Leaders have power and influence. Without any form of counterforce, leaders may become unaware of their imperfections. Mistakes made by the leader can have serious consequences for the entire organisation, or any other context. To avoid such consequences, it is important that there is someone who helps the leaders reflect on their behaviour. Nowadays there is a diversity of checks and balances trying to keep the leader on the right path, trying to prevent negative consequences. However, from a historical perspective, there used to be a profession that is lacking in the current corporate system and culture: the court jester. The court jester used to be the only one who could tell the leader, or in more medieval times, the plain truth. In fact, the court jester served 16 functions that might still be needed in current organizations. This research investigates how theses 16 roles of the court jester are embedded in the current system and culture of corporate governance In addition, the question that is raised is on whether all those roles could again be performed by one person and if so, how you can get this organizationally embedded.