My Leadership Worldview

Evan Crain
6 min readApr 6, 2024

I write this statement so that you may understand my hopes for what my hands produce from my work. In this paper, I will share my worldview and describe the consequences on how I work.

Archilochus wrote an obscure line about foxes and hedgehogs that an Oxford don turned into a career by postulating the meaning of the line. Something to the effect of “Foxes know many things but the hedgehog knows only one big thing.” Foxes are the tacticians and logisticians who make the world work — as in, most people in business. They see life as a series of means and approach a diverse problem set independently and shrewdly. Hedgehogs are the visionaries and entrepreneurs, who usher in change in how the world works. They see everything as connected toward an end and push aggressively. Most people are one or the other. The basis of grand strategy, according to John Lewis Gaddis, requires holding these opposing concepts at the same time to accomplish an improbable end using realistic and diverse means.

I tend naturally to be both a hedgehog and a fox — seeing complex relationships between all things but utilizing diverse and practical means to reach an end. My deepest discontent with work is when I am under the authority of people who deny me the opportunity to carefully act across dimensions — space, time, domains — to cultivate a better environment. My deepest content, then, is to build across these dimensions — what does that look like?

I’ve had a seemingly meandering path that has honed a natural talent for building amid complexity. I have lived on this country’s northern and southern borders and our east and west coasts. I even skipped across the pond to France for some time. After making my fortune in knowledge and experience, I returned to the country’s heartland that had captured my own heart because of the people — Indiana.

I’ve never been drawn to one field or domain but in fact all of them — often quite simultaneously because the excitement for me is in the relationships between domains. I consider complexity to be elegant — think of any elegant room, object, or person. The source of elegance is in the beauty of how independently simple components are curated and meshed into one cohesive movement. Reality is complex, multivariate, and requires methodical, non-linear, analytical, relational, creative, and simultaneous investigations. I enjoy embracing and adapting to this complexity.

Yet, to me, embracing and adapting to this complexity has a specific purpose. Since I was young, I’ve had a particular sense that there is joy in cultivating a better environment in which people succeed. Over time, I’ve come to understand specifically my life’s purpose is to build leaders such that people prosper, thrive, and experience joy in creating things and solving problems. More specifically, I define success as

1. The right people,

2. Doing the right things,

3. In the right way …

4. … and having fun doing it

The right people will have a set of skills, interact with others in a certain way (culture), and be a certain way (nature). The right things are activities that solve problems and satisfy customer needs. The right way to do this is in an environment where the path to solve problems is clear and improves over time. Finally, I believe God originally made life to be enjoyed. While the fall introduced problems that make life hard, we ought to redeem work such that it is also enjoyable — a work environment that doesn’t make work enjoyable is pointless. This is what I mean when I say an environment is better.

For this to happen requires an interwoven fabric of factors that must be just so — this activity is complex. You may recognize a common framework for business factors with many variants, each including something like strategy, structure, culture, and people. But there are certainly more factors that make a business successful: timing, relationships, space, context, and more! Great leaders must dedicate themselves to the holistic needs of people, otherwise the environment will fall short of its potential for flourishing. In the business world, the result of all these factors coming together harmoniously is financial productivity. There are many ways to produce financial productivity in the short term, but my objective is to cultivate a better environment that leads to sustainable financial success.

I have a consistent method of building amid complexity that allows me to hold loosely enough to the tension between aspirations and reality to produce predictable outcomes. This is through my leadership approach, drawing on my entrepreneurial spirit — which to me is to create solutions where none exist — and my natural thinking style which quickly learns, assesses, draws on relationships between ideas across domains, and applies connections and conclusions to the present situation. My approach looks inwardly to the organization first — the people within are the leaders of future success. People are endowed with gifts, are inherently valuable, and ought to live out a purpose. People should seek abundance, to be creative, and sanctification. I always see an opportunity to develop teams into solving bigger problems, rather than constraining myself to simply solve today’s problem. It is my role to unlock success by making it a joy to be creative and to solve problems together. Over the years, my method has repeated itself:

1. Build trust shoulder to shoulder and win over people through simple wins

2. Bring in the right people to the room to solve the right problems

3. Assess what matters to people and connect solving problems to the people to build energy

4. Develop structures that enable people’s best work and remove blockers that prevent it — jumping in to help

5. Build upon successes and improve structures that didn’t work so well

6. Repeat the cycle

Accordingly, creating the environment is equally dependent on me bringing in the right people who are gifted in beautiful ways to then make stuff happen, but in the right way for the right things. My approach is determined to achieve an ultimate objective, and my means are highly iterative, thoughtful, people-centric, boundary-spanning, timely, and varying in rhythm — sometimes slow as I wait for things to fall into place, sometimes fast as all has come together.

Rhythm, specifically, is ever more important to me. While I have found I naturally suspend emotion in moments of crisis and lead with a calm manner and thoughtful course of action, I also must be careful of my health. I easily become sick and my early years of throwing myself into a course of action is no longer sustainable. I’ve found it is better to think on a matter rather than maintain momentum for the sake of momentum. This impacts where, when, how often, and how much I work.

The type of environment I create is also centered on my values — what I believe, how I behave, what I seek to share. Culture is when people are oriented around a common way of working together. I think you’ll find the culture I will cultivate and grow looks a little like this:

Ideas I utilize my intelligence to understand and share what is best, good, and right

Mission I bring people together to solve problems

Teaching I share what I know with authority in the pursuit of excellence

Hospitality I make people feel welcome

Elegance I enjoy beauty and complexity in craft, environment, choices

Sincerity I say what I mean and mean what I say

Playful Joy Let’s create things together. It’s how I play. Let’s play.

I will ask myself during interviews “Can I make it better?” and “Is better constrained?” My cycle only needs to be repeated until the environment has reached its ceiling of potential. The most exciting and also constrained scenario for someone like me is when complexity is flummoxing the best efforts of the experts — where there is no charted path and it’s up to me to define it; once defined, I am no longer required. Alternatively, environments with opportunity — whether due to brokenness or immaturity — are excellent playgrounds for me.

You can learn more about my perspective on complexity through the following two resources: my grad school research into how people are the key to enabling innovation at scale with improved probability of success, and an explanation of logical methods which are critical to seeing and addressing complexity. So, how do I build amid complexity, holding in tension ends and means? To me, it’s simple — being the fox and the hedgehog means having an excellent team and the type of leadership that enables the team. Collectively, they become a movement that cultivates the complexity of the environment to produce success. Which comes first? Neither, each build up each other over time. It’s the leader I am and what I seek for the team.

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Evan Crain

Transforming *What Is* into *What Ought* | Organizational Leader | Passionate Teacher | Creative Thinker