You Don’t Need to Be “That” CEO: Finding Your Leadership Edge With the Enneagram

In business, there’s this stereotype that a CEO has to be a table-thumping, stage-dominating executive—the kind of figure you’d see on the cover of Fortune 500 magazine. But if you look closely at the world’s most successful companies, you’ll find leaders of all stripes who built empires through a different kind of leadership. 

What do they have in common? They leaned into their natural wiring and turned it into a distinct leadership edge. Here’s what that means for each Enneagram type.

Enneagram One: Doing Things “Right”

Perfectionist type Ones lead through their commitment to doing things “the right way,” even when no one is looking. Steve Jobs, who many type as One, famously insisted that the circuit boards inside the original Macintosh computer be beautiful and neatly laid out. When his engineers argued that no one would open the case to see them, Jobs shot back with this: "A carpenter doesn’t use a piece of ugly plywood for the back of a cabinet, even though it’s against the wall... You’ll know it’s there, so you’re going to use a beautiful piece of wood." Such uncompromising standards redefined expectations for what technology should be, turning Apple products into icons and the brand into a cult. 

Of course, “perfection or bust” energy can have a messy underside. Jobs was known for publicly berating his teams and slamming ideas as “crap,” which earned him a reputation as a harsh manager. But for Ones who pair their high standards with patience and compassion for others, that same drive for excellence becomes a powerful force for building teams that consistently produce standout work.

Enneagram Two: Empathy as a Business Model

Type Twos are often dismissed as “too nice” for the C-suite. That may be true for the “move fast and break things” culture of Silicon Valley, but Twos excel as leaders in companies rooted in the well-being of people, whether it’s customers, employees or the world at large.

A great example is Jessica Alba, the founder of The Honest Company. As she explained in this interview, she started the business after she broke out in a rash from “baby-safe” detergent while pregnant and realized the industry was failing mothers. The company’s motto, “For us, it was never just about clean. It was about love,” reflects her commitment to prioritizing people over pure profit.  Twos who lean into this people-first instinct in a conscious way—by letting their care guide product decisions, hiring and how they show up with their teams—can create brands that customers trust and employees want to stick with.

Enneagram Three: Image and the Drive to Win

Threes are masters of the personal brand, and their leadership edge is the ability to relentlessly polish their image and sell it as a lifestyle. Kim Kardashian is the gold standard here. Even though critics shunned her as a leader, saying that her business success was based on “fame-leveraging” rather than leadership or innovation, the results say something entirely different. SKIMS, the shapewear and apparel brand Kardashian co-founded, is now valued at over $5 billion.

The Type Three edge isn't just charisma and polished image though. They have a fierce “get sh*t done” mentality and relentless work ethic. As Kardashian said in her viral Variety interview: “Get your f-ing ass up and work. It seems like nobody wants to work these days.”

Enneagram Four: The Courage to Show Up Authentically

A Four’s leadership edge is their courage to show up as their raw, unfiltered selves. For example, when the late Alexander McQueen was appointed as the Head Designer of Givenchy in 1996, he was expected to “refine” his image by adopting the posh mid-Atlantic accent common in high fashion. But as documented in McQueen’s biography Blood Beneath the Skin, he refused to change his thick Cockney accent and encouraged his inner circle (the London gang he brought with him) not to “polish” their personalities to fit the Parisian elite. 

Those who worked for McQueen described him as a leader who operated with intense emotional transparency. If he didn’t like a garment, he would rip it apart right in front of its creator. In the words of House of McQueen playwright Darrah Cloud, he was a man who “wore his heart on his sleeve.” This, in a nutshell, is the Four's leadership edge: a commitment to being real that was undoubtedly a key factor in McQueen’s fashion brand success. 

Enneagram Five: Systems Thinking

Type Fives are the typical “brains behind the scenes” leaders. Their natural edge lies in systems thinking—an ability to view complex issues as interconnected systems rather than isolated, individual parts. 

Elon Musk, a textbook Five, famously applied this to SpaceX. Rather than accepting the industry “truth” that rockets are—pardon the pun—astronomically expensive, he deconstructed the whole manufacturing process and calculated the raw market costs of aluminium, copper, and so on. This analysis showed that materials accounted for only 2% of a rocket’s price. So he decided to build the SpaceX rockets from the ground up rather than buying from middle-men and slashed costs by almost 90%.

Fives who lean into this edge break problems down to first principles and quietly rebuild processes to be more efficient. When they bring others into that thinking instead of hoarding it, their analysis becomes a powerful driver of change rather than just something impressive in their own heads.

Enneagram Six: Caution

Sixes are skeptics, and their leadership superpower is the ability to anticipate and manage every possible risk. Take Warren Buffett, the classic Six financial leader. His entire investment philosophy is rooted in identifying what he calls “moat”—companies with durable competitive advantage that makes them recession-proof. The CEO of Berkshire Hathaway also refuses to invest in things he doesn’t fully understand (he’s known for his hate for crypto and complex tech bubbles).

Complementing their carefulness, Sixes are reliable and trustworthy. Buffett’s annual letters to Berkshire shareholders are a great example because, in them, he talks more about what he did wrong than what he did right. It’s rare to see this level of transparency and humility in the corporate world, and it has helped him cultivate a shareholder base so loyal they’ve been dubbed “the cult of Berkshire.”

Enneagram Seven: Big-Picture Thinking

The leadership edge of Sevens mimics their approach to life in general—their belief that the world is a playground of infinite options. Richard Branson’s famous quote, "Business opportunities are like buses, there's always another one coming” perfectly encapsulates the abundance mindset that allowed him to launch over 400 companies under the Virgin umbrella. 

However, Sevens’ edge isn't just in seeing the next bus. It’s also in their refusal to get stuck riding the current one by getting bogged down in the nitty-gritty of daily operations. As Branson writes in The Virgin Way, one of a leader’s most important tasks is to find people to delegate the boring stuff to so that they can focus on expanding: “Early on in your career, find someone better than yourself to run the business on a day-to-day basis... Remove yourself, maybe even from the building, and from the nitty-gritty. That way, you're going to be able to see the bigger picture and think of new areas to go into.”

Sevens who use this edge well stay close to the big picture while making sure someone they trust is steering the details. A good team can turn their constant stream of ideas into new products, projects and markets instead of just living in their heads.

Enneagram Eight: The Courage to Challenge the Status Quo

Eights don’t just lead in the sense of directing and managing projects or people. They attempt to overthrow the status quo entirely, aiming to replace rigged systems with a new order built on fairness and transparency. 

Mark Cuban’s latest venture, Cost Plus Drugs, is a quintessential example of Eight’s leadership edge in action. His pharmaceutical wholesaler business is disrupting the entire industry by removing the middlemen—like pharmacy benefit managers who profit from opaque pricing—in order to protect the “little guy” (the consumer) from being price-gouged.

Another defining aspect of the Eight’s leadership edge is their confrontational, no-BS attitude. Cuban illustrates this perfectly in Shark Tank when he bluntly calls out bad business ideas. For Eights leaning into this edge, the promise is a high-velocity culture where people don’t waste time on bullsh*t (like meetings, which Cuban famously hates) and work just gets done.

Enneagram Nine: The Gift For Harmony

With their natural gift for harmony, Nines find their leadership edge in their ability to unite conflicting parties. When Satya Nadella took over as CEO of Microsoft in 2014, the culture was so fractured that it was satirized in a viral cartoon, which depicted Microsoft’s departments as silos pointing guns at each other in a “Mexican standoff.” 

When Nadella came on board, he pivoted from that friction-heavy culture of the Steve Ballmer era (unhealthy Type Eight energy) toward one focused on empathy and connection. As Nadella writes in his book Hit Refresh, he did that by leaning into his Nine edge. In practice, that meant listening (through surveys and one-to-one meetings) and bringing people closer to one another by placing them in contexts where they could learn new things together. 

What Can We Learn From This?

The “Fortune 500” CEO represents only one type of leadership. Thinking that all leaders must be cut from the same cloth is a myth that limits your potential. Everyone can be a leader—it's just about finding a place where your natural leadership edge shines. As these real-world examples show, the most effective leaders don't waste time obsessing over the traits they lack. They lean in to their personality type’s natural edge, and the Enneagram can help you identify yours.