The Enneagram’s true purpose

I’ve taken the Myers Briggs, the DISC, the Kolbe, a proprietary test that my executive coach administered, and probably a couple other assessments along the way that I’m forgetting. Usually they come up in the context of business, with utility like constructing a complementary team, or understanding your coworkers, but in all of them I always end up in the same spot: “Interesting. Now I guess I’ll go back to living my life.”

The Enneagram has been much more useful.

The original thoughts behind the Enneagram are either from ancient Egypt, or 4th century Alexandria, predating all the other assessments by quite a bit. Nothing lasts that long without having something of import to it (if the DISC is around in the year 4,500, we can revisit this).

Nevertheless, when I originally heard about it I lumped it into the same category as the other assessments, another way to categorize people that is neither more or less accurate than any other. And in a sense, honestly, it is exactly that. But where it differs, and becomes much more than a simple bucketing exercise, is in how it’s intended to be used.

From the Enneagam Institute:

One of the most profound ways of understanding the Levels is as a measure of our capacity to be present. The more we move down the Levels, the more identified we are with our ego and its increasingly negative and restrictive patterns. Our personality becomes more defensive, reactive, and automatic.

The movement up the levels is simultaneous with being more present and awake in our minds, hearts and bodies. As we become more present we see our personality objectively in action rather than “falling asleep” to our automatic personality patterns. There is therefore the possibility of “not doing” our personality.

I’ve found that the best leaders, and myself when I’m at my best, are those people who are fully invested in the person they’re leading. The more present the person, the better the leader. For that, but not only that, reason, I’ve spent considerable time and effort rewiring my brain to focus on being ever more conscious in and to the moment.

Beyond leadership, this is also my understanding of the Path that is in some way referred to by nearly all the wisdom traditions (Buddhism, Hinduism, Advaita Vedanta, Christian Mysticism, Kabbalah, Taoism etc), as well as plenty of secular thinkers (Sam Harris, Brene Brown, etc). Even Lululemon bags note that “living in the moment may be the meaning of life,” although that probably only proves I’m subject to marketing.

Either way, as a longtime “intellectually superior atheist” this wasn’t the path I’d expected to go down. If the me of today were to meet the me of any age between 17-33, I’m sure I would have laughed at myself. Or

But then again, viewing that conversation through the handy lens of the Enneagram, that would have been a level-6 laughing up at a level-2, from deep in the clutches of his automatic and defensive personality patterns.

I’m good with that. The 17-33 year old me wasn’t near as effective a leader.

When to stop “crushing it”

I’ve been “crushing it” for almost as long as I’ve been running a startup.

That’s not to say that things have always been up-and-to-the-right. We’ve had more than our share of WFIO moments along the way. But to most anyone I spoke with, we have always been crushing. I made sure of it.

I have always kept the key metrics by which we actually were crushing it at the ready at all times, because you never know who you’ll talk to and you need to be on your game when opportunity knocks.

There’s tremendous value to this. I have literally been in an elevator with an investor of limitless resources, and needed to position my company in the best possible light in less than 30 seconds to pique his interest enough to take an actual meeting with me. If I didn’t have that highly packaged version of our story at the ready, I legitimately would not have closed that round of financing. I certainly don’t mean to diminish the importance of presentation, as it’s critical to startup success.

That said, it’s worth knowing when to turn it off, too. And doing so can counterintuitively be a path to success.

If you’re always “crushing it,” you risk sugarcoating real problems that need attention, and prevent the outside perspectives that may actually help solve those problems from having a clear way to engage. In “crushing it” you present the image of success, but you may unwittingly do so at the cost of real, actual success.

Startups are hard. Over time we’ve cycled through periods of legitimately crushing it, and periods where I didn’t think we would make it. That up and down ride is the nature of the game, and the secret is that EVERY startup hits highs and lows, even though most don’t talk about the lows.

That’s for good reason. Talking about the lows will never get you funded. But on the other hand, “crushing it” communicates that you don’t need any help.

And sometimes we all do.

The (not so) new leadership: Context > Control

Many leaders still see their job as directing the activity of the people working for them, setting up detailed systems designed to remove the variability from human behavior and achieve predictable outcomes.

This approach to management stems all the way back to 1911, when Frederick Winslow Taylor released his opus, Principles of Scientific Management. His techniques were responsible for dramatically increasing the output of industrial era factories by limiting the freedom of employees to make decisions, instead creating detailed scripts to drive very specific, management-prescribed, behaviors. By creating a system that forced every employee to conform to standards in every situation, Taylor ensured maximum compliance, which at that time equaled productivity.

But that was a different time, and those employees were doing repetitive tasks in a factory. Today’s workers are asked to navigate rapidly changing markets and produce results in all kinds of situations, so compliance, at best, comes with many caveats. But many managers still use those techniques today. You see the issue.

Today, the most successful companies adopt a context > control philosophy to management. At VNN, it looks something like this:

  • Leadership’s job is to create context
    • Establish long-term vision, short term milestones needed to move toward that vision, and set any hard guidelines outside of which employees may not go (the goal is to make these as broad as possible)
    • From there, avoid making decisions wherever possible
    • Instead, ensure that everyone within the organization has the appropriate context to make their own decisions. Ensure everyone is aligned to where the organization is going, and understands their role in achieving the vision.
    • Then align some more (HT Patrick Lencioni).
  • Individual employees’ job is to use good judgement
    • Each employee is empowered to make the best decision for every situation in which they find themselves, based on the context provided by leadership

This way, the people closest to the situation, the ones best equipped with the most information about the situation–namely the employees–are the ones making most of the decisions. Meanwhile, leadership spends most of their time answering questions, providing feedback, coaching, training and generally ensuring that the decision makers (employees) have the context needed to make decisions in the moment that are aligned with overall company priorities.

Doing this admittedly requires humility on behalf of the leadership, as they need to embrace the fact that they cannot keep up with the pace of business on their own, and empower their team to help them make critical decisions (and then support them when they decide things different than you would). But I’ve found that if you empower your team, and expect them to step up, they do.

When they do, the rewards are many. In addition to better serving customers (by ensuring the person they’re talking to is empowered to help them without checking with their boss), this approach has proven to lead to a more engaged and productive employee base, and a greater level of innovation throughout the organization.

I remember the moment when I realized we had implemented this effectively at VNN: I had given feedback to an employee that I didn’t think a project he was passionate about would work, but I also let him know that, as always, my opinion was context and it was his decision, within the parameters we had constructed. He decided to go forward with it, busted his ass on the project around his core responsibilities, and it’s now one of our most successful business lines. I had to eat some humble pie on that one, but there’s no question that VNN would be less successful if I had dictated that particular decision.

What was a radical philosophy as recently as a few years ago, what I’ll call “context > control,” is quickly becoming mainstream. It’s not there yet, but organizations like The Ready, Whole Foods and Google are all leading the way, and VNN is working every day to do the same.

Many leaders still want to control every aspect of their organization. But the companies that let go of that control, democratizing decision making and embracing the full capabilities of their employees, will outpace those who centralize decision making and look to control results.

They already are.


In a future post I’ll detail exactly how we went about implementing this approach at VNN, and the structures we use today to ensure everyone has the appropriate context to UGJ (Use Good Judgement, which we stole from Netflix like any good artist).


It’s also worth noting that the above is nowhere near the leading edge of management. Recognizing the futility of pretending to control the future, some companies have gone so far as to eliminate the annual budget entirely. We still have a budget, but I must say this is very intriguing.

We live in echo chambers

I’m so right. All the time, I’m always right.

When I log onto Facebook I see it. Everyone is posting about politics, and every post berates the bad guys and glorifies us. My party. Everyone is saying the same thing: that I’m right. Those guys are bad, but we’re good. “What’s wrong with the world,” I’ll say before logging off.

Sometimes I enter into a business meeting with an agenda. Not the kind that helps to run an efficient meeting, but the kind where I intend to convince my teammates to do what I want. In these cases, I don’t bother listening, because I already know the answer coming in. And I make sure to ask the head of R&D his opinion, because I know he understands. If someone disagrees it’s because they’re wrong, so I just need to explain myself better. Eventually we go the right way. Or sometimes we don’t, but everyone makes mistakes.

In traffic, I’ve been told I’m the worst, but secretly I don’t believe it because I drive well. Some people, on the other hand, they zoom past you, then swerve into the front of the line of cars in which you’re waiting. That’s the worst. Immediately I get hot with fury, because I have somewhere to be. The selfish jerk.

I’m right at every level of my life, and every area of my life is all about me.

This morning I was late to a meeting so I had to cut into a line of traffic. Luckily there was a space between the cars so the guy behind me couldn’t have been too put out. It was unfortunate, but necessary. I waved at him..

I settled into the front of the line, and for just a moment, it seemed like something might change.

But then I quick pulled up my phone and checked Facebook, and the world looked Right again.

A love letter to Reboot, by Jerry Colonna

I’m not the type to read business books past the third chapter. I’ve found that pretty much all business books get to their point pretty quickly, and then repeat that point, approaching it from infinite angles, for the next 200 pages. It’s exhausting.

There are exceptions, however. And one business book changed my life.

Reboot, by Jerry Colonna, was released in 2019. I picked up the book because Jerry was hailed as “the CEO whisperer”, and one of the top Executive Coaches in the country, which I figured was right up my alley. But then the entire book was the opposite of what I expected in the best possible way.

Through an examination of his life story, interspersed with multidisciplinary perspectives from some of the best thinkers, both contemporary and throughout history, Jerry hits directly at the human side of starting and running a business, which to that point in my life was still pretty well unexamined. He addresses the toll that the specific set of circumstances in which founders put themselves takes on them as human beings. He does this in a way that hit me hard–his perpetual chasing of “lemon drops” as a proxy for feeling whole, for example, which is a feeling to which my entire soul can relate (although lemon drops themselves are meh).

Jerry also cites his sources in many cases, from Jung to Plotkin to Buddha, all experts with various perspectives on the human condition (all “different fingers pointing at the same moon”). I cannot express my gratitude for this choice enough, as it enabled me to go on a months-long, on-and-offline google-deep-dive into the ancient wisdom of how to be a human being, a dive that continues to this day and is responsible for my budding faith (if you can call it that, I’ve been an athiest most of my life so I’m still not sure that’s the right word).

The core hypothesis driving all this–which to be fair he stated in the first three chapters so I could have stopped there, but I’m so glad I didn’t–was that better humans make better leaders. The book, therefore, along with his coaching company of the same name, is intended to help leaders become whole in their humanity, thereby enabling them to lead other humans to become better versions of themselves. It’s a brave approach amongst so many books offering ways to push your humanity ever deeper in the quest for ultimate achievement. I believe it’s also a necessary approach, as there’s no way I would have picked up a book about ancient wisdom and feelings unless it was smuggled in under the guise of productivity, such was my blindness. Jerry Miyagi’d me.

In the guise of a business book, Jerry penned a letter on how to live a life, written specifically for those of us who have already made the decision to prioritize our business over ourselves. It’s full of necessary information for founders which is hard to find elsewhere. Wrapped in a package of productivity, Jerry smuggled in one of the three most profound transformations of my life.

Wax on, my friend.

Sales teams are more than that

I heard a story once that stuck with me, about the nature of experience.

A small girl walks through a garden for the first time. In the garden are green things of all kinds, which she has never seen before. She is overwhelmed by the scents, the colors, the sheer magnitude of the experience. She spins, feeling the sensations in her outstretched arms as they brush against the various plants. She has not felt more alive than at that moment.

She runs back into the house to tell her mom about her experience. Her mom says “I saw you running about in the flowers. Those are pretty, aren’t they?”

She goes back into the garden the next day, and smiles at the “pretty flowers.”

We label things with concepts and words out of necessity–it’d be impossible to navigate the world if we didn’t know the concept of food or shelter–but the labeling creates a distance between us and the garden, such that we don’t see the garden in its entire complexity and majesty any longer, instead seeing it as simply “garden.” The label strips away the nuance and flattens something that is inherently three-dimensional and five-sensual to a mental concept. It turns the profound experience of Life into an idea that can be filed away along with millions of others. Nothing special.

I see myself doing the same thing in business. With a simple label, a complex group of wonderful and mysterious people, with tremendous, multifaceted value to add to the organization, become simply a “sales team”, or an “engineering team.” And thusly, I limit their contribution to merely that.

It’s not wrong to abstract the world this way. Again, it’s necessary. But every once in a while I’ll find myself in the woods or on top of a cliff and experience that rush of Existence once more, and in those moments I’m reminded that that’s our default state. That wordless, free place is reality, not the endless list of concepts we shuffle and categorize to make sense of things. The words “cliff” and “forest” and “engineering team” are useful, but they’re an inadequate substitute for the real thing.

I am doing my utmost to remember this, both in business and in life.

One of the most important lessons I’ve learned in business

I never went to business school. My business education was a startup accelerator called Momentum.

Patterned after TechStars, Momentum gave entrepreneurs a $20,000 investment and placed them in a 12-week bootcamp, which was intended as a crash course in everything needed to start a tech business and raise venture capital. As a part of that bootcamp, every Thursday night all the entrepreneurs would gather around for a “fireside chat”, where we would have the opportunity to listen to a business leader tell their story. Out of 12 of those chats, one moment sticks with me to this day.

We’ll call the business leader Bob, although that’s not his real name. Bob was the type of guy who flies a helicopter to work, and so obviously had a different perspective on life and business than I had. Bob was incredibly successful, but also went out of his way to be accessible in that conversation, which I really appreciated.

Someone asked him: “If there was one lesson you’d hope that these entrepreneurs would learn in starting their businesses, what would it be?”

Bob thought about it for a moment. He took a beat longer than normal as, we had learned that evening, was his way.

“I’ve worked with companies all over the spectrum,” he said at last. “From Fortune 100 companies to pro sports teams to two-person startups. And across all those companies, there’s only one thing that all of them have in common.

“Nobody knows what the hell they’re doing,” he said.

“The difference between successful companies and unsuccessful companies, is that with the successful companies you can’t tell.”

Which type of team are you? Football or basketball?

A football team consists of 54 specialists, each with a finely tuned set of skills and an equally specific role, ready to be called upon to perform their function to the most specific degree possible. It is coached from above, with detailed schematics and complicated formations, and the best players are determined by who can perform their role with the most exactitude. Quarterbacks execute a decision tree of reads, wide receivers run precise routes, kickers kick. It enables a large group of people to coordinate with precision, and when executed well (Patriots’ “Do Your Job” mantra) it enables a level of complication and replicability in strategy that can be very effective.

A basketball team consists of 12 generalists with complementary sets of skills. Each player has a specific role (most of the time, although trending less so), but is expected to make good decisions based on analyzing a rapidly changing and complex set of circumstances in the moment, and best applying their skills to the situation. It is coached through a combination of general skill development and strategic philosophy, the latter of which creates a default framework within which players can either execute or deviate at their discretion. So point guards run the offense, mostly, except when it’s advantageous for a forward to initiate. And centers rebound, except when the guard is closest to the ball, in which case he does. The best players are the ones who deliver results, regardless of their adherence to the offense, but the best teams are those who work as a single unit, supporting one another’s weaknesses as needed.

Leading teams in business can be done either way, but it’s really important to distinguish which approach you’re going for.

Do Less, Better

Inspiration sparks the best ideas, creative process crystalizes them, and perspiration makes them come to life. Three parts of the value creation chain.

We startup founders are excellent at the perspiration part. We push and push, optimizing for a constant state of busyness, checking off more boxes than we did yesterday. Eliminating more gaps in our schedules in favor of “GSD” (getting shit done).

In doing so, we feel productive. We’ve been conditioned to “do more, faster“. And that’s not wrong, but the question is at what cost?

Inspiration and creativity require one thing: Space. The very thing that our quest for productivity would have us eliminate. We’ve been sold a line that we must hustle ad infinitum, and bought it wholesale with little awareness of the implications.

Nothing happens without perspiration. It is the core characteristic of successful founders, and foundational. But successful founders get that part, and then go too far.

With the way we glorify the hustle as founders and leaders, is it really a surprise that true inspiration and creativity have become so rare? Why everyone is just the “AirBnb for pet crates” or the “Uber for luggage”?

Scaling value while also scaling variability

Scaling a business, we’re told, is about establishing processes, procedures and workflows, to ensure that the value that you created when you were small persists as you grow. The goal being to ensure that every experience your new customers have is of the same value as the experiences your early customers had. To do so, it seems, you have to eliminate variability to prevent substandard customer experiences.

But variability drives innovation. Without random variation, single celled organisms never evolve into human beings, and nobody even has the luxury of thinking about scale. Variability is the singular engine driving adaptation, growth, and increasingly, in the rapidly changing world we live in, survival.

So can we scale both value and variability? Should we?

You simply can’t replicate the chaos that permeates an early stage startup as a company grows, and you shouldn’t want to. We all have enough grey hairs from that time. But if we convince ourselves that there is a “right way”, then our teams will hew ever closer to that. Then, innovation stops, people get caught up in dogma, and the company struggles to meet evolving expectations in a dynamic market.

Even though everyone in the company is doing everything “right.”

What if we aimed instead to scale not only the value creation that we cultivated at a small size, but also the variability that helped us find that value creation in the first place?

As an example, what if instead of a “right way”, we instead scaled a “default way” for our teams (HT: Aaron Dignan), while also giving them autonomy to deviate if it made sense? If we did this, our teams could do what had been proven effective in the past, but they could also change things if they thought it was for the better. They might be wrong, or they might be right, but either way the organization would be smarter having conducted the experiment.

Might we be able, this way, to scale customer experiences better than the ones we first had success with?