I was not expecting a physical book.
It arrived on a Sunday — a long weekend, the kind where the days and activities blur together; the barbecues, the family time, the warm afternoons on the deck under the sun canopy. Not the kind of weekend where you’re watching the door for Amazon packages.
We thought the kids’ order had already come in on Saturday; as far as we were concerned, that chapter was closed. So when my husband appeared with another package addressed to me, his question was entirely fair: what did you order?
I had no idea.
He opened it. A book, he said.
I came out to the kitchen to find Cameron Herold’s The Second in Command: Unleash the Power of Your COO sitting on my counter — and I was genuinely confused. A couple of weeks earlier, I had come across Cameron Herold on social media and requested a copy through the COO Alliance. The confirmation email said he was sending one; nowhere did it say it would arrive as a physical book at my door.
I grabbed it, curled up on the sofa, and started reading. I did not stop for a while.
I read fast. That is not a boast; it is just how my brain works. A 240-page book with no technical density should take me somewhere around an hour.
The Second in Command took closer to five or six.
I had flipped through the contents and the appendices before I even reached the introduction — that is how I knew, before I was even properly into it, that this was a book I was going to read more than once. Chapter one, the seven types of COOs, got me immediately. I recognized myself; recognized roles I had held; recognized colleagues I had watched succeed and fail in second-in-command positions.
I got more than halfway through before I stopped, went back to the beginning, and read it again — highlighter in hand.
What kept stopping me was recognition — sometimes unsettling recognition. Things I had experienced and quietly filed away as me being weird, or wrong, or maybe just difficult — apparently not. I spent a lot of time reflecting. There was a freedom in that I was not entirely prepared for.
The book is positioned as a guide for CEOs — how to recognize when you need a second-in-command, how to hire one, how to work with one. That framing is accurate. But what it also does, without quite announcing it, is give the COO a mirror. And for a COO who has spent years doing this work without always having language for it, that mirror matters more than the author may have intended.
Before I had finished the first read, I was already building a list of people I wanted to send it to.
Reading from both chairs
The Second in Command is a CEO’s book. Herold is clear about that from the start, and he delivers: the book walks a founder or CEO through recognizing when they need a second-in-command, what kind, how to hire well, how to onboard thoughtfully, how to build a working relationship that holds.
But I read it from both chairs.
I am the founder of Northlight Advisory Services. I have also spent a significant part of my career in second-in-command roles — across nonprofit, professional services, and growth-stage organizations, at different scales, under different titles — but the same underlying function. I came to the book as someone who has lived on the receiving end of exactly the choices Herold is teaching CEOs to make. Some of those choices were made well. Some were not. The book was useful in both directions.
What it is quietly teaching CEOs is what to need from a COO. Which means that if you’re reading as an existing or aspiring COO, it tells you something more specific: what your CEO is being told to expect from you. That is more clarifying than a hundred articles written directly for COOs, because it names the relationship from the outside.
The person: what it actually takes
Before talking about what a COO does, it is worth talking about who a COO tends to be — because the role selects for something specific.
Herold observes early in the book that although COOs come in all shapes and sizes, they share some things in common: they work with a CEO, they are executing someone else’s vision, and they tend toward the practical rather than the visionary. They are, he notes, in high demand in a business environment dominated by founders and entrepreneurs who are long on vision and short on execution (p. 27). That framing is accurate as far as it goes — but I think it undersells what the role actually requires.
Being a COO is not simply about subordinating yourself to someone else’s direction. It requires genuine strategy and execution capability: the ability to take a vision and translate it into a roadmap, then constantly adjust the navigation as obstacles appear, new information arrives, and circumstances change. You have to be highly adaptable — but not so flexible that you cannot hold the line on truth, on mission, on values, when the wind shifts. The useful image I keep coming back to is one of trees. You cannot be an oak — too rigid, roots too fixed, and a storm will knock you down. You cannot be a willow — so bendable in every direction that you offer no resistance at all. A birch is closer to it. It sways. It absorbs. It dissipates the force of the storm by moving with it — and then it is still standing when the weather passes.
Herold writes that the COO needs “ego strength” — the ability to measure themselves only by results, without requiring public credit or affirmation (p. 177). That formulation is right, but incomplete. The ego question and the sense-of-self question are not the same thing, and the difference matters. The COO who functions well does not need applause, but they need to know precisely who they are and what they stand for. Without that anchor, the role will hollow you out. You can subordinate your need for recognition without subordinating your judgment. In fact, you have to. A COO who agrees with everything the CEO decides is not a COO; they are a very expensive yes.
My own formulation, arrived at over several years of doing this work: my wins are when the company wins. I have never been drawn to public recognition. If someone wants to tell me I did a poor job, they can do it in front of the whole room — it does not particularly bother me. Public praise, on the other hand, makes me uncomfortable. The satisfaction is in the working, not in being seen to have worked.
I am aware that is not a universal disposition. There are COOs who are very much public-facing — speaking, meeting people, building external relationships on behalf of the organization. That can work well. But it works when the CEO is deliberately inward-facing and has chosen someone to hold the external presence they do not want. The arrangement is still about fit. If you crave visibility, you need a CEO who emphatically does not want to be on stage. The pairing carries the logic; the individual disposition does not have to match a single template.
What does hold across most pairings: the COO is often making the thing possible without being the person who is seen to have made it possible. Someone who genuinely needs to feel seen in order to keep going will struggle with that — not because they’re wrong to need it, but because the work often will not give it to them. The CEO gets the stage. The COO makes sure the stage does not collapse. That arrangement has to feel like enough. If it doesn’t, the work will cost more than it gives.
There is also an asymmetry in the relationship that Herold describes carefully but that I think is worth stating plainly. The CEO can be vulnerable to the COO in ways the COO cannot always reciprocate upward. The CEO can admit doubt, fear, the shape of a risk they don’t know how to name yet — and the COO holds that. The COO may have doubts of their own, but expressing them upward carries different weight. The relationship is close, sometimes unusually so. It is not, however, symmetrical. Understanding that and building honestly within it is part of the work.
The function: hard to define, easy to recognize
The title is almost beside the point.
COO, VP Operations, Director of Operations, Chief of Staff, Director of Administration and Operations — the same function shows up under all of these. In smaller organizations it may not have a formal title at all. What matters is not what is on the business card. It is whether someone is holding the operational reality of the organization together and creating the conditions for others to do their best work.
Herold’s framing of the role as complementary — not subordinate — is one of the book’s most useful contributions. The COO is not a junior CEO waiting for their turn. They are a different thing entirely: someone whose strengths fill the gaps in the CEO’s, whose read on the organization is different, whose relationship to risk sits in a different place. The CEO asks what if we could? The COO asks what would it actually take? Both questions are necessary. Neither is lesser.
The breadth of the role is real, and it is part of what makes it hard to explain. Finance, marketing, technology, operations, people — the effective COO does not need to be the deepest expert in any of these. They need enough fluency to ask the right questions, recognize when real expertise is required, and create conditions in which specialists can succeed. The job is not to know everything. It is to know how to find out what matters and who can solve it.
The partnership, when it works, runs deeper than most professional relationships. I worked alongside one CEO for several years. We commuted together most days — not structured meetings, just time in a car. That unstructured space was where a lot of the real alignment happened. Throughout that partnership, I could write something that he would think he had written himself — probably helped by the fact that we had known each other long before working together. Not because I was mimicking him; because I understood how he thought, what he cared about, what he would say yes to and why. That kind of alignment is what allows two people to cover different sides of the same room without constantly checking on each other. It is not fast to build, and it cannot be manufactured.
The work: systems that outlast you
Herold is direct about something most people prefer not to say out loud: the CEO-COO relationship is rarely for life. It is unlikely a single COO will be suitable for all phases of an organization’s growth (p. 203). To stay in the same job, a COO’s skill set has to continue matching the organization as it scales — which is often a challenge (p. 204). His rough heuristic: most senior people can only take a business through two doublings in revenue before the third double makes it hard to continue (p. 205).
The thread I pull from that is my own: what you are really doing, if you are doing the job well, is working yourself out of the role. Not out of a job — out of the role as it currently exists. If the organization grows successfully, its needs change. The COO who takes a company from one stage to the next may not be the COO it needs for the stage after that. That is not a failure; it may be the clearest measure of how well the first job was done.
I know this from experience. I was part of an organization through two significant growth phases. I was good at what I was brought in to do. And when the organization changed underneath me, I could see — clearly, without a great deal of self-deception — that I was no longer the right fit for what came next. I probably should have left. The timing made that difficult. So I stayed, in a title that was no longer quite the job, doing much of what I had always done without the formal authority that had made it possible. People still came to me with problems because they trusted my judgment, even when the org chart no longer routed through me. Institutional memory has a long shelf life, even when your formal role does not.
The shadow COO situation is more common than people talk about. After my title changed, I was no longer in the role — but the systems I had helped build were still running, and so was the knowledge of why they worked the way they did. When a team needed to think through a new process, they came to me. When something wasn’t working in a system, they came to me. Contracts that needed reviewing, questions about potential partnerships, how to frame something for a board package — all of it found its way to my desk, regardless of what my desk was now officially for. Officially, I had a new and narrower mandate. Unofficially, I was still building systems with teams across the organization, still helping people think through problems that were not in my new job description but had very much been in the old one.
Was it sticky at times? Yes. But I understood why it happened, and I did not resent it. I had built those relationships by putting the team first — by believing in servant leadership not as a concept but as a daily practice — and people remembered that. When they needed help, they went to the person they trusted to show up. The title had changed. The trust had not.
Servant leadership has a substantial body of literature behind it — the Greenleaf Center for Servant Leadership is the canonical starting point.
What I took from that experience — and from this book — is that the systems are supposed to outlast you. I have a personal practice of going offline for the month of December every year. December works for this partly because the pace of new business naturally slows; the month is mostly about wrapping up, finishing what is in motion, and preparing for the new year. But the point is not the timing. The point is that everything the organization depends on has to run without me.
The team members who were still in place — those not yet on their own holiday time — knew what to do and how to do it. They had the tools. They had the authority. They knew who to contact, how to put a package together, how to keep things moving. When I came back in January, we could go straight into a proper review: what had gone out the door, what was ready to go, what needed attention. Teams were already on the same page. Stakeholders had been kept informed. The work had not waited for me.
That is the test. Not whether you can stay on top of things — any capable person can stay on top of things. The test is whether the people you have grown, and the systems you have built, can operate without you in the room. If they cannot, you have not built something. You have built dependency, and eventually that dependency will be a problem either for the organization or for you. The COO’s job is to increase the capacity of an organization to function without their constant presence — to grow people who can solve their own problems, to create structures that do not require intervention at every turn, to leave something that runs when you are gone. That is a different model of leadership than becoming the organization’s indispensable problem-solver. It is also considerably harder.
It is not coincidentally the most direct connection between COO work and fractional COO work. When you come in for a season, the systems have to be able to run when you leave. If they cannot, you have not done the job.
Where the book gets complicated
Herold occasionally reaches for relationship metaphors — the CEO-COO bond likened to a marriage, with date nights recommended — that I understand in spirit but that do not translate universally.
The closeness is real. I am not disputing that. But the framing carries an exposure the book does not address: in organizations where bad actors exist, or where backchannel speculation travels easily, the language of romantic intimacy creates ambiguity around a relationship that already requires careful management. The CEO and COO can build real trust, laugh together, talk about their families, become friends. That is fine. But call it what it is: relationship building. Not date night. The underlying idea is sound; the metaphor is doing unnecessary work and occasionally creating the wrong kind.
The COO Alliance also surfaces repeatedly throughout the book in ways that occasionally feel more promotional than editorial. To be fair, it does have its own section — Herold is not hiding the affiliation. But it also appears as brief interjections mid-argument, which interrupt the flow at moments when the content is at its most useful. And when Herold reaches for a worked example to illustrate the Vivid Vision concept (pp. 161–166) — a genuinely valuable framework for how CEOs communicate direction — the example he uses is the COO Alliance itself. I understand the impulse; you write about what you know. It just lands a little funny when the example of an aspirational organizational vision is the author’s own organization.
These are not reasons not to read the book. They are reasons to read it as a practitioner reads anything: with appreciation for what is earned and appropriate skepticism about what is selling.
Who should read it: If you are a CEO, founder, or executive director considering anyone who will operate in your close circle — a COO, a fractional executive, an operations manager, even a strong executive assistant — this is a book you really should read before you make that hire. Do the activity inventory (ch. 3, p. 77). Understand what you are genuinely willing to give up. Hire toward your gaps, not your comfort zone. A COO who can do what you can already do is not a COO; they are expensive redundancy.
If you are an existing second-in-command, read it to understand what your CEO is being taught to expect from you. You will find things in here that explain partnerships you have been in — the good ones and the difficult ones. If you are considering doing this work fractionally, read Chapter 10 with particular care: the part about recognizing when the right COO for this stage is no longer the right COO for the next is the most honest thing in the book, and it has direct implications for how you think about the work you come in to do.
Verdict: One of the few books that earns a genuine recommendation — not because every sentence is perfect, but because it gives unusually clear language to a role that is almost always poorly defined. I have already recommended it to people on both sides of the relationship.
If you want a shorter take or are looking for where to get a copy, I also wrote a standalone review.