command and be careful with job titles. You can be getting a second in command in the 20 to 30 employee range when you’re going to be getting your first key second. If you’re already building a management team as early as 10, 20 employees, you’re starting to hire some managers, those effectively are second in commands in a way. When you get into the 50-plus employee range, when you’ve already got a management team and you then have someone managing the management team, that’s probably when you’re bringing in the true integrator.

Clinton Senkow said, “When starting a business, what are the three most crucial roles or positions that you feel need to be filled in order to present the greatest chance of success for the business?” The first one is in the early stages you hire a jack of all trades, master of none. You’re hiring people that can do projects, can get shit done, can be entrepreneurial, can grow, can see and can problem solve. You’re looking for people who can also manage complex projects and manage outsourced people. In the earlier stage, it’s about people who can manage freelancers, people who can manage projects, and people who are good at leveraging technology and managing themselves. It’s less of the titles and more of the types of people you’re hiring.

Paul Fauss said, “What do you do when you believe the first in command is making the wrong decision?” That’s easy. You tell them they’re making the wrong decision. When you believe the CEO is doing the wrong thing, you tell them. I want everybody in the organization to be able to say and feel that they can point things out. What the CEO is starving for is truth, and when the COO always tells them the truth, they respect that. The key though is to not do that in public. Try to do it privately behind the scenes a bit because if you tell the CEO in public, in front of the rest of the team that they’re doing something wrong, they will often get a feeling that they’re back in the corner and they’ll come at you. If you do it privately, they’re often quite respective and receptive of that as well.

Ben Weir from Vancouver, he and I both met at Abundance 360 as well. He said, “What are your key principles on scaling a low six-figure company?” For me, it’s work like hell and advertise. It’s focusing on the critical few things versus the important many. It’s sitting and working on things that you can launch and get into orbit, so they’ll always be working. It’s about optimizing and automating things. It’s working on those critical few things versus being busy. I think so often entrepreneurs are busy and they’re distracted. The other thing is getting a clear vivid vision in place. I covered my concept of vivid vision in my book, Double Double, my second book, Vivid Vision and I also covered it in The Miracle Morning for Entrepreneurs. That’s a great tool to align people as well in the early stages of growing a company.

Jayson Gaignard said, “How do you grow an online business as the market shits the bed?” Focus on sales and marketing, stop reading social media. When the market shits the bed, people so often get panicked. We’re dealing with that with this whole COVID-19, that Coronavirus. People are all panicked and nervous, but you’re spending so much time being nervous and being panicked instead of being focused on sales and marketing, and focused on growth. When everyone else has panicked, be out there growing or focused on growing.

Martyn Cook said, “What guidance can you provide for digital communication to balance being assertive and not offending or upsetting, but still keeping the team in line?” For me, it’s over video. The reality is when you do written communication, you’re often going to be misunderstood or perceived in the wrong way. When you do it over a video, you have a much stronger chance of not upsetting people and getting the message across. I have been leveraging video highly for about fifteen years.

Donny Stark said, “What are C-level leaders doing consistently to be mindful leaders?” One is to remember that God gave us two ears and one mouth, and we should listen twice as often as we talk. Another one is to remember that everybody out there is struggling. Every single employee that we have, every single person that you encounter day-to-day is struggling with something in their personal lives. Being mindful of that is important. The last one is not over-scheduling yourself. I think C-level leaders, to be truly effective, should only book 5 of their 8 hours in a day and leave at least three hours open for interruptions, for growing people, for distractions. Over-scheduling can pull people out of mindfulness.

SIC 101 | Second In Command Q&A

Second In Command Q&A: More often than not, the COOs don’t want to be entrepreneurs, especially at least in the entrepreneurial organization.


Lauren McGinnis said, “In an economic slowdown, how close to the bone should a company terminate employees to ride out the storm?” I covered a bit of this in my book Double Double in chapter eleven, How To Grow When It’s Slow. One of the things I talk about is to focus on growth in sales and marketing instead of first focusing on cutting. It’s dangerous for anyone’s first reaction to be cuts unless you know that you need to make them or you’ve been riding too thin. I would be focusing my people on sales and marketing and trying to grow the business even during an economic slowdown. I would only be cutting the overhead positions and trying to keep all the revenue-generating positions as much as possible, and going back to those high-culture people. It’s almost like a hockey team that can play shorthanded.

Randall Hertz Sr. said, “How do you overcome and right-size what I deem a lingering culture, the negative residue of a management team that’s been replaced by you and your leaders?” It’s one by one making the cuts of the cultural cancers or the people that don’t fall in line with the new vision. It’s rolling out a vivid vision. Getting people excited about the vivid vision, keeping people that are excited about it, and getting rid of the people that aren’t. Being ruthless around deciding which people don’t fit and making those cuts.

Michael Fishman said, “Is valuation impacted by having a virtual staff?” I don’t have the experience on this, but I don’t think so. More and more we’re recognizing that being virtual as part of being a company. We’ve got a laptop, video, Slack and Asana. Why do we need to walk into an office and waste an hour a day, driving 30 minutes each way when we can be more effective with that 30 minutes having a life or working in the business? The proof is going to come right now when companies that can operate virtually through the storm that we’re in will be able to prove that it doesn’t hurt valuation at all.

Alex Yastrebenetsky has a company out of the Midwest in the US. It’s one of the top technology companies to work with called InfoTrust. I used to coach Alex and his cousin, Michael. He said, “What are the best questions to ask when interviewing a COO candidate?” What it is, is asking when they’ve done what I need them to do. It’s going through the core projects that I have on my plate that they’re going to have to be doing over the next twelve months and asking them to tell me when specifically they’ve already done those in the past, and digging into how they did them and how they grew. I also want to know how they grow people, but I don’t want theory. I want exact examples of when they’ve done the specific things. That’s more important than what the questions are and it’s more the type of questions. You’re looking to find out their pure experience on everything that you’re going to need them to do.

Mitch Tublin said, “How do you respond when your top sales closers start to strongly suggest policy decisions for the company? Some are commission related, but not all of them.” I would listen to them. A big opportunity is to listen to the salespeople and everybody in the organization. Sometimes the leader’s job is to listen and not speak. God gave us two ears and one mouth, so if we listened twice as often as we speak, there’s often nothing wrong with having salespeople give us good ideas.

Ed Ho said, “Do you want the CEO’s job?” More often than not, the COOs don’t want to be entrepreneurs, especially at least in the entrepreneurial organization. If I qualify this answer as companies from 50 to 500 employees, which is the COO Alliance members. If a company has 50 to 500 employees, more often than not, the second in command does not want the CEO’s job. They want to help make the CEO iconic. They want to help build the business. They’re often different personality profiles as well. We’ve had all of our members do a Kolbe A profile. The profile of the COOs and CEOs are drastically different. Often, they don’t want the CEO’s job at all.

Jill Johnson said, “What role should COOs play in assessing and working through strategic distribution?” I have never been in or around companies that work on distributions. I’m going to have to take a pass on that question. I can’t help you with that. Last one is from Gordie Bufton. He works on our team at the COO Alliance in recruiting, interviewing, and bringing on all of our great new members. He’s been setting records every month he’s been with us. Gordie’s question was, “What color are your toenails?” I started painting my toenails for fun, so they are dark navy blue. Thank you, everybody. I thought I would do an ask me anything. I hope it’s helpful.

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