A Note on the Second in Command Problem

If you have lost two or three good number twos in a row, I suspect you have been telling yourself a particular story about why, and the story has probably involved the specific personalities of the people who left, the specific timing of their departures, the specific competing offers they received, or the specific stage of the business that happened to coincide with their decisions, and the story has probably been composed from a reasonable combination of facts that are individually true and that collectively do not quite add up to what is actually happening, which is why I have decided to write to you about this, in the hope that it is useful, and in the full awareness that writing about it to anyone else is considerably easier than writing about it to oneself, which I have had cause to notice.

The pattern you are inside, if you will allow me to describe it from the outside, is almost always the same pattern regardless of which specific personalities have been involved in the recent departures, which is itself the first clue that the pattern is about the role rather than about the people who have been occupying it. The number two in a founder-led business is one of the structurally hardest positions in modern professional life, because the role requires simultaneously carrying the operational authority to run the business day to day and the political humility to defer to a founder whose relationship to the business is categorically different from any employee’s relationship could ever be, and the combination of operational authority and political humility is extraordinarily difficult to maintain in a single person for more than about two years without one of the two eroding, usually the political humility, because operational authority grows naturally through doing the work while political humility requires constant renewal through conscious self-management.

What tends to happen, in the specific pattern I would like to describe to you carefully, is that the number two arrives with high levels of both qualities, performs beautifully for the first twelve to eighteen months, begins somewhere around month twenty to feel that she has earned more operational authority than she is currently being granted, and by month twenty-four is operating with a quiet daily friction against the founder that she is managing professionally but that is slowly depleting the reservoir of political humility she arrived with, which she experiences, from the inside, as the entirely reasonable realisation that she now has a stronger operational grasp of certain parts of the business than the founder does and that the founder is slightly in her way. The founder, from her side, is experiencing the same period as the gradual realisation that the number two is becoming slightly difficult to manage and that the collaborative relationship of the early period has shifted into something subtly more oppositional, which the founder experiences as the number two having overreached rather than as a predictable consequence of a role that was always going to produce this tension.

Both of you are, of course, correct about what you are observing, which is one of the quieter cruelties of the arrangement. The number two has indeed developed a stronger operational grasp of certain parts of the business than you have, because she has been running those parts of the business while you have been running the business at large, and the specific knowledge accumulates in the specific role. She is correct that she has earned more operational authority than she is being granted. You are correct that she is becoming slightly difficult to manage. Both observations are accurate. The difficulty is that neither observation leads to a resolution that either of you is prepared to accept, which is why the relationship frays, and why she eventually leaves, and why the next number two will arrive with high levels of both qualities and will begin the same cycle, and why you will find yourself writing a similar farewell email somewhere around her month twenty-eight, which will be composed with real warmth and will privately feel like the fourth time you have written it, which it will be.

The honest version of what is happening, which I would offer to you gently because I have watched this pattern operate in people I care about and because I have no interest in making this worse than it already is, is that the problem is not that you have been unlucky with your number twos and it is not that the people you have hired have been personally flawed, although both of these are the stories that are easiest to tell and both of these contain enough truth to make them tempting to continue telling. The problem is that you have not yet made

the structural decision that the role requires you to make, which is the decision about what you are actually willing to give up in exchange for having an effective second in command, and until you have made that decision honestly, the number two role will keep producing the same pattern, with slightly different casts, and the slightly different casts will keep leaving.

The decision is not primarily about compensation or title or reporting lines, although all three of those are frequently the proxies through which the actual decision gets avoided. The decision is about operational authority. You have to decide, in advance, which specific decisions you are willing to let your number two make without consulting you, and you have to make that decision with enough clarity that she knows exactly what her authority is and you know exactly what you have given up, and you have to hold to it even when she makes decisions you would have made differently, because the moment you override her on a decision that was supposed to be hers is the moment the political humility reservoir starts draining faster than it can be refilled, and the countdown to her resignation begins quietly in the background without either of you noticing it has started.

I am aware that this is uncomfortable to read, partly because it suggests that the pattern is not accidental and partly because it suggests that the correction is not primarily about hiring better candidates, which is where most of us would prefer the correction to be located. I am also aware, from personal experience, that making the structural decision I am describing is considerably harder than it sounds, because the decision requires giving up specific aspects of operational control that you have become attached to, and the attachment is almost always greater than you have been willing to admit to yourself, which is why the decision has been postponed, which is why the number twos have been leaving, which is why I am writing to you now.

What I would suggest, if you are willing to take a suggestion from somebody who is still working on this herself, is that before you hire the next number two you spend an uncomfortable afternoon writing down the specific decisions you are willing to let her make without your involvement, and that you share the list with her on her first day, and that you commit, in a way that will cost you something to break, to not overriding her on any of those decisions for the first twelve months, regardless of how strongly you feel about the specific choice she has made. This is not a complete solution, because no complete solution exists for a structural tension that is inherent in the role, but it is the mechanism I have seen produce the longest number two tenures across the founders I have known, and it is the only mechanism I have seen produce them with any reliability.

I hope the next time you have cause to write a farewell email it will be the one you write when she retires, with your business having grown in ways that would not have been possible without her, and with you still friends afterwards, which is the version of this story I would like for you and for her and for everyone who comes after her into this particular role.