Monastic Strategy

True confession: I don’t really care about devops. I’m not in the tech industry and it doesn’t affect me directly on a day-to-day basis. So why did I fly 2500 miles to go to a whole conference dedicated to devops?

As the Assistant Director of the Monastic Academy, my job is to help our monasteries flourish. Our vision is to create a contemplative culture for the modern world. Getting there involves tactical meetings, tax returns, and above all, strategy.

I became interested in strategy by way of Wardley Mapping. devopsdays Atlanta was hosting a track about Wardley Mapping, and I had been invited to present on Burja Mapping, a method for mapping power.

Why is a monk interested in strategy?

Strategy was largely developed in two domains: warfare and business. But there’s nothing intrinsically violent, war-like, or even zero-sum about strategy. I often say that if you become interested in meditation, as I have, you will inevitably encounter Buddhism. As a contemplative tradition, Buddhism has taken meditation and meditation instruction quite far. But you don’t need to become a Buddhist to meditate. Similarly, if you are interested in strategy, you will inevitably encounter military and business strategy. That doesn’t mean you need to enlist in the military, or sprout pointy hair. Those domains have simply developed strategy to a very high degree.

At the Monastic Academy, many of the questions we face from week to week, year to year are strategic in nature:

  • How should we decide which problems to solve, which projects to prioritize?
  • What is our bottleneck? Is it trainees, property, or funds? And what should it be?
  • How should we organize ourselves as a team?
  • How can we use work as an opportunity to grow individually?
  • Where does organizational culture come from?
  • How can we acquire resources in an ethical and efficient way?
  • How should we collaborate with other organizations?
  • What is the most effective and sustainable way to scale our monasteries exponentially?

I’ve looked to military and business strategy for help answering these questions. The authors that have most informed my thinking have been Sun Tzu and John Boyd, Simon Wardley and William Dettmer. I’ve also been grateful to have the support of my friend and mentor Ben Mosior.

I’ve tried to transpose strategic thinking from the military and business context into monasteries. Happily, there are often low-hanging fruit, which solve the problems we’re facing quite effectively.

Gaining competency in the art of strategy has taken extensive research and experimentation. I’ve spent hours going down rabbit holes of PDF’s and YouTube videos. I’ve made painful mistakes that still cause pangs in my stomach, months later. Even after I’d found a useful set of tools, it wasn’t clear to me which tool to use, when – or how they all related to each other.

If you’re interested in strategy, this post will be valuable to you. Maybe you’re a leader, or want to be one. Maybe you’re doing important work, that simply must succeed. Maybe you’re working with multiple people, or you’re doing work over long time scales.

Whatever the reason, I hope this post will save you some time, spare you some mistakes, and give you a big picture of how different strategy tools relate to each other. It shares the answers that I’ve found to the questions above, and the tools I’ve found most valuable so far:

  • Cynefin
  • Iteration
  • Conditions/Consequences
  • The Expected and the Unexpected
  • Wardley Mapping
  • Burja Mapping
  • The Theory of Constraints
  • The Logical Thinking Process
  • Alliances
  • SWOT
  • Westrum Typology
  • Commander’s Intent

I won’t explain each tool in extensive detail. For the most part, others have already done that, and I’ll link to their work. In the few places where I’ve found holes, I have written blog posts, or will in the future.

Strategy Tools and Concepts

Concepts are useful, but it’s even more useful to know the circumstances when those concepts are useful. Duct tape is good for sticking things together, WD40 is good for lubrication, and Wardley Maps are good for “things you don’t understand but should.” If you know that a tool is useful in a certain setting, you don’t need to be a master of that tool. You might not even need to know how to use it. You can learn it just-in-time.


Cynefin (pronounced like “kenevin”) is the Welsh word for “habitat.” For our purposes, it is a simple but powerful framework for making sense of problems. It’s often the first thing I share with someone interested in strategy.

Cynefin, Wikipedia

First, it helps you diagnose what kind of problem you are facing:

  • Disorder is when you don’t know what kind of problem you have.
  • Obvious problems have simple, well-known solutions. Being hungry means you should eat some food.
  • Complicated problems have known solutions that aren’t easy. Usually, this means either that you should hire someone who is an expert in the relevant domain, or that you should solve it yourself, knowing that you’re getting yourself into a messy situation that might just give you a headache. But you’ll learn a lot!
  • Complex problems don’t have well-known solutions, but are subject to the laws of cause and effect. Do several easy, cheap, safe-to-fail experiments. Listen to what happens, using stories as a guidepost. Look for more stories like THIS, and fewer stories like THAT. If one works, keep going. If one doesn’t, stop!
  • Chaotic problems have no known solutions and don’t obey the normal laws of cause and effect. This is a highly unstable environment, and any action is better than inaction. Take quick, decisive action and try to get out of the chaos as soon as possible with as little damage done as possible.

Each of these diagnoses naturally suggests how you might approach a solution.

Cynefin also provides a scaffold which helps you understand other, more complicated strategic tools. For example, I find implementation trees, a tool from the Logical Thinking Process (described below), useful in the complicated domain. I allude to the Cynefin framework in many of the descriptions below.


Strategy is iterative. You don’t make a “big strategy” and then leave strategizing behind, always trying to execute on the same plan. Strategy is iterative – you sense into the present, try to make sense of what’s happening, make a decision, and then act on it – and then repeat that same cycle.

This insight, that strategy is iterative, is the core of John Boyd’s OODA loop. OODA is an acronym for Observe, Orient, Decide, and Act. This can be as simple as cycling through these steps, but these simple elements can become much more complex.


Much of strategy is concerned with accomplishing goals. Unfortunately, our default approach to accomplishing our goals is suboptimal.

Most people try to achieve a certain goal (end) and find a way to get there (means). This approach does work. That’s why it’s at the core of most organizational goal-setting rituals. But it is very fragile. It tends to work well in the simple or complicated domains, but does not do well in complex situations. The best laid plans often prove to be shiny, brittle failures.

Instead, it’s better to recognize that the future is uncertain. There are many possible outcomes; it’s difficult to predict what will happen. Knowing that, you can cultivate the conditions that will lead to good consequences in most scenarios. This is the conditions-consequences model, which Callum Flack describes in Notes on Deciphering Sun Tzu and I write about in the Means-Ends, Conditions-Consequences, and the Game of Risk.

I’ve found that a mix of these approaches is the most resilient approach. Know your goals, but don’t get tied to them. Be willing to adapt: to add, drop goals on the fly, and totally rearrange circumstances. Be aware of what things – skills, relationships, internal efforts etc – you can count on being valuable even if you don’t know how in advance. For example, cultivating the skills I describe in this post!

The Expected and the Unexpected

This phrase comes from the Chinese words cheng and ch’i. These words are sometimes translated as the expected and unexpected, or as the orthodox and unorthodox.

This concept is very straightforward to understand. For example, Teslas have standard car features like chairs, but also include ‘bioweapon defense mode’ buttons. Chairs are expected. Biohazard modes are unexpected.

Mastering standard operating procedure is table stakes for competition. Competitors who also have a flair for the dramatic and unexpected will consistently beat those who merely do what is standard practice.

In my line of work, it’s actually quite easy to notice opportunities to do the unexpected. Because we are doing monastic training, if you combine that with anything that breaks people’s mental model of what monks do, it is by definition the unexpected. This effect is even stronger because monks are relatively rare. For example, there are many high-quality articles about strategy, but there are very few which discuss strategy from the perspective of monasteries – therefore this blog post makes use of both the expected (good writing, or so I hope) and the unexpected (strategy monk!).

Wardley Mapping

Ben Mosior says that Wardley Maps help you understand things you don’t, but should. The first thing Wardley Mapping provides is a visual artifact, with two axes.

The first axis is the value chain, for how you meet the needs of a user through various components. Those components are more or less visible to the user.

The second axis is the evolution axis, which describes which components are in which stage of evolution under supply and demand competition. Is a component brand new, and not well understood? Or is it more like electricity, which is ubiquitous and well understood?

A whiteboard Wardley Map about documentation at the Monastic Academy

Once I’ve made a Wardley Map, it helps me to make a better decision. The most basic use case is to answer the question “Should i make this component myself, or outsource it to a product or service?” You don’t want to make your own electricity, but you may want to write your own custom software.

This kind of decision-making is useful for me individually, but it’s also useful as a group. Making decisions as a group can be a long, confusing, frustrating process. Having an artifact handy, even a very rough one, simplifies group decision-making dramatically. It becomes much easier to have a calm and efficient reflection on what’s so and what’s next.

There’s even more to learn about Wardley Mapping beyond the artifact itself. There’s a larger mindset behind using them strategically that’s worth diving into. But I’d recommend learning to make the maps first, and learning that later.

Burja Mapping

To accomplish important efforts, you will need to understand power. You will need to acquire political capital, and use it to bring about a meaningful vision.

Samo Burja’s Empire Theory has helped me to understand power dynamics in my own organization. It’s also proved useful for interpreting the workings of other organizations we’ve encountered. I’ve found it useful to make visual representations of these landscapes of power, which I call Burja Maps.

A Burja Map of Wardley’s Scenario and analysis

Burja Maps help you to interpret the current power landscape, and decide how to move forward. You want to come to the point where you can see these power dynamics with ease. It’s as if you were doing a math problem with mental math – no pen and paper needed. When this skill is that easy, that fluid, you can begin to develop your own intuitions for the power dynamics Samo describes briefly in his paper, Great Founder Theory.

The Theory of Constraints

Maybe you’ve heard the word “bottleneck” used before. A bottleneck constrains how much fluid can be poured out of a jar. The Theory of Constraints posits that every system has a constraint.

You do not want to eliminate the constraint. That is impossible. There will always be a constraint. You want to know what your constraint is, and make best use of it, until it is no longer the constraint – something else is.

For much of my time at the Monastic Academy, our bottleneck has been residents in training. We often had shortages of how many people could do the work needed.

This shortage was partly caused because we require new residents to commit to a minimum of one year of training. When we realized that, we created an apprentice program, where people come for three months as a first step. At the end of that time, we can decide together whether a full year of training is the next step for each individual candidate.

As far as I can tell, this change has caused our bottleneck to switch from people to money. I think our current constraint is funding. This is progress, but not ideal.

We want to come to the point where our bottleneck is how many qualified teachers we have available to start and run monasteries. A qualified teacher in our tradition has a deep meditation practice, as well as a mastery of the many diverse skills needed to effectively run a monastery. If there is ample demand for the services of such rare individuals – more than we can meet – the bottleneck will be in the right place. At that point, we will have succeeded.

The Logical Thinking Process

The Logical Thinking Process emerged from the Theory of Constraints. It contains five separate tools for solving complex system problems. Each tool has a different purpose, which answers a different question, which William Dettmer describes as follows:

  • Goal Tree – Where do we want to be?
  • Problem (Current Reality) Tree – Where are we, actually, and why is there a difference?
  • Conflict Resolution Diagram (Evaporating Cloud) – What prevents us from curing the problem now, and how do we overcome it?
  • Solution (Future Reality) Tree – What can we expect to happen if we apply a “fix” to the problem?
  • Implementation (Prerequisite) Tree – How do we make the solution happen—that is, execute the solution?

Figure 1.2 from The Logical Thinking Process – An Executive Summary

These tools were originally designed to be used in sequence, but I tend to use them separately. I’ve made the most use of conflict resolution diagrams, implementation trees, and problem trees, in that order. I wrote more about how I use those tools and the Logical Thinking Process in general in The Punk Strategy Guide to the Logical Thinking Process.


Succeeding in any strategic endeavor will require alliances with other actors. Those actors might be in your organization, and they might be outside of it. Either way, you want to stay in touch with your allies, and find win-win outcomes as frequently as possible. With larger numbers of allies, this becomes increasingly feasible. It also becomes more satisfying.

Humans are complex. Accordingly, there is an art to alliances.


When I first heard of SWOT (Strengths, Weaknesses, Opportunities, and Threats analysis), I thought it was sort of stupid. Like many 2×2’s, it can be used blindly. Moreover, I was confused by the word “Opportunities” and “Threats.” I wasn’t sure from those terms how they differed from Strengths and Weaknesses.

However, when I started exploring Burja Mapping, I realized that SWOT’s are actually incredibly useful. Burja Mapping helps us to understand the landscape of power. From that place, we can begin to understand people’s strengths and weaknesses in a useful way. As Simon Wardley says, “The problem with SWOT isn’t that it is useless but instead we apply it to landscapes we don’t understand.”

I find it easier to think of Opportunities as Objectives, and Threats as Traps. What goals does a person have? Given their strengths, weaknesses, and goals – and your own – what traps might you two fall into together?

A sample SWOT diagram

I’ve found it very useful to think about the people inside of my organization in terms of SWOT’s. As Empire Theory points out, this is also useful for outside actors. Finally, it can also be useful to consider the SWOT’s of teams or organizations.

I write about SWOT’s more in On the Use and Abuse of SWOT Diagrams.

Westrum Typology

In 2004, Ron Westrum published a paper, A typology of organisational cultures (notes). It posits that the habits an organization has around information sharing are predictive of many elements of an organization’s culture. It also included a typology for comparing organizations and their cultures.

Example output from the Westrum Typology Cheat Sheet (repository)

The Westrum Typology has been extremely useful for understanding many things, but in particular, it helped me to understand how to collaborate and coordinate effectively with other organizations. In particular, fast information flow is extremely important. Constantly be asking “who needs this information now?,” and be sure that that information flows to the relevant individuals or groups, even if backchannels are needed. I wrote more about the Westrum Typology here.

Commander’s Intent

Leadership is challenging. It’s easy for me personally to fall into a common trap: micromanaging. The other risk is that I will overcompensate for avoiding micromanagement, and basically leave subordinates to their own devices, without any input or feedback.

Commander’s intent strikes a terrific balance between these two failure modes.

Intent is the best approach to use when there is trust between commanders and their subordinates. This takes months and years to develop.

If that trust is present, each project and circumstance is an opportunity for the leader to communicate their intent. They should tell their subordinates everything they need to know: what their goals are, any relevant facts and figures, any hard constraints or needs… Then, when both the commander and subordinate have a shared sense of understanding, the subordinate can elect to accept or decline the mission.

A Colonel shares an intent in the military recruiting context

If the subordinate declines the mission, it means that they have serious reservations and many things need to be reconsidered. Doing so should be the exception rather than the norm.

If they accept the mission, there is a shared understanding that the subordinate will do everything in their power to realize their commander’s intent. The commander doesn’t care how the mission is accomplished, so long as it is accomplished. The subordinate can use all of their creativity – and their on-the-ground understanding of what’s really needed – to do so.

In the military domain, being out of contact is a frequent occurrence in battle. In the monastic setting, people are often out of contact when they are on meditation retreat. Either way, Commander’s Intent allows things to adjust and degrade gracefully.

If that kind of trust is not present, it’s better to err on the side of micromanagement. There’s a skill in learning how to roll up your sleeves and get detail-oriented, as a manager, without having pointy hair shoot out of your skull.

Commander’s Intent is useful not only for leaders, but also for followers. As a follower, your goal should be to have complete understanding of your commander’s intent, and to be able to creatively execute that intent using your own intuition as well as any emergent circumstances.

One is always a leader in some contexts, and a follower in others. That’s why it is useful to master following, so that you can lead well – and master leading, so you can follow well.


The tools and concepts I’ve shared here are the ones I’ve found most useful so far. I’m sure I’ll add (and create!) more in the future, and will continue to share my learnings.

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