This chapter considers the psychodynamics of groups and suggests that to make executives effective and create great workplaces, organizational leaders require a deep understanding of what happens when groups of people come together. Therefore, decoding the interactions between group members and how groups form, function, and dissolve, must take center stage when helping clients decipher the intricacies of organizational life. Drawing on Wilfred Bion, three basic assumptions made by those in a group setting are discussed. Dependency: in an organizational setting, people often assume unconsciously that organizational leaders should offer protection and guidance. Fight–flight: the organizational world is inherently dangerous. Pairing: pairing up with a person/subgroup perceived as powerful will enable one to cope with anxiety, alienation, loneliness. Additional defensive reactions are then discussed: social defense mechanisms (a group unconsciously colludes to protect itself against the anxiety/tension in the workplace) and “folie à deux” collusion (a “shared madness” between leader and follower that can turn into a mass organizational insanity). Yet, although the chapter concludes that change cannot occur without a modicum of madness, it warns that in our digital world discerning fact from fiction can be difficult, and this is where a clinical approach becomes ever more important.