The demise of the court jester and why it matters

Everyone knows what a jester is – the clown in the funny hat who is there to make people laugh and entertain the court while they feast with the king. But as with so much today this is a shallow misunderstanding which misses the significance of the role and its value to those in power – the humour was a tool; the entertainment was the box it came in.

The role of the jester was the deliberate creation of a protected role with intimate access to the greatest power in the medieval world. Although the modern perception of the jester as a comic fool tends to place them in medieval Europe, the role has existed since 2100BCE in Egypt and endured through the Roman Empire and centuries of Chinese imperial dynasties before becoming more formalised in the courts of medieval Europe. No laws protected the jester from royal censure. The convention of the “Jesters’ Privilege” did – a convention that allowed the jester much more latitude than was given to the rest of the court. It allowed one person to say what others could not. It allowed the most powerful person in the land to hear the unvarnished truth in a way that gave both sides the safety of psychological distance. The use of humour to soften the delivery of a difficult message, permitted by a convention that specifically allowed it to happen. Not accident or tolerance on the part of the king. Not suicidal bravery on the part of the jester. Both parties understood their roles in a delicate and important balancing act for the benefit of the whole organisation. Henry VIII threatened to kill his jester Will Sommers on more than one occasion but never did – for a monarch not unwilling to make bold and fatal decisions on the spur of the moment, it is a mark of how much the Tudor king valued the sharp eyes and sharper tongue of his jester.

The jesters were at the court, but not part of the court – they were not competing for advancement or favour and therefore were no threat to either the king or the nobles. As a result, the courtiers could hear the criticism in a way that would have been impossible had it come from another member of the court. The structural independence was as important to the influence of the jester’s words as any royal protection. Archibald Armstrong was expelled from the court of Charles I for one too many jibes at the Archbishop of Canterbury –the move from observation to opinion compromised his independence.

The English Civil War brought an end to the custom in England – when the monarchy was restored in 1660 the role of the jester was not. The role of truth-telling moved to the stage, gaining a wider audience but little access to the ears of the powerful. More importantly, without the structural protection and agreement of the role, what had been caustic observation designed to open the eyes of the monarch now became the criticism of an outsider – ill-informed and easily ignored.

Today most absolute monarchs are gone yet there are more individuals (or small groups of people) who can change the shape of the lives of thousands or millions of people. In a world of curated information, tailored algorithms and major incentive packages very little has really changed for the powerful decision-makers. They still act on incomplete and flattering information, filtered through layers of increasingly rose-tinted glass until the most egregious decisions actually make sense if you only have access to the curated information and flattering reinforcement that they receive from their “court”. The best decision-makers recognise this tendency, acknowledge the fact that power corrupts not just the powerful but those around them, and put steps in place to mitigate this damage. While they might no longer wear a costume or a hat with bells, the easily-identifiable role of an acknowledged and protected truth-teller still exists in a few places, although you may have to look closely to find them.

The Non-Exec Director on the board who insists on representing the interests of the company and the customers long after the C-Suite wish they would stop. The senior Individual Contributor in an AI company who now finds the ethical issues and forces them into the open to be discussed and picked apart rather than being quietly fixed to protect the quarterly earnings call. The Critical Friend who, in the aviation sector is specifically employed to provide the red-teaming of major safety decisions and doesn’t have to worry about the career consequences of always being the Debbie Downer – that is their career.

I’ve been fortunate enough to fill that last role for a number of years in a number of different organisations. I work in a world that provides the career structure to support it (staying flying at the expense of promotion, so you aren’t a career threat to the leadership). The longevity means that you build trust with people in positions of authority over years or decades – for a few years I had taught or gone through training with the entire Exec team!  There is a huge freedom in being the person whose career path sits them outside of the normal structure, allowing privileged access to the decision-makers and the ability to speak your mind. But this comes with a significant responsibility to be the one who speaks up when it is most uncomfortable, who presses the point when others have let it drop as too difficult, or who sometimes refuses to be anything other than the pain in the ass that an organisation needs.

It's lonely, frustrating, difficult and indispensable. There is precious little praise or recognition in it, in fact I have been at my most effective in this role when the interventions are earlier, gentler and more private. Puncturing the self-importance of hierarchical organisations and self-interested people can be hugely gratifying but I’ve learned to my cost that in the long run it tends to be a less productive way of achieving things. Change achieved through consensus and gentleness tends to be more enduring than that which is forced on people, and audience matters hugely. While the requirement to call out the nakedness of the emperor is always there, much better for everyone to do it in private rather than during the parade if you can.

The Emperor and his New Clothes is the canonical example of the risks of not having that truth-teller in the room, before the decisions become public. The story is told as a parable about being clear-eyed and unafraid to speak an uncomfortable truth, but what really interests me is that the emperor has a court that has allowed him to be naked in public to avoid some small embarrassment for them. The bigger truth is about the court and the incentives and motivations within it rather than about the event itself. That moves beyond a moral in a children’s story to a commentary about the structural challenge: how do you highlight organisational shortcomings without inducing a defensive reaction from the people in power. The only thing worse to many senior people than being made to look foolish is being made to look “less than” in front of your boss. I’ve learned a huge amount about myself and how I deal with people through interactions like that, and from more than a few missteps which have resulted in banishments but thankfully nothing more permanent. And I have always been blessed to be in an organisation that understands the value of that questioning, challenging, voice.

Those who argue that the press, the court of public opinion, social media or the like now serve the same aim miss the importance of the jester’s role – the jester highlighted the absurdities and contradictions in the king’s thinking rather than criticising his decisions. That shaped the decision-making process itself and therefore produced better decisions. To do that you need to be in the room, with permission and access to the powerful, as decisions are being made. Criticism from outsiders after the event can be dismissed by the powerful in a way that gentle mockery during the process can’t be.

The need for honest, direct and open challenge that is in the organisational as opposed to personal interest is as strong as ever, but without a well-understood resolution like in medieval days. It’s a tightrope to walk, there is precious little thanks and it is a lonely place to be a lot of the time. To be truly useful in the role of the jester you need to accept that sometimes you will be told “not that much truth. Not said to that much power.” And you still come back for more, because if you aren’t bouncing back then you aren’t finding the limits.