When AuthorityGoes Wrong

Seven small drifts in the people who once asked the best questions in the room.

There is a particular founder I have been watching for somewhere close to a decade now. We met when she was running a business of perhaps 18 people, slightly underfunded, charmingly insecure about her own credentials, and reliably one of the most curious people I had ever encountered in a meeting. She asked questions one had to think about carefully before answering, paused for considerably longer than was strictly comfortable while she actually listened to the response, and seemed to operate from the cheerful assumption that almost everyone she met knew something she did not. Spending an hour with her was the kind of experience that quietly improved one's own thinking for the rest of the week, and she had no idea that this was the effect she was having on people because she was genuinely interested in the conversation.

The business is now perhaps four times the size it was then. She has acquired the various external markers one acquires across such a period, but she is still a fundamentally decent person, still the same woman underneath, still the founder I would describe to friends as one of the more impressive operators I know. But I would not describe her as curious anymore, something has happened to her in the intervening years, gradually enough that nobody has remarked on it, including me until quite recently, and I have spent the last eighteen months trying to articulate exactly what.

This piece is the result of that articulation, generalised across a number of founders I have watched undergo a similar process, with the specific details obscured to protect the various parties from being identified by their friends. What I have noticed is that the corruption of authority is made of seven small behavioural drifts that occur gradually in essentially decent people across the years they hold power, each of which is invisible from inside, none of which is corrected by the people around them, and all of which combine to produce a person who has become significantly harder to work with than she was a decade earlier, while continuing to consider herself, with perfect sincerity, the same person she has always been.

She is still a fundamentally decent person. She is also no longer the person she was, and nobody has told her, which is to say almost everybody has noticed and almost nobody has the standing to mention it.

❖The First thing to go is the genuine question. The founder I described above used to ask things she did not know the answer to, which is a more unusual quality in senior people than it sounds. Across the past several years, her questions have shifted register without her noticing, becoming the kind of questions that arrive with their preferred answer politely tucked inside them, looking for confirmation rather than information. She continues to experience herself as somebody who asks good questions, because she is still asking them in the grammatical sense, and the small change from inquiry to delivery is the kind of change that nobody mentions because mentioning it would require explaining the difference, which would itself be the kind of conversation that no longer seems welcome in the rooms she now occupies. The questions have not disappeared. They have politely converted themselves into statements that happen to end in question marks, which the team has learned to recognise and respond to accordingly, with the result that the meetings now produce considerably less new information than they used to.

The Second drift accumulates around her diary, which has become, across the years, a kind of structural fortress. She rarely complains about the density of her diary, although she occasionally observes, with a small tone of resignation, that she does not seem to have any unstructured time anymore, and would somebody please make sure her Thursday afternoons stay clear for thinking. The Thursday afternoons don’t stay clear, of course, because every meeting that has been added to them was added for a reason she herself approved at the moment of approval, and the cumulative effect of all the locally rational scheduling decisions is a diary in which she is now genuinely impossible to access except through the formally scheduled channels her assistant maintains. The corridor conversations that previously brought her small pieces of useful information no longer happen, because the corridor is now somebody else's territory, and the people who used to have the small useful conversations have either left or learned to communicate through formally scheduled briefings, which are not the same kind of conversation at all and do not produce the same kind of information.

❖ The Third drift is the slow disappearance of qualifying language, which is one of those changes that operates below conscious notice until somebody who has known the person for a long time happens to play back a recording of an old conversation and the difference becomes audible all at once. The earlier version of the founder used phrases like I might be wrong about this, my sense is, one possibility is, although I could be missing something. These phrases were not weakness markers. They were calibration markers, signalling that she was expressing a view that remained open to revision, and they made her significantly easier to disagree with productively because the disagreement did not feel like an attack on a position she was personally committed to. The current version of the founder uses essentially none of these phrases anymore. Her statements now arrive as confident assertions, and the team has adjusted its responses accordingly, with the entirely predictable result that disagreement has become a more delicate conversation than it used to be, and the conversations in which she might have been productively challenged on a misjudged position increasingly do not occur.

The quietly amusing version of this drift, which I have now witnessed in more than one founder, is that having spent years removing qualifying language from her own speech, she has become mildly impatient with colleagues who use it themselves. The qualifying language now reads to her as indecision rather than as appropriate calibration, and the speakers who use it are subtly downgraded in her internal estimation of the room. The colleagues, sensibly, have learned to stop using qualifying language in meetings with her, which removes the calibration markers from the conversation entirely and produces a room in which everyone is now confidently asserting positions that nobody actually holds with the certainty the language implies. The whole arrangement is held together by collective performance, and the founder is the only person in the room who has not noticed what is being performed.

❖ The Fourth drift is more difficult to describe because it operates as a slow narrowing rather than as a discrete shift. The people around her have changed gradually over the years, not because she has deliberately curated her social and professional circle, but because the calendar fortress and the long days have made certain kinds of relationships easier to maintain than others. The colleagues who once disagreed productively with her have either left the orbit entirely or settled into more comfortable patterns of agreement. The advisors who were retained for their contrarian instincts have either been replaced or have softened their contrarian instincts in response to the steady accumulation of small signals that contrarian instincts are no longer particularly welcome. The new hires were selected partly because they seemed easy to work with, which turns out to mean unlikely to push back, and they have lived up to that selection criterion with admirable consistency.

The cumulative effect of this narrowing is that she now operates with steadily diminishing exposure to genuinely challenging perspectives, while feeling, more strongly than ever, that she has a good handle on what most people think because most people, in her direct experience, do tend to agree with her. The two experiences are connected and she has not made the connection. She is not surrounded by sycophants, which is the dramatic version of this story. She is surrounded by reasonable people who have simply learned, through accumulated experience, that the version of themselves she finds most useful is the version that supports rather than disrupts whatever direction she is currently pointed in. The room has changed while she has remained in the same chair, and the change has been gradual enough that she has not had any specific moment in which to notice it.

She is surrounded by reasonable people who have learned which version of themselves she finds most useful.

❖ The Fifth drift is the one I find the most uncomfortable to write about, because it touches the small daily indignities that the team absorbs without quite remarking on them and that she does not appear to register at all. Her time has steadily become the only operational constraint that genuinely matters to her, with everyone else's time treated as essentially elastic. Meetings get moved at short notice because something more important has come up. Junior people are asked to wait outside her office for indefinite periods, which they always do, because the alternative is unthinkable for them and almost certainly invisible to her. The thirty minutes that had been promised becomes fifteen because of overruns elsewhere, which she handles graciously enough that the person who got fifteen minutes feels they should be grateful rather than slightly used. None of these is extraordinary in isolation, and she delivers each one with appropriate apology and recognition of the imposition, but the cumulative pattern reveals the underlying assumption, which is that her time is denominated in a currency that has slowly become more valuable than the currency the team is operating in.

The team continues to accommodate the pattern because complaining about it would be unproductive, which she interprets, with reasonable sincerity, as the team being relaxed about the arrangement. The team is not relaxed about the arrangement. The team is performing relaxation, which is a different and considerably more exhausting thing to maintain, and the founder is the only person in the building who has not registered the difference between the two postures.

❖ The Sixth drift is the most diagnostic of the seven, because the language a leader uses about her team in their absence is essentially uncoachable and reflects the orientation she has actually developed toward those people rather than the orientation she performs when they are present. The founder I have been describing used to talk about her early team with a generosity that was occasionally embarrassing to be in the room for, naming specific contributions by name, attributing the business's successes to the people who had delivered them, and treating her senior people as colleagues rather than as employees. She no longer talks about them this way. Individuals now appear in her account of the business in more generic terms, and the team has become my team in her speech, which sounds affectionate but signals a possessive relationship rather than a collaborative one. Specific contributions have become harder to attribute. Successes increasingly belong to the strategy rather than to the people who executed it. Failures increasingly belong to specific individuals whose names she can now suddenly remember in considerable detail.

The most diagnostic version of this drift is how she now speaks about a former member of the team after that person has left the business. The language she used about a particular departing senior person last year was subtly different from the language she had used about that person while they were still in the building, in ways that were not large but that I noticed and have continued to think about since. The departed person had become slightly less competent in retrospect, slightly more difficult to manage, slightly more responsible for the various things that had gone wrong during their tenure, and slightly less central to the things that had gone right. The downgrade was not dramatic. It was simply the small recalibration that occurs once the social conventions that previously required generous language no longer apply.  

❖ The Seventh and final drift, which I have come to recognise as the one that most reliably signals that the others have already done their work, is the small preoccupation with legacy that begins to surface in the founder's speech somewhere around the time she has built enough of a business to start imagining how it will eventually be remembered. The preoccupation is not unreasonable in itself. People who have built something genuinely significant are entitled to care about its memory, and there is nothing inherently corrupt about wanting one's work to be acknowledged once one is no longer doing it. The drift becomes problematic when the legacy concern begins to influence operational decisions in ways that prioritise the visible record over the substantive work. The initiatives that look good in retrospect.

The slightly curious feature of this drift is that the legacy fixation often arrives considerably earlier than would seem appropriate. Founders begin to worry about how they will be remembered at points in their careers when they have not yet accumulated enough of a contribution to be reasonably worried about it, which suggests that the fixation is being driven by anxieties about the present rather than by realistic concerns about the future. The founder who is securely satisfied with the substance of her current work tends not to spend much time worrying about how it will be remembered. The founder whose internal satisfaction is somewhat shakier finds the legacy question considerably more compelling, because resolving the legacy question is a way of providing the reassurance that the present substance is not quite providing. The fixation is, in this sense, less about the future than it appears, and more about the small inadequacies of the present that the leader is attempting to compensate for through anticipated future recognition.

❖ The seven drifts rarely arrive in isolation. They compound, with each drift creating the conditions that make the subsequent drifts more likely, until the founder is operating inside a steadily thickening behavioural pattern that is invisible from inside and entirely visible to anyone observing from outside. The calendar fortress prevents the corrective conversations that might surface the disappearance of qualifying language. The narrowing audience reduces the pool of people who might point out the language drift. The temporal collapse signals to the team that raising concerns about the founder's behaviour would not be welcomed. The seven drifts together produce a person who has become substantially harder to work with than she was five years earlier, while continuing to consider herself substantially the same person, which she remains in every way that matters internally and almost no way that matters externally.

The only reliable cure, to the extent that one exists, is the deliberate maintenance of relationships with people who knew the founder before she had any authority at all, and who have retained both the willingness and the standing to tell her when her behaviour is becoming difficult. These relationships are rare, structurally inconvenient, and almost impossible to construct after the drift has begun, which is why the founders who maintain them tend to have done so from the start of their tenure rather than acquired them mid-stream. The friend from twenty years earlier who continues to roll her eyes at the appropriate moments. The former colleague who left the business years ago and feels no current obligation to flatter. The family member who has known the founder long enough to refuse to be impressed. These relationships are the most undervalued asset in any senior career, because they are the only remaining source of honest signal once the rest of the environment has carefully adjusted itself around the founder's preferences.

A CLOSING OBSERVATION

I should say, before closing, that I am not entirely sure I am immune to several of the drifts described above, and I have not written this piece from a position of confident superiority on questions of character. I have written it from the position of somebody who has been watching the patterns operate in people I care about, and who has begun, with appropriate discomfort, to notice early versions of some of the same patterns operating in myself. The seven drifts are a mirror at least as much as they are a taxonomy. The most useful reading of the piece is the one that produces a small uncomfortable recognition somewhere around the third or fourth drift, at which point the reader has confirmed both the validity of the diagnosis and the difficulty of administering it to oneself. The founder I described at the beginning, in case anybody is wondering, has no idea I have been thinking about her this carefully across the past eighteen months, and I have no current intention of telling her, partly because I lack the standing the diagnosis would require, and partly because the conversation she most needs to have is not the one I am positioned to deliver. Whether anybody else is positioned to deliver it remains an open question, which is part of why the drift continues, in her and in many others, while the rest of us continue to perform the manners of the present moment.