When the Trusted Advisor of the CEO is a Fool

Epichtonius Cosmopolites, The Fool’s Cap Map of the World, ca. 1580s*

A trusted advisor sometimes emerges when the CEO feels that even senior executives tend to speak their minds ‘selectively’ and are more likely to tell him what he wants to hear rather than what they themselves are thinking. Indeed, how can the CEO succeed at his task if he cannot get honest and constructive feedback from at least one trusted critical stakeholder?

Who are the trusted advisors?

Trusted advisors of CEOs are usually experts at some trade or craft, meaning that they have prolonged and worthwhile experience through practice and education in a particular field. They are widely recognized as a reliable source of knowledge, technique or skill.

Some of them like to brag of having successfully managed more than 30% of the M&A they have carried out.

They usually have traveled around the world for business and pleasure.

They often hold a MBA from a renowned business school.

Few of them are professionally trained in the domain of human behavior.

Even fewer are poets.

Occasionally, regardless of their specific expertise, some trusted advisors of CEOs also seem to be inhabited by The Fool.

The archetype of The Fool

The archetype of The Fool, interpreted as an universal symbol of psychic energy, revealing shared roles among various societies (Jung, 1947), has inspired generations of “wandering knights” (Chevalier & Gheerbrant, 1973, p. 196), creative and playful individuals, not bound by any fixed ideology, rejecting appearances and even contemporary morality, continually on the move, free from current taboos, holding unexpected potential and endlessly expanding their boundaries (Jodorowsky & Costa, 2009).

The Fool represents a full spectrum of characteristics that can manifest themselves in specific situations, and contrary to a stereotype that limits possibilities, the archetype of The Fool empowers them (Pearson, 1989).

The Fool is fire energized by the wind (Taleb, 2014, p. 3): The Fool seems to thrive and grow when exposed to chaos, randomness and uncertainty, The Fool is beyond resilience and robustness, The Fool is antifragile. When the resilient resists shocks and stay the same, the antifragile gains from disorder and gets better (Ibid.).

What do the trusted advisors inhabited by The Fool do?

When inhabited by The Fool, the trusted advisor “travels” beyond rationality, exploring conscious thoughts while being attentive to interrelated unconscious drives, wandering to get outsight with an attitude of empirical skepticism and a floating attention. He takes a step back, asks questions, reframes questions and confronts the obvious. The trusted advisor says out loud what it is somehow already known, but what no-one could or would dare to say.

Speaking his mind while showing some empathy — meaning he’s able to be distinct without being distant, and able to create and offer space for the other to be fully himself — the trusted advisor confronts the CEO without him loosing face; he loses face for him.

When the time is right, the trusted advisor also dares to address the issue of ethicality (which refers to propriety, i.e. what is proper and fair) and reminds the senior executive of the importance of choices, not solely the importance of decisions. If decisions are about information, choices are about identity: Who do you wish to be, Sir? (Rangan, 2015)

At his best, the trusted advisor brings some balance by gently offering a mirror to his interlocutor, at a safe distance, to help him look beyond projections, conventional beliefs and artificial limits. As if in contact with some poetic energy, the trusted advisor becomes “the middle of a proof” (Pey, 2018, p. 173) and some outsight gets transmuted into insight, acting out is replaced by reflection.

“For the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.” — Steve Jobs’ Stanford Commencement address, 2005

By his sole presence, the trusted advisor shows the CEO that all winners need losers, all sages need fools and all “good-doers” need “bad-doers”, and that they are both interdependent, like the poles of the same magnet.

When inhabited by The Fool, the trusted advisor fosters self-awareness.

More often than not, to improve the communication flow with the CEO, the trusted advisor uses humour, through which they “engage in a form of “deep” play dealing with fundamental issues of human nature such as control, rivalry, passivity and activity. Working through what can be destructive fantasies creates a soothing effect which can eventually redirect the organization toward reality issues.” (Kets de Vries, 1990, p. 767)

Humour also helps the CEO and his trusted advisor to remain anchored in humility, to avoid as much as possible getting contaminated by arrogance or even possessed by hubris, the disease of power that causes blindness; as Robert Anton Wilson (an underground science-fiction novelist and for a short period of time an associate editor for Playboy Magazine) used to say: “If the world seems to be getting bigger and funnier all the time, your intelligence is steadily increasing. If the world seems to be getting smaller and nastier all the time, your stupidity is steadily increasing.” (Wilson, 1980, p. 137)

Not shy to express affectionate cynicism — “an attitude and an atmosphere that cools off human conflicts more effectively than any amount of physical or moral violence” (Watts, 1966, p. 134), the trusted advisor occasionally reminds the CEO of Aristotle’s witty wisdom, that the ultimate goal of action is contemplation — knowing and being rather than seeking and becoming (Watts, 1966, p. 137).

While interacting with the CEO and focusing on him, the trusted advisor simultaneously keeps an eye and an ear on the organization as a whole, attentive to the human forms of interaction that bring it to life. The trusted advisor “feels” the corporate culture, he can “smell the place” (to refer to Professor Sumantra Ghoshal’s famous speech at the World Economic Forum).

And when invited to the executive diner table, as if he were trying to entertain his audience, the trusted advisor often “juggles” with circular questions, to elicit various perspectives within the group, creating connections (broadening the understanding of the context) and distinctions (narrowing the focus when generalisations predominate). New information eventually emerges before dessert time, and new ways of viewing problems, the context and its challenges are encouraged, and therefore potential changes of functioning (Brown, 1997).

How to spot a trusted advisor inhabited by The Fool?

Humble and shameless at the same time, the trusted advisor inhabited by The Fool seems to have — although in the Age of Instagram — no pleasing and easily identifiable “filter”.

In memory of the medieval court jester who bore a grotesque shape — his body standing as a living symbol of imperfection arousing laughter — the trusted advisor appears at least slightly “marginal”. Generally a “low” character, not necessarily in terms of hierarchical status, not necessarily in terms of physical appearance or social background, the trusted advisor usually holds at least some of the contemporary stigmas of the corporate world. At the very least, when senior executives tend to wear Brioni suits, the trusted advisor could be spotted in his odd appearance or levity, pairing tailored baggy jeans with funky colorful washed-out socks and wearing a skull ring engraved with a mysterious quote, which could eventually become the symbols of his institutionalized role, such as the court jester’s cap and scepter (Kets de Vries, 1990, p. 759). Dressed up as such, he’s easily identified, categorized, sometimes mocked and despised contemptuously by the corporate crowd, usually cast as a non-threatening non-conformist; he can eat his lunch quietly in the cafeteria.

The trusted advisor holds no ambition within the corporate court and this can reassure the corporate power-trippers that his words are unlikely to be geared to his own advancement (Otto, 2001, p. 245). He does not stand “in the light” of the corporate stage — he is a being of the “shadows” — and does not compete with the performers of the corporate world. To be out-of-competition also protects him from common corporate envy.

The trusted advisor has to be sane and healthy enough though, to cope with peer pressure, to recognize and accept his own foolishness and marginality, to be able to deal with inner violence and tensions, desires, fears and contradictions that inhabit the corporate world and himself as well. It’s a tricky play and the risk of ending up burned out alive at the stake is always present.

Internal outsider or outsider from outside?

In some organizations, the trusted advisor is found on the payroll as an official “Strategic Board Advisor”, or sometimes disguised as a young seductive Financial Analyst, or even as the Personal Executive Assistant. As such, the internal trusted advisor is not dependent of future consulting fees and sometimes does not even have to generate money. He is an “outsider on the inside” (Otto, 2015, p. 568), an undercover ethnologist who has been imbued with the corporate culture for years, and whose internal network is filled with diversity, spreading across the whole organization. The trusted advisor did not came “into” the organization, he came “out of it”, as a leaf from a tree. The internal advisor truly cares about the organization to which he belongs.

In those organizations, the CEO is suspicious of external consultants, concerned that they would behave merely as tourists, visiting the corporate culture for souvenirs and hunting trophies (nowadays, according to a recent study conducted by the Egon Zehnder CEO Practice, most CEOs seem to prefer having a “trusted lieutenant” on board (44%) than turning to an external consultant (15%) to get truly honest feedback (Najipoor-Schuette & Patton, Spring 2018)).

Other organizations feel more at ease with an “outsider from outside”, the professional bounty hunter holding a “Visitor” badge, the critical cosmopolitan with an exotic twist, especially when he is self-confident and successful enough that his life does not depend on a single client. The reassuring external advisor entertains a wide heterogeneous network, he’s able to connect not solely with diverse individuals but also with diverse organizations, to multiply knowledge and gain new perspectives on the current state of the world.

In those organizations, the CEO is wary of internal consultants, concerned that they would be “too close to the fire to keep a cool head”, that they would be too difficult to “manage” if they become too disruptive, or that they would just become useless if they end up expanding the ranks of the sycophants’s court.

An intense and delicate relationship

The trusted advisor has faith — in life, in other people, in the CEO, and in himself — and this is the attitude of allowing the spontaneous to be spontaneous, in its own way and in its own time. The trusted advisor embodies the possibility of mutual trust, the alternative to a totalitarian police-state, in which spontaneity is virtually forbidden (Watts, 1966).

Whether internal or external, the trusted advisor is loyal to the CEO, at the service of the CEO, but not an obedient servant. Occasionally, the folly’s coefficient attached to the trusted advisor exasperates the CEO, leaving him feeling like he is being bothered by a sanctimonious mosquito. It cannot be otherwise. For sure, the CEO is sometimes tempted to fight or to take flight from his advisor, to eliminate this seemingly “agent of chaos!” (The Dark Knight, 2008) he once allowed in his court, as to eliminate certain realities from his awareness; at the same time, he can’t ignore that this too is a fantasy, and that it would be foolish to try to eliminate reality. As written on Sigmund Freud’s memorial in Vienna: The voice of reason is small, but very persistent. Maybe, it is when the CEO realizes that the main threat is inside himself, that there is no enemy out there, but only within, that it will be possible for the organization to truly deal with frustration and anxiety constructively (Hendrikz, 1999, p. 4).

The relationship between the CEO and his trusted advisor is intense and delicate, like every genuine relationship, and as long as the CEO feels safe in his presence, the trusted advisor is safe, and reciprocally.

… When you say / That we must walk with those who build the spring / To help them not to be alone / And not to be alone yourself / In your tower of stone / Devoured of ivy / I give you reason / And when you say / That we have no reason to be / Only for other beings / You are right you are right / And when you say / That the world must be sung to transform it / And to explain it and to save it / And to live not only in a soap bubble / But in hatred of injustice / And for a purpose embodied like a cornfield / You are right you are right… — Paul Valet, 1949**

The relationship of the CEO with his trusted advisor is intense and delicate, because it is based on a love of truth.

Note: For ease of reading, the masculine form is used throughout the text to designate the trusted advisor and the CEO, but may refer to many different gender identities, including male, female, transgender, gender neutral, non-binary, agender, pangender, genderqueer, two-spirit, third gender, and all, none or a combination of these.

* The Fool’s Cap Map of the World is one of the enigmas of western cartographic history. Measuring about 14 inches by 19 inches and printed with a copper-plate engraving, the map is thought to date from the late sixteenth century. Although Epichtonius Cosmopolites appears to be the artist’s name, it translates roughly as “Everyman,” leaving the true identity of the mapmaker a mystery. Some scholars attribute the map to a little-known Christian sect called the Familists, who valued self-reflection and, ahead of their time, the idea of the world citizen. The uncomfortable truth that the map seems to tell us is that the world is an irrational and dangerous place, and quite literally, a foolish place. This is underlined by the mottoes of biblical and classical origin, dotted across the map. The Latin quote just above the map is from Pliny the Elder: “For in the whole universe the earth is nothing else and this is the substance of our glory, this is its habitation, here it is that we fill positions of power and covet wealth, and throw mankind into an uproar, and launch wars, even civil ones.” The reason for so much trouble and strife appears to be explained in a quote from Ecclesiastes: “Vanity of vanities, all is vanity”. Over the cap, we can read the Latin version of the Greek dictum: “Know thyself” (Hulme, 2018; Jacobs, 2010; Turnbull, 2000).

** Paul Valet, a resistance fighter during the Second World War, gave up his life as a concert pianist to become a medical doctor in the southern suburbs of Paris, a discrete poet in which frenetic lyricism and serene reflection coexisted, praised by his peers, Éluard, Prévert, Char, Michaux, Cioran, suffering from nervous and cerebral disorders, was admitted to a psychiatric hospital before dying on February 1987, Paul Valet was his pseudonym, he wanted to be “at the exclusive service of poetry”.


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