When Enneagram Two leaders become transformational leaders, they have to learn, often the hard way, that all the attention they give to support, guidance, listening, advice, and attention they give to others (all these are examples of Flattery) is really not transformational at all. Employees, peers, and bosses may like this behavior (or not), and they might even think the Two leader is quite evolved, but this is actually not the case. The perception that chronic attention to others is such a wonderful attribute can, in fact, reinforce the Two leader’s ego structure, the self-perception that he or she is such a good person and selfless leader, even better than the rest of us.

Perhaps what Two leaders need to understand is that undue, relentless, and habitual attention to others is their biggest obstacle to the spontaneous exercise of Free Will. Free Will, from the Enneagram perspective, is that ability to make conscious choices and take conscious action without the encumbrance of unnecessary constraints. In the case of Twos, Free Will means making conscious choices and being able to take conscious action without these choices being conditional on the “invisible audience,” the imagined or real reactions of others. For Twos, this involves acknowledging oneself fully and deeply – feelings, thoughts, needs, motivations – and the knowledge that only by doing this can the Two become autonomous, differentiated, and free. 

Such was the case with Monica, who at age 42 had risen up the ranks of human resources, starting in a support role and eventually becoming the VP of HR for a Fortune 500 company. Employees at all levels perceive her as accessible and extremely easy to talk to, and she is known for being responsive, timely, insightful, and highly empathetic. An excellent judge of talent in a wide variety of forms, Monica has always been perceived as a talent in her own right, but she actually prefers assisting others in the expression of their potential. All of this is very useful, but it does not make Monica a transformational leader; it simply makes her a very, very good leader within the confines of her ego structure.Here’s why…For Two leaders, supporting, assisting, and orchestrating situations on behalf of others is what they do naturally. What does not come naturally is being faced with doing what is really the best thing for the organization, especially if it is at odds with what people want. Similarly, holding to a strong position or opinion and being willing to voice it with inner strength and sustained power is an effort, and it is especially so when it is in direct contradiction to important people, such as those with greater power.

Monica’s personal transformation came when she recognized that she had a pattern of continuously leaving organizations in which she had felt an integral part, and the departure of them and pattern were always the same. The specific events that upset her were different, but the core theme was identical. After Monica’s having dedicated herself wholeheartedly to each organization for a period of years, advocating for people as individuals or groups, trying to change company policies and practices that to her did not feel humane, and/or having to implement a decision that she did not agree with, Monica would resign. Leading up to her resignation, Monica would become increasingly vocal in a critical way, she would then feel highly frustrated, and then she would ultimately quit out of deep anger. After many sleepless nights and just as many days of lethargy, Monica would follow her pattern; she would abruptly announce that she was leaving.

The problem for the organization was that Monica’s departure would always leave a big hole, both operationally and emotionally. Always, they were taken by surprise, although in retrospect, they could see the warning signs. There were many problems for Monica – for example, no job or income, a great deal of stress, remorse and residual anger. But the the biggest problem was that Monica ended up leaving the people in the organization she cared about the most. Even worse, she was acting out a repeating pattern that did not help her grow as a leader or as a person.

After repeating the above behavior in multiple organizations, Monica decided she either needed to choose another profession or stay in human resources yet alter her patterned responses. After some soul-searching, Monica decided to change her behavior, reasoning that no matter what profession she chose, her repetitive behavior would find a way to reappear. She simply, but not easily, worked on being less attached to all the people at work, feeling less responsible for the variety of outcomes that might befall them. She still cared, but not with the large investment she has previously felt. In a sense, Monica came to recognize that she needed a life of her own, a sense of self, and a feeling of well-being apart from being central to the lives of others at work.

As a result, Monica was able to take a new position as VP of HR, enjoy what she was able to do for people throughout the organization, yet not be so invested in the success or failure of her efforts that she despaired when she could not support the well-being of everyone at work. She became focused equally on her own well-being and the result surprised her. More people stepped up to taking responsibility for their own work lives, often citing Monica as a role model for how to do this. When she didn’t like a direction the organization was taking, instead of being emotionally charged when she challenged an initiative, Monica was now able to make a more balanced business case for her position. Often she was successful and sometimes not, but Monica had given up thinking she could or should be able to make every place she worked into the ideal workplace. Ironically, the less she tried, the more effective she became.