How the Enneagram can improve communication and reduce conflict in family-owned businesses

The Enneagram is my favorite tool to understand an individual and family system. In the crowded-to-bursting assessment space, the Enneagram stands alone for its ability to create paths to transformation. Nowhere is this gift more vital than in family businesses, where years of history keep even the most competent adults stuck in the pettiest version of their 12-year-old selves – at work, no less. Brothers Darius and Reggie (fictional characters who represent an amalgam of my actual clients) are CEO and CFO, respectively, of a family business, and sometimes, their boardroom squabbles sound more like childhood bedroom battles. The Enneagram allows them to take a fresh look at their conflict using the hallmark “what, so what and now what” approach.

The what 

At its simplest, the Enneagram is a questionnaire that identifies people as one of nine core types, numbers 1-9. Each type has core motivations and typical behaviors. As an Enneagram Type 2, for example, I am the “Considerate Helper”, motivated by a need for love and acceptance. As such, I’m likely to offer help (whether or not the recipient wants it!) and have a deep-seeded need to be included. These motivations show up in a myriad of ways, some that serve me well and some less so. For example, being a 2 means that my profession, executive coaching, comes naturally to me. On the flip side, I am a lifelong FOMO (fear of missing out) sufferer. Each core type has its own gifts and challenges.

I often begin a family engagement asking family members to re-introduce themselves through the lens of their individual Enneagram types. This simple exercise often yields entirely new insights into lifelong relationships. Let’s take the example of Reggie and Darius. Reggie is CFO of his family’s business and an Enneagram 6. His core motivation is safety. He therefore considers risks associated with business decisions carefully – and often for a long time. His brother, Darius, the CEO, is a type 7 and motivated by avoiding discomfort. Darius is extroverted with a high risk tolerance, constantly pursuing new ideas with little consideration, and abandoning them equally quickly. 

As a little boy, Darius, often surrounded by a small army of friends, would tease the more introverted Reggie mercilessly for being quiet, shy and cautious. The stoic Reggie rarely lost his temper at his dramatic older brother, but when he did, he dressed Darius down for being irresponsible and causing their parents pain. The brothers’ boardroom dynamics were hardly different. Darius would regularly float numerous ideas with no prioritization. Reggie would analyze each diligently and surface all possible risks. A frustrated Darius would decide that rather than engage with Reggie’s laborious risk assessments, he would go find more great ideas for the company to pursue – and the cycle would repeat itself in a painful, endless loop.

Each brother takes the Enneagram and is surprised by its accuracy. After digesting the results, Reggie and Darius meet separately with their coach to understand their results and identify how insights showed up for them personally and professionally. Their next step is for each to create a brief summary to present to his brother. Each fear that the results are so obvious that the exercise will be worthless, but their coach convinces them to give the process a chance.

The so what

The brothers meet with their coach and re-introduce themselves to each other by sharing a summary of their individual Enneagram results. The coach is delighted to hear the brothers laugh as each identifies some of his own annoying behaviors. At this moment, neither brother is triggered by any conflict, so the environment is one of high psychological safety for both, and light bulbs go off as each begins to interpret the “so what” of their respective types for his brother. Reggie explains to Darius that his core motivation is safety, and he loses sleep worrying about making a financial choice that might hurt the company. He is keenly aware that their widowed mother depends on distributions for her livelihood, so he views himself not only as a son, but also as a provider. Reggie acknowledges that this care guides every decision he makes and sometimes paralyzes him to the point that he procrastinates key decisions.

Darius, in turn, reveals that his core fear is pain and discomfort, and as such he has a “shiny object” problem. To him, every new idea offers the glittery appeal of faster growth and greater profit. Like Reggie, Darius also feels a strong sense of caretaking duty to their mother. He subscribes to the “throw spaghetti at the wall and something will stick” approach – create lots of options to distribute risk, and something will work out. Analysis paralysis is the worst possible outcome in creating safety for the family and, especially, their mother.

In the simple process of revealing core types and motivations, Darius and Reggie gain three significant insights:

  1. Their core motivations differ dramatically, so their lifelong conflicts around risk make sense.
  2. Their differences are actually complementary. If Reggie acts too slowly because he is mired in risk analysis and Darius acts too fast because he is maniacally creating options, combining both their approaches is likely to yield a “middle of the road” approach.
  3. They both feel responsibility for the business to succeed to support their widowed mother – in fact, both cite this care as their primary driver. 

These realizations quickly shift years of conflict into revelations of where the brothers are similar and different. The power of the Enneagram to effect such change, simply by providing common language for discussion of motivations and drivers, is enormous.

The now what

By now, Darius and Reggie have re-introduced themselves to each other using the common language of the Enneagram. They now see each other with new eyes, and understand that at heart, they both love Mom and want to take care of her. They simply approach that responsibility from different, yet complementary, perspectives.

Bolstered with this new insight, the brothers can decide what’s next. After a two-hour session with their coach, they decide to implement the following path to joint decision-making at their company:

  1. Once a week, they will meet to discuss key decisions they face. Reggie commits to meeting deadlines in preparing for that meeting, and Darius commits to not texting his brother 14 times a day with new ideas. Instead, they will create a shared agenda in Google Docs and add to it over the course of the week.
  2. They will start each meeting spending two minutes reviewing their Enneagram core motivations and needs.
  3. They will commit to framing recommendations with their core motivations in mind. Specifically, Darius will prioritize his many ideas and discipline himself to consider what could go wrong, and Reggie will force himself to consider what could go right.

No assessment is a silver bullet for harmony, especially in a family-owned business. At the same time, the Enneagram yields insights that help collaborate with people wired differently from you. We cannot change the past – Darius’s and Reggie’s boyhood fights are forever imprinted in their individual and collective memories, but those conflicts are also not life sentences. Using the Enneagram, Darius and Reggie are able to recalibrate their working relationship for the benefit of their company and, most importantly, to support their beloved mother.

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