Coaching President Obama

I was recently asked to participate in a thought experiment: A friend was surveying theorists who work at the intersection of personality and leadership for a project loosely called “Coaching President Obama.” The question he asked was “How would you describe Obama through the lens of your personality model and what advice would you give him?” The challenge my friend ran into was the polarized views of the president, even among supposedly objective thinkers; many of the theorists surveyed either believed that the president walks on water and has no room for improvement or that he was completely inept and beyond help.
By way of disclosure, I voted for Obama twice and think he has been an average president; there are things about his governance philosophies and actions that I like and things I don’t. However, as an executive coach I always try to set aside any feelings I may have about a client and see them as objectively as possible. 
I also believe that Obama is a “Navigating Five” Ennea-type (i.e., a Social Five), or what I call “the Detached Navigator. I’ve written in detail before why I think Obama is an Ennea-type Five rather than, say, a Nine (as is commonly believed in Ennea-circles), and will simply reiterate that I see none of the typical Ennea-Type Nine derailers (particularly persistent self-deprecation and fuzzy communication patterns) and I see most of the derailers that I tend to see in the Fives I coach. I believe Obama’s cool demeanor and what seems like conflict avoidance (to those on the political left, at least) is often viewed as “Nine-ness” in the Enneagram community. While I see Obama as generally conflict-avoidant (a trait shared by Nines and Fives), I don’t necessarily see him as conflict-averse; in other words, he seems to avoid conflict because it seems illogical, not because he seems emotionally uncomfortable with it. In fact, he seems very comfortable taking a strong stance on topics that will alienate friend and foe alike.

Regardless, this exercise is highly speculative–I have not met Obama and am only speculating on his Ennea-type based on the evidence I see, and I quite doubt I will ever be asked to coach him:)–but it was an interesting exercise. Below is what I responded. Below that is my description of the Navigating Five subtype. PDFs of this and other subtypes are available upon request.
President Barack Obama seems to fit the personality profile I call “The Detached Navigator,” and I believe all of the strengths, vulnerabilities, and contradictions often seen in this profile are seen in the president.
The Detached Navigator has a deeply embedded need to focus on issues related to the group—mores, group dynamics, issues of justice, social hierarchies, matters of role and identity. At the same time, they strive to remain emotionally detached. They can take on a professorial air, and while they want to engage with others it tends to give the feel of a chess player moving pieces on a board rather than the visceral human contact of someone like Bill Clinton. In short, Detached Navigators are passionate about the group as a whole but ambivalent in their willingness to emotionally connect to the individuals within it.
People with this profile are prone to predictable blind spots and derailers. The most crippling blind spot can be their intellectual arrogance. They are often used to being the smartest person in the room and they may know that they come across with some intellectual arrogance, but they don’t realize how vividly others see this arrogance. One outcome of this blind spot is a paternalistic approach to leadership, an Ataturk-like attitude of “for the people, despite the people.” (To be clear, I would not put Ataturk in this same personality category; further, any speculation on President Obama is provisional since I have not interacted with him directly.) The Detached Navigator’s intellectual arrogance can make them overconfident in their opinions, and despite being generally data-driven they can dismiss data and the advice of experts when they become emotionally attached to their predetermined goal. They alienate others by making them feel stupid or uninformed.
There are some common derailers I see in executives of this style that I see in President Obama as well.
The first derailer is closely related to their intellectual arrogance: a tendency to need to show off their intellect. While they would rarely admit it, Detached Navigators enjoy a stage on which to show just how smart they are. It can come at the expense of others at times, and even if it doesn’t involve putting others down, no one responds well to a show-off who presents an implicit message of  I’m smart and you’re not.”
The second derailer is a failure to nurture critical relationships. They can be very good in environments that provide a safe distance from the audience (think of President Obama on the stage), but they seem to lose their vitality in smaller groups or unstructured situations (think of the president during a press conference). They avoid emotional entanglement, preferring to keep their interactions with those outside a very small circle distant and, for lack of a better word, theoretical. They may fail to truly appreciate that humans are emotion-driven creatures, and they may neglect the emotional needs of their audience and work partners. They seem attached to Plato’s allegory of the Charioteer—reason in charge and controlling the bridled passions—when, in fact, a Hume-ian view of emotions running the show and the intellect often serving to merely rationalize our emotion-based choices is more accurate. Thus, they think that they can rely on facts alone to persuade others rather than practicing the relationship building that makes others open to one’s facts and opinions.
A third derailer is not sharing information. It is common for this type of person to disappear and create a master plan by themselves or with a small group of advisors. They then unload this plan, in finished form, on others without having made key stakeholders feel included in the process. This lack of inclusion and consultation ensures resistance, no matter how brilliant the plan.
Were I coaching President Obama, I would focus first on the importance of building a more-personal relationship with those with whom he must collaborate. Intellectually, the president seems to understand this and capitalizes it on it masterfully in his campaigns. He seems sometimes to forget it when it is time to govern, however, and the oversight may be due to his overreliance on his adaptive strategy of striving to be detached. I would look at how that nonconscious habitual strategy impedes his ability to connect at more local levels and work on strategies to overcome those impediments. In short, we would focus on improving empathy in a very particular set of environments. The other issues—the intellectual arrogance and the tendency to not share information—would be addressed in the context of improving that empathy.

Description of the Navigating Five:

Overview: N5s navigate the social domain by striving to be detached. Like all Navigators, they are instinctively attuned to issues of hierarchy, identity, status, group mores, and interpersonal relationships. N5s approach these issues through a strategy of striving to be detached, trying to walk a fine line between detachment and engagement. They are intrigued by and drawn to the group, they want to participate in its activities, but they tend to intellectualize their involvement and take an advisory role. They are the big-picture, strategic thinkers who may appear to see the members of the group as chess pieces on the board and who are always thinking three steps ahead. They are often warm, funny, and quietly engaging, but can also seem to disappear and become remote. These conflicting needs—the instinctive need to connect and the strategic need to detach—results in others often infer contradictory signals from N5s, drawn to the warm side but confused by the emotional distancing when it occurs.
When viewed from the perspective of Enneagram wing theory, N5s often seem to have a both wings—the sometimes-introversion associated with a Four wing and the need for connection associated with the Six wing. Frequently, N5s are mistyped as Nines because they are interpersonally warmer and less willing to be publicly confrontational than other Fives.
At work: The biggest challenge N5s face is maintaining their enthusiasm while engaging in the day to day messiness of interacting with complex groups. They love puzzles to solve, whether those puzzles are technological, organizational, or strategic. They shine in advisory roles, and when given the time to sit back and reflect. It is easy to underestimate just how well N5s understand other people and how the group culture works. N5s often have a high power drive, meaning that they want to influence their environment and shape the culture, but they are conflicted in how public they should be while doing it. They frequently see themselves as important contributors to defining the strategy and culture of the organization but usually count on others to execute the strategy and shape the culture.
Leadership Style: N5s can make effective leaders in that they are often good at establishing and selling a vision, and they are also effective at the back-room strategic political maneuverings often required in leadership. Where they can struggle, however, is in the every day implementation of the strategy and the politics. They find the day in, day out massaging and nurturing of the group necessary for effective leadership to be tiring and unappealing.
Working with N5s: It is important to understand the dual nature of the N5s personality—to understand that they will tend to seem open and approachable one moment and remote the next—and to calibrate your expectations of them. Smart leaders are quick to use N5s as sounding boards and advisors, but also understand that just because the N5 understands what needs to happen and can get others excited about their vision does not necessarily mean that they will be effective at implementing it.

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