The CEO as Steward of the Tree

Some friends and I were recently discussing the CEO job description, with each of us sharing what we do everyday. The CEO role is different from that of a Founder, and I approach my responsibilities as CEO by viewing myself as Steward of the Tree.

Over the years, we have nurtured a tiny seed of a company into a healthy little tree. Our tree helps all sorts of creatures live their lives: it offers shade for customers, fruit for owners, and branches on which employees can build their nests. The leaves that fall during autumn decompose and fertilize the forest floor of our community. Our seeds scatter in the wind, take root elsewhere in the forest, and begin their own journey toward tree-dom.

Our tree is still young, and has plenty more room to grow. My task as Steward of the Tree is to help it fulfill its potential – to grow to maturity so that it’s impact is amplified many times over what it is now.

I can make reckless decisions that stunt its growth or kill it. I might push it to grow at a rate that’s ultimately unhealthy, and would cause its branches to weaken or would jeopardize it’s strength by not giving its roots time enough to dig deeper into the soil. Or I might be negligent or lackadaisical, so that other trees reach up and block our sunshine, and then our little tree will wither.

When I’m being most effective, there’s not really anything that I must do. The tree is just fine without me tending to it for a few days. But there is always something I could be doing: whether it’s pruning a rogue branch, inspecting a fungus, or simply learning about how to help trees be healthier.

If there’s nothing in particular that I need to do on a given day, rather than feeling lost, useless, or guilty about it (which I’ve come to learn is a common feeling among CEOs), I should feel some pride: I have helped a seed grow to a strapping young tree that doesn’t need my immediate attention. If the tree needs my constant tending—if I am fighting back blights or urgently toting buckets of water during dry spells—then perhaps I am tending it in the wrong way. That’s probably a signal that I could be doing a better job as a steward.

A core responsibility of the steward is to provide. Provide comes from the Latin prōvidēre, with prō meaning “forward,” and vidēre meaning “to see.” To be a provider, one must literally see forward.

Our executive team recently finished The Hard Thing about Hard Things, and we spent a good bit of time on the one of the common themes in the book: the difference between “wartime” and “peacetime” CEOs. In growing our business through four years of a great economic apocalypse, every day certainly felt like battle, and I’m grateful to have shared that difficult journey with some incredibly talented and committed people.

Today, we may not feel so many immediate threats to our existence—we have enough recurring revenue, enough operating income, and enough cash on hand to withstand a great many blows—but insidious threats still loom. We are no longer battling to ensure that our tree survives until tomorrow or next month. Today, we battle to ensure that our tree is thriving years from now. The threats are less obvious and palpable (which makes some aspects of the steward’s job more challenging), but they’re still all around us. We must still combat our greatest enemy: complacency.

A handful of writings and people that have influenced my thinking about the CEO’s job:

The Man Who Planted Trees, Jean Giono

How Andreesen Horowitz evaluates CEOs, Ben Horowitz (this post was also in THTAHT)

What a CEO Does, Fred Wilson

I first came across the “CEO as Steward” analogy from one of our customers, Scott Barr of Southwest Exteriors, an accomplished remodeler in San Antonio.

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Courage vs Risk Tolerance

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I recently received a survey from Entrepreneurs Organization, asking me to indicate my level of agreement (from Strongly Disagree to Strongly Agree) with a number of statements about courage in business:

Courage is taking meaningful action deliberately after careful consideration of the risk involved.

Courage involves taking an action that is for the greater good, despite short-term adverse consequences.

Courage is the ability to seize opportunities, even when fearful of the future.

None of these statements quite nailed it for me. To me, courage is the strength one needs to make a moral decision in the face of adversity. I tell my children that courage is doing the right thing even when it scares you.

Investing in new products or services is risky, but not courageous. Expanding a sales and marketing team is risky but not courageous. Modifying pricing that seems to work just fine as-is is risky but not courageous. In business, we do lots of things to increase the prospect for greater future gain by sacrificing the certainty of significant near term stability. This is the essence of risk.

Courageous business actions include things that a leader deems to be the morally right thing to do, but that could jeopardize near- or long-term profits. Some actions that strike me as courageous:

  • Speaking openly about your values in the hopes of positively influencing your customers and employees, despite the risk of alienating those who don’t agree with you.
  • Trusting employees to do the right thing, knowing that that means some will occasionally abuse that trust or make mistakes.
  • Telling your employees, when you really need them to focus on executing, that you only have a few months of cash left.
  • Refusing to work with a customer or partner that could bring you game-changing income but requires that you compromise your values.

What are some of the most courageous business actions that you’ve come across?


What is an entrepreneur’s most important skill?

I read recently that an entrepreneur’s most important skill was his or her ability to execute. Upon reading that, I immediately thought of all the exceptional entrepreneurs I know who (if left alone) couldn’t execute their way out of a paper bag.

Those entrepreneurs have different skills that seem to serve them well. Their most important one may be their ability to surround themselves with and motivate a group of people who can execute.

I like how Martin Luther King, Jr. put it:

If you want to move people it has to be toward a vision that’s positive for them. One that taps important values, that gets them something they desire. And it has to be presented in a compelling way that people feel inspired to follow.