Cameron Herold, The Second in Command: Unleash the Power of Your COO (2023)
I signed up for what I thought was a digital download. A couple of weeks later, a physical book arrived at my door on a Sunday afternoon of a long weekend, the kind where the days blur together, and nobody is watching for packages. I was pleasantly surprised, and then I curled up on the sofa and started reading.
I do not often recommend books. Reading is personal; what lands for one person slides right off another. The Second in Command crossed that threshold. By the time I finished the introduction, I knew I’d read this book more than once. I got more than halfway through before I stopped, went back to the beginning, and read it again, highlighter in hand.
At its core, The Second in Command is a CEO’s guide — how to recognize when you need a second-in-command, how to find and hire the right one, how to onboard them, and how to make the relationship work. Cameron Herold is clear about that framing and delivers.
But the book also does something it doesn’t quite announce: it gives the COO a mirror. I have spent years working in second-in-command roles — different titles, smaller organizations, the same function. For someone who has done that work without always having language for it, that mirror matters more than the author may have intended.
I found myself agreeing with Herold a lot as I read.
Before a CEO hires a second-in-command, Herold asks them to do an honest inventory — mapping their own tasks by competency level, from things they do poorly to things only they can do. The point is not to catalogue weaknesses. It is to understand what the CEO is actually willing to give up. Hiring a COO and then refusing to cede ground is not a partnership; it is a performance. The COO needs real space to do the job, and the CEO has to be genuinely ready to create it.
The relationship is not incidental to the role — it is the role. Your COO is your person; the one you call at midnight, the one who shows up without needing the full explanation. That relationship requires trust, honest communication, and real rapport. It also requires being clear-eyed about what it is: it is not necessarily reciprocal, and probably should not be. The CEO can be vulnerable to the COO in ways the COO cannot always reciprocate upward. Understanding that dynamic — and building honestly within it — is one of the more useful things this book offers.
The title is almost beside the point. COO, VP Operations, Director of Operations, Chief of Staff — the function matters more than what’s on the business card. You may be more hands-on in a smaller organization and more strategic in a larger one, but the good second-in-command needs to move between both. Herold’s framing of the role as complementary — not subordinate — is one of the book’s strongest contributions.
The COO, Herold argues, does not need to be the deepest expert in any domain. Finance, marketing, technology, operations, HR — the effective second-in-command needs enough fluency to ask intelligent questions, recognize when real expertise is required, and create the conditions in which specialists can succeed. The COO’s job is not to know everything. It is to know how to find out what matters and who can solve it.
And then there is the idea that stopped me cold: a good COO should work themselves out of the role. If the organization grows successfully, its needs change — and the strengths that took a company to one stage may not be the strengths it needs for the next. A COO who has done their job well may eventually become the wrong COO for what comes after. That is not failure. It may be the measure of success.
That is not to say I agreed with everything. Herold occasionally reaches for relationship metaphors — the CEO-COO bond likened to a marriage, with date nights recommended to maintain it — that I understand in spirit but that do not translate universally. The closeness of the relationship is real; I am not disputing that. But in practice, that framing carries an exposure the book does not address: in organizations where bad actors exist or where backchannel speculation travels, the language of intimacy becomes material. The COO Alliance, meanwhile, surfaces several times in ways that feel more promotional than editorial. The network is likely excellent; it deserved a dedicated section rather than brief interjections that interrupt the flow mid-argument.
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 — read this book before you make that hire. Do the inventory. Hire toward your gaps, not your comfort zone. If you are an existing second-in-command, read it to understand what your CEO is being taught to expect from you. It will tell you more than you expect.
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.
Get a copy: Free physical copy via COO Alliance · Order from Cameron Herold’s site · Amazon Canada