May: The Supposed Nonplayers of Power

Core idea

Everyone plays — the only variable is the disguise

May is the inverse of April. April taught you to play the courtier game skillfully. May teaches you to recognize the people who claim they have opted out — and to understand that their opting-out is usually itself a strategy. Greene's central claim: there is no such thing as a person who has truly transcended the game of power. The behavior is universal; what varies is whether the player declares the game or denies it. The people who deny it most loudly are often the most ruthless players, because their declared innocence buys them moves the open competitor cannot make.

The toxic types are predictable

The bulk of May is a typology — a field guide to the recurring kinds of disguised player. The grandiose leader. The aggressive pleaser. The fake traditionalist. The unambitious front. The deep narcissist. The drama magnet. Each type has a stable behavioral signature, a stable set of moves, and a stable way of damaging the people around them. Greene's claim is that these are not personality quirks; they are recurring solutions to the problem of how to seek power while appearing not to seek it. Once you can name them, you can predict them.

Judge behavior, not words

The operative principle that runs through the whole month is judge people on what they do, not on what they say. Words are the medium of disguise. Behavior, especially behavior repeated across multiple situations, is the medium of truth. The kindly senior who has been quietly responsible for the departure of every junior who threatened them is not kindly. The egalitarian leader who has built a team of people who never disagree with them is not egalitarian. Greene's discipline is to track the pattern across years, ignore the explanations, and revise your model when behavior contradicts the stated character.

Why it matters

Misreading the disguise is the most expensive mistake in any organization

The cost of correctly playing the open game (April) is much smaller than the cost of being blindsided by a disguised player. The open opponent can be planned for. The disguised opponent operates behind a facade you have agreed to take at face value, and by the time you realize what has been happening you have usually already been damaged — your project killed, your reputation undermined, your alliances poached, your position weakened. May is a defensive curriculum. It is the cost of admission to the rest of the book.

The pattern repeats across centuries and contexts

The reason Greene's typology is useful is that it is genuinely time-invariant. The grandiose leader who needed a Versailles in 1670 needs a vanity podcast in 2026. The aggressive pleaser who built a network of obligation in a Renaissance court builds it now in a tech company. The fake traditionalist who invoked the founders to seize an institution did so in the Roman Senate and does so now in modern boards. The disguises update; the underlying moves do not. Learning the pattern once gives you a portable skill.

Key takeaways

Mental model

Copy sourceZoom

Practical application

Run the past-behavior check before trusting any new figure

When a powerful new colleague or partner enters your orbit, the single most useful diagnostic is to talk to people who worked closely with them in their last role. Not the official references — the people who left, the people they passed over, the people who reported to them. The pattern there is the pattern you will get. If five previous direct reports describe the same dysfunction in slightly different words, that is the truth, and the new charm being directed at you is the disguise.

Track the gap between stated value and revealed value

The cleanest signal of a disguised player is a persistent gap between what they say they value and what their actions reveal they value. The leader who talks constantly about humility but cannot tolerate a public correction. The colleague who claims to be a team player but whose every project ends with them as the sole credited owner. The senior who praises mentorship and yet has never produced a single successor. The gap is the data. Track it for ninety days and you will have a reliable model.

Don't try to fix the deep narcissist

May's most actionable advice is also its bleakest: the deep narcissist does not respond to feedback, therapy, time, or love. They have a stable structure that arose decades before you met them and will outlast every intervention you attempt. The correct move is not to fix them but to limit your exposure — minimize the surface area on which their behavior can damage your work, your reputation, and your equanimity. Greene treats this as a defensive skill, not a moral judgment. You don't have to hate them. You do have to stop pretending they will change.

Example

The "humble" CEO who couldn't tolerate a peer

Consider a CEO who is widely admired for their humility. They give the credit to the team, they speak quietly, they do not occupy the corner office. New executives joining the company are charmed by the contrast with the chest-thumping leaders they came from. Within eighteen months of joining, however, every executive who has been hired in at the senior-VP level or above has either left or been managed out. The explanations vary case by case — bad fit, performance issues, restructure — but the pattern across five years is unmistakable: the CEO cannot tolerate anyone in the building whose stature approaches their own.

This is the deep narcissist in modern dress. The humility is real as a self-image and false as a behavior pattern. The executive who has been studying May for years recognizes the signature in the first three months — the way disagreement is met with a soft sigh rather than an argument, the way the team is praised in the abstract and individuals are quietly diminished in private — and adjusts their plan accordingly. They either decline the role, accept it knowing they will likely be out in two years and treat it as a résumé credential, or stay short of the threshold at which they become a perceived threat. None of these moves are cynical. They are the application of a model that May provides and that the unprepared executive does not have.

Related lessons