When Enneagram Four leaders become transformational ones, they must move from Melancholy – the continuous thinking abut what’s missing, with the accompanying thoughts of being disconnected or separated from others – to Original Source. Original Source is the insight that then becomes the pervasive belief that nothing is missing and that everything and everyone is fundamentally deeply connected because we all emanate from the same source. Melancholy may not sound appealing, although from the Four perspective, it is the way the world is and melancholy can be sweet, allowing you to get in touch with a humanness that is a substitute for the truest form of connectivity.

For many Four leaders, moving away from melancholy seems to be a big challenge; they are wired for it, get both pain and pleasure from it, and how can they trust the belief that there is such a deep connectivity, they don’t seem to experience very often. And when they do, this connectivity seems so short or it ends so abruptly. To really believe in Original Source is a leap into what is already known, but seems so impermanent (yet, when in the high state, Fours know always there).

This was the dilemma for Brian, an Enneagram Four, a leader, and engineer by background, and a sensitive and capable human being. When he was the head of engineering for a large aerospace firm, he had thought he was doing well. All functions that reported to him were meeting their targets and well run, he had the respect of upper management, and he worked well with his peers. Then, Brian was taken by complete surprise. The organization has undertaken a 360-degree feedback initiative, surveying Brian’s bosses, peers and sampling those who reported to him. Although his bosses and peers gave him high reviews, this was not true for those who work for him. Both his direct reports (those who worked for him directly) and employees worked for managers who reported directly to him had issues with his management style. Not only was this the first Brian had heard this feedback, he was stunned by one common theme; they did not perceive Brian as supporting them in their work and, especially not supporting them with upper management.

Although Brian tried his best to resolve the above issues, he was deeply hurt, both that people had not come to him directly, but also because in his own view, he had supported everyone who worked for him, whether that person was a direct or indirect report. Bruised internally, he stayed in the organization for several more years, then worked in management for a medium-sized company, and finally became the head of engineering for a start-up organization where engineering was central to their line of business.

At Luminex (a pseudonym for the real company), he thrived (or so he thought) in his role, but then top management decided to embark on a 360-degree feedback effort and all the old feelings of hurt, betrayal, disbelief, anger, and sadness re-emerged. Based on his role, Brian could not stop the process, nor did he feel comfortable sharing his dismay and anxiety about this. For several months, he kept all this to himself, while staying active as a leader. When he received his one-on-one feedback, he was very nervous and the feedback was generally positive; his direct employees respected him as a leader, as did others in the organization that did not work for him. In terms of negative feedback, there were two key items: his direct and indirect reports mentioned that he told so many long stories so often that they felt this became tedious over time. They liked the stories, just not so many or so long. The second issue, the more serious issue, was that almost everyone in the organization, not just the engineers, thought that the organization was highly siloed – parts of the organization was sealed off from other parts, hindering communication, coordination and the sharing of resources – and this was especially the case with engineering.

Although one might think Brian would react very defensively to this information, he was actually overjoyed by the feedback. Tearful and choked-up, he explained that he had been so hurt and humiliated by the negative feedback years before (not being supportive of the engineers) that he had been overly protective of them in this new organization. For him to learn that he was highly respected by everyone within his engineering function as well as those who were not engineers was such a boost of appreciation that he was able to recognize that he was creating an engineering silo just to protect himself. More importantly, he easily recognized there was no longer a need to do so. As for his prolonged stories, that was no problem for him to correct.

This experience became Brian’s transformation as a leader. All the personal work he had done to deal with his feelings had paid off, and he no longer needed to protect himself. He was highly connected to everyone and didn’t even know it. Now he recognized what he had been too afraid to see, and for him, it was pure beauty.