Dec 30, 2022 9 min read

General McChrystal on Leading like a Gardener, not a Chess Master

How do you view your role of lead or manager? Is it as a chess master or a gardener?

The lure of control

Often unknowingly, leaders and managers suffer from the myopia of control. The underlying ethos is of knowing everything, solving problems directly and having everything under control. It's what helped them rise quickly through the ranks. But beyond a certain scale and level in the organization this tendency increasingly becomes a liability.

Four star general Stanley McChrystal puts it this way [2]:

I think up through probably 35, I was very much a control freak, because the size of the organizations I commanded, and I was part of, were small enough where I could micromanage them. I had a fairly forceful personality, and if you worked hard and studied hard, you could just about move all the chess pieces, no problem.

Around age 35 to 40, as you get up to battalion level, which is about 600 people, suddenly, you’re going to have to lead it a different way, and what you’re really going to have to do is develop people. The advice I’d give to anyone young is it’s really about developing people who are going to do the work. Unless you are going to go do the task yourself, then the development time you spend on the people who are going to do that task, ... every minute you spend on that is leveraged, is exponential return.

This dynamic is relevant not just to generals, but also to someone moving up from an individual contributor role to being responsible for a team.

The leader as the puppet master

Heroic leaders who appear to have it all figured out, and who dictate strategic direction from up above is still the default expectation. This is exacerbated by media and the leadership industry that exaggerate this notion. It's much easier to sell the "all-knowing" leader, and equally hard to sell someone who's enabling it and not always in the limelight.

But these notions are antiquated, and sub-optimal for complex, ambiguous conditions that leaders face in the hyper-connected, fast evolving world of modern organizations.

In Team of Teams, McChrystal highlights this flaw:

We gravitate toward “heroic leaders” who combine qualities we associate with leadership, such as wisdom and physical courage. For a generation after his 1815 triumph over Napoleon at the Battle of Waterloo, Arthur Wellesley, the Duke of Wellington, embodied this concept. Images of Wellington on horseback, deftly maneuvering troops, established an ideal: the leader as all-knowing puppet master, crafting brilliant strategies and distributing precise commands.

We've been conditioned to think about leaders in this manner. It's convenient because the lines are well defined and clear as to who's doing what – the leader leads while the followers follow.

But for modern organizations that face constantly changing situations on the front lines, this model is ill-suited for adapting optimally. It relies too much on the leader and thus is limited by their brilliance or folly.

The organization as a rigidly reductionist mechanical beast is an endangered species. The speed and interconnected nature of the new world in which we function have rendered it too stupid and slow to survive the onslaught of predators. In some cases, it simply lumbers into tar pits, lacks the strength to free itself, and slowly dies.

The traditional heroic leader may not be far behind. Yet even in our new environment, we still retain high, often unrealistic, expectations of leaders. We publicly demand high-level strategic vision and an unerring ability to anticipate broad market trends, but we simultaneously celebrate CEOs for encyclopedic mastery of every aspect of their business. We routinely ask government leaders if they knew the smallest details of an issue, and if not, why they didn’t. We expect our leaders to know everything, knowing full well that the limits of technology and the human brain won’t allow it.

The leader as the chess master

Another modern day malady that ails leaders is ready access to data, which gives the false impression of being in the know and thus wanting to control everything. The mistake is to think that more "data" and deft analysis will solve the challenges.

This notion is akin to chess — the leader as the chess master constantly watching for threats and opportunities on the board, while his strategic pieces are ready to move at his command.

But this is more a mirage and less a reality. Neither is it practical to expect leaders to "process" this vast amount of incoming "data".

Armed with unprecedented amounts of data, CEOs, politicians, and bureaucrats can peer into what is happening almost as it occurs. ... this information can seduce leaders into thinking that they understand and can predict complex situations—that they can see what will happen. But the speed and interdependence of our current environment means that what we cannot know has grown even faster than what we can.

McChrystal highlights how the evolving situation in Iraq in 2004 was too complex for the leader as chess master model to hold up. The enemy in this case was playing to a different rulebook, or in fact no rules.

...the chess metaphor quickly broke down. Even in its most rapid form, chess is still a rigidly iterative game, alternating moves between opponents. War in 2004 followed no such protocol. The enemy could move multiple pieces simultaneously or pummel us in quick succession, without waiting respectfully for our next move.

They did so with such speed that it was soon apparent that their changes were not the outcome of deliberate decision making by seniors in the hierarchy; they were organic reactions by forces on the ground. Their strategy was likely unintentional, but they had leveraged the new environment with exquisite success.

...Our teams were crafted to be chess pieces with well-honed, predictable capabilities. Our leaders, including me, had been trained as chess masters, and we hoped to display the talent and skill of masters. We felt responsible, and harbored a corresponding need to be in control, but as we were learning, we actually needed to let go.

The leader as gardener

So what is a leader to do if not to figure out what's going on and give commands? The answer is counter intuitive and does not come naturally to most of us — gardening rather than chess.

Rather than dictate the action, the leader creates the ecosystem that generates the right response and action. The gardener model leverages the talents of individuals and teams, rather than rely on the talents of the leader.

Instead of one general, there are hundreds distributed across the network. These could be individuals or teams. A distributed network of strong nodes is stronger and more agile than a concentrated network of one very powerful node but surrounded by weaker ones.

The notion of a gardener is not an altruistic or humanistic perspective, but rather about optimizing for pure performance in how a network responds to external stimuli, and how quickly it adapts to changing conditions.

The gardener creates an environment in which the plants can flourish. The work done up front, and vigilant maintenance, allow the plants to grow individually, all at the same time.

...I began to view effective leadership in the new environment as more akin to gardening than chess. The move-by-move control that seemed natural to military operations proved less effective than nurturing the organization—its structure, processes, and culture—to enable the subordinate components to function with “smart autonomy.” It wasn’t total autonomy, because the efforts of every part of the team were tightly linked to a common concept for the fight, but it allowed those forces to be enabled with a constant flow of “shared consciousness” from across the force, and it freed them to execute actions in pursuit of the overall strategy as best they saw fit.

Within our Task Force, as in a garden, the outcome was less dependent on the initial planting than on consistent maintenance. Watering, weeding, and protecting plants from rabbits and disease are essential for success. The gardener cannot actually “grow” tomatoes, squash, or beans—she can only foster an environment in which the plants do so.

As McChrystal points out, the gardener in a way cannot take "direct action". She/he is essentially creating the conditions to release the inherent energy of the system and helping it do what it's designed to do.

It's indirect action through controlling the context rather than the usual reaction of trying to directly control the situation.

Gardening is harder

Most leaders understand this difference intellectually but find it hard to implement in practice. Why? Couple of reasons stand out:

  • It requires unlearning the very habits that made them successful in the past — problem solving and inclination to take quick action.
  • It runs counter to common beliefs about the leader's job — they are expected to be all-knowing and neither do they don't want to appear incompetent.

However, these same strengths start impeding when working with highly talented teams who are capable of doing it themselves, but often need an overarching context aka ecosystem in order to operate at their highest levels.

Although I recognized its necessity, the mental transition from heroic leader to humble gardener was not a comfortable one. From that first day at West Point I’d been trained to develop personal expectations and behaviors that reflected professional competence, decisiveness, and self-confidence. If adequately informed, I expected myself to have the right answers and deliver them to my force with assurance. Failure to do that would reflect weakness and invite doubts about my relevance. I felt intense pressure to fulfill the role of chess master for which I had spent a lifetime preparing.

... But the choice had been made for me. I had to adapt to the new reality and reshape myself as conditions were forcing us to reshape our force. And so I stopped playing chess, and I became a gardener.

What the shift looks like

First I needed to shift my focus from moving pieces on the board to shaping the ecosystem. Paradoxically, at exactly the time when I had the capability to make more decisions, my intuition told me I had to make fewer. At first it felt awkward to delegate decisions to subordinates that were technically possible for me to make. If I could make a decision, shouldn’t I? Wasn’t that my job? It could look and feel like I was shirking my responsibilities, a damning indictment for any leader. My role had changed, but leadership was still critical—perhaps more than ever.

Creating and maintaining the teamwork conditions we needed—tending the garden—became my primary responsibility. Without my constantly pruning and shaping our network, the delicate balance of information and empowerment that sustained our operations would atrophy, and our success would wither. I found that only the senior leader could drive the operating rhythm, transparency, and cross-functional cooperation we needed. I could shape the culture and demand the ongoing conversation that shared consciousness required.

Leading as a gardener meant that I kept the Task Force focused on clearly articulated priorities by explicitly talking about them and by leading by example. It was impossible to separate my words and my actions, because the force naturally listened to what I said, but measured the importance of my message by observing what I actually did. If the two were incongruent, my words would be seen as meaningless pontifications.

The equivalent of gardening and creating an ecosystem in an organization is culture. But too often we don't see culture as actionable. How is a first line manager supposed to influence culture? Isn't that the CEO's job?

We feel we can't influence it because we don't think our actions are going to make a difference, leading to a "tragedy of the commons".

But in fast evolving complex systems, even the smallest actions can have large scale effects. The best way to influence the system is through our own actions. You are not stepping outside the system and acting "on" it per se. Rather you are what makes up the system, and thus any change you make also means the system changed, even if infinitesimally.

Gardeners plant and harvest, but more than anything, they tend. Plants are watered, beds are fertilized, and weeds are removed. Long days are spent walking humid pathways or on sore knees examining fragile stalks. Regular visits by good gardeners are not pro forma gestures of concern—they leave the crop stronger. So it is with leaders.

Tending takes a lot longer than planting and harvesting, and requires consistency and patience. There is no end or beginning to it. It's the day to day act of showing up, and responding to what shows up. That's also how culture and effective leadership are built — one interaction, one conversation at a time.

The leader's main job

The primary responsibility of the new leader is to maintain a holistic, big-picture view, avoiding a reductionist approach, no matter how tempting micromanaging may be. Perhaps an organization sells widgets, and the leader finds that he or she loves everything about widgets—designing, building, and marketing them; that’s still not where the leader is most needed. The leader’s first responsibility is to the whole.

... A leader’s words matter, but actions ultimately do more to reinforce or undermine the implementation of a team of teams. Instead of exploiting technology to monitor employee performance at levels ..., the leader must allow team members to monitor him. More than directing, leaders must exhibit personal transparency.

This holistic view is not that of a detached, removed approach where the leader focuses on everything "strategy". It's anything but that. In fact, it requires even more ground level engagement, but going about it in a different way than what we are used to.

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  • Critical feedback is hard to come by especially a you go higher up in leadership. Practicing with tools like The Johari Window Model can be useful.
  • Another analogy for how situations evolve and the pace of adapting is thinking in terms of Tetris rather than chess. There are dynamics unique to Tetris that is more relevant to modern work than chess.
  • Leaders, often by default, think naturally in terms of control and content, rather than context. Managing context is a meta-skill that unlocks several others both in leaders and their teams. Gardening is a fitting metaphor that captures the underlying dynamics of context and effective leadership.


  1. Team of Teams by General Stanley McChrystal with Tantum Collins, David Silverman, Chris Fussell.
  2. Tools of Titans by Tim Ferriss.

Video: Listen then lead by General Stanley McChrystal

Sheril Mathews
I am an executive/leadership coach. Before LS, I worked for 20 years in corporate America in various technical & leadership roles. Have feedback? You can reach me at
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