Strategy in Action

How To Be (More) Certain To Succeed

Erik Schön
An Idea (by Ingenious Piece)
11 min readAug 21, 2020


Would you like a quick, hands-on introduction to strategy? Then, please join me on this tour over 2 500 years where we discover eternal, universal patterns and examples useful for individuals, teams, and organizations — starting from purpose via strategic learning loops to maps that visualize your evolving business and technology landscape.

How Can We Be (More) Certain To Succeed

Parts of the world have always been volatile, uncertain, complex, and ambiguous — think of tsunamis, freak waves, wars, the Black Death in Europe in the Middle Ages, …

The Wave of the Future — Digital Transformation of The Great Wave. Illustration: Kirpich and Berry

Now, the digital transformation towards software and world-wide communication is increasing the speed by several orders of magnitude since its travels so much faster than atoms. Organizations are struggling to cope with the massive changes in customer behaviors and business models that this entails.

So, in a world where the rate of change will never be slower than today, how can we be more certain to succeed?

The answer — going back at least 2 500 years to Sun Tzu — is strategy. You can never be completely certain, but you can create conditions for stacking the odds in your favor, e.g. through assessments and preparations, situational awareness, and gameplays.

Assessment and Preparations: Five Fundamental Factors

“Master the five fundamental factors to succeed, or else, fail.” Sun Tzu

Sun Tzu: general and strategist, c. 544–496 BC. Photo © Keren Su

The Art of War written by the Chinese general Sun Tzu around 400 BC is about how to be certain to win and avoid fighting wars, and, if forced to fight, to do it with speed, surprise and adaptability.

The eternal, universal wisdom of Sun Tzu — applied throughout the ages by military officers, politicians, CEOs, non-governmental organization officials, and startup founders — tells us to start our journeys by assessing and preparing by considering the following five fundamental factors and the corresponding questions:

  • Who has a more influential purpose?
  • Who is favored by landscape?
  • Who is favored by climate?
  • Who carries out doctrine more skilfully?
  • Who has more skilled leadership?

Master, all five to be (more) certain to succeed even before you start your journey.


This is your higher meaning or reason for existing that keeps people united supporting each other without fear through success and failure. It gives you direction just like a compass.

Chinese compass, c. 220 BC. Photo: National MagLab

Compasses date from c. 400 BC when Chinese Jade hunters carried a “south pointer” to prevent them from getting lost during their journeys.


  • Alzheimer’s Association: A world without Alzheimer’s disease.
  • IKEA: To create a better everyday life for many people.
  • Tesla: To accelerate the world’s transition to sustainable energy.


This is the business and technology environment — we’ll talk more about this in the section on Gameplays below.


These are the forces acting on the environment including technology evolution and stakeholders’ actions — we’ll talk more about this in the section on Gameplays below.


These are your ways of operating, organizing and communicating that apply irrespective of landscape and climate.

Example: Software Engineering at MercadonaTech. Illustration: Miquel Torres

Example: Mercadona Tech’s software engineering doctrine where the principles and practices of Extreme Programming (XP) are combined with an internal open-source model to avoid dependencies and blocking, and, product engineers who care about both customers and the product, and, collaborate closely with product managers and designers to solve the right problems in the right way.

Example: Below we see another organization’s visualization of its doctrine that can be used to assess and improve. The graph shows the capabilities — and how they depend upon each other — needed to fulfill the mission of being excellent at doing software development.

Example: Visualising doctrine in a software organization — the universally applicable principles (“what” and “why”). Illustration: Erik Schön

The illustration below shows examples of specific practices and tools (the “how”) that could be used to fulfill the principles (the “what” and “why”) in the doctrine.

Example: Wardley’s Doctrine below lists a number of principles for successful operation classified into six categories based on Simon Wardley’s (swardley) experiences over the past 20+ years.

Example: Wardley’s Doctrine. Source: Simon Wardley (swardley, CC BY-SA 4.0)

An organisation aspiring for success should evolve their own doctrine — inspired by the examples above, and, skilled, experienced product development leaders and researchers like Don Reinertsen, Marty Cagan, JanBosch and Bob Marshall.


These are the actions, decisions, choices and gameplays based on purpose, landscape, climate and doctrine. This is not restricted to specific roles, but something you would like all the smart, creative collaborators in the organisation to do every day.

Curious question: What does your organisation’s purpose, doctrine and leadership look like?

Situational Awareness: The OODA “Loop”

“… who can handle the quickest rate of change survives …” John R. Boyd

John R. Boyd: fighter pilot and strategist (1927–1997). Photo: US Department of Defence

This is John R. Boyd: fighter pilot, instructor, tactician and analyst; “father” of the F15, F16 and F18 fighters, and, one of the top strategists of the 20th century. Inspired by Sun Tzu, his two-day briefing A Discourse on Winning and Losing shaped the US Marine Corps’ doctrine, the first Iraq war strategy and has been widely applied in diverse fields of conflict such as business, sports and politics.

Boyd’s OODA “Loop”

John Boyd invented the OODA “loop”, a schematic representing three processes and their interplay for:
• implicitly using your existing capabilities;
• creating new and unexpected ways of using existing capabilities;
• creating completely new capabilities;

It is often visualized as a “loop” consisting of four distinctive although connected activities — Observation, Orientation, Decision and Action — but it’s actually a combination of several feedback and feed-forward loops as illustrated below.

Observation is sensing yourself and the world around you.

Orientation is a complex set of filters of genetic heritage, cultural predispositions, personal experience and knowledge, and, analysis and synthesis in order to create new capabilities to deal with unfamiliar phenomena or unforeseen change.

The decision is a review of alternative courses of action and the selection of the preferred course as a hypothesis to be tested.

Action is testing the decision selected through an experiment.

“Loop” means that observation, orientation, decision and action are repeated again and again. You are simultaneously observing any mismatches between your conception of the world and the way the world really is, trying to reorient and attempt to come up with ideas to deal with it. Success depends upon the quality and tempo of the cognitive processes of leadership and the organisation; it is crucial to secure higher tempo and/or more variety in the rhythm of the OODA loop than competition. “Getting inside or operating inside your competitors’ or customers’ OODA loops” includes shaping their orientation as well as using information from intelligence operations.

OODA “Loop”. Illustration: John Boyd

These strategic “loops” will help you learn and adapt better than the competition while keeping competition off balance.

Example: Amazon — faster, cheaper and better. Photo © Amazon

Example: Amazon learns and adapts better than the competition by being faster, cheaper and better in both developing and delivering products time and time again, thereby catching up, overtaking and extending their lead relative to their competitors.

Example: Strategy retro-/prospectives for quarterly strategy and target updates. Illustration: Peter Högberg and Erik Schön

Example: A large telecom vendor just north of Stockholm is doing regular strategy retrospectives/prospectives in several product development leadership teams in order to learn and adapt better than competition. These are done once every quarter, hence a move from the classic yearly strategy cycle to quarterly cycles, leading to better choices, decisions, actions thanks to more regular updates of everyone’s orientation/situational awareness. And, by having a diverse team interacting in a safe environment, we will get additional perspectives on the table which leads to even better choices, decisions and actions.

Example: Daily Management to learn and resolve issues quickly. Illustration: Erik Schön

Example: A heavy truck maker south of Stockholm has extended the daily standup meetings from development teams to all leadership teams on all levels in the R&D organisation calling it “Daily Management”. The few deviations and issues that cannot be resolved in the development teams’ standup meetings are “popped” to the next level, and so on, all the way to the CTO’s leadership team’s 15-minute standup 45 minutes later. The idea is to resolve issues quickly while they’re still small, to resolve issues at the right place where the right competence exists, and, to collaborate across teams and organisation borders to resolve issues. In some large organizations, it would takes days if not weeks to get the right people in the same room at the same time to resolve cross-organizational issues due to too many meetings.

Apple iPhone 2007 — keeping competition off balance using surprise. Photo © Apple

Example: Apple kept competition off balance when releasing the first iPhone in 2007 with the expected: a phone that you could make calls with, a handheld device that you could browse the web and read mail with and a music player that could fit in your pocket, and, it all just worked; the positively surprising was that all this was in one device with an awesome touch interface, resulting in “desire to use” and extreme customer loyalty.

Curious question: How does your organisation learn and adapt in order to sustainably thrive?

Gameplays to Shape the Business Landscape

“Strategy is the art of manipulating an environment to gain a desirable outcome.” Simon Wardley

Simon Wardley: founder, CEO and strategist (swardley)

In order to make the most suitable strategic gameplays, it helps by visualising the business and technology landscape and how it evolves.

Inspired by Sun Tzu and John Boyd, Simon Wardley — founder, CEO and strategist — has invented Wardley Maps to help us do exactly this.

Visualising the World Using Maps

Let’s look at a classic way of visualising the world for increased understanding and decision support: maps.

Map of Shanghai from 1814. Source: Katya Knyazeva. Illustration: Erik Schön

A map is visual, context-specific (in this case of the old town of Shanghai in 1814) showing position and components (here: the location of houses, roads, walls, rivers, bridges, …) and movement (“getting to X”) including an anchor (the Chinese sign for “north” at the top).

Geographical maps encode information about a given context much more efficiently and clearly than words written or spoken. Reading a map requires you to study and understand the language of maps, and, of course, practice using maps.

Visualising Strategy Using Wardley Maps

Geographical maps are visualisations of the world that guide us from A to B. Wardley Maps are visualisations of the technology and business landscape for a specific context showing technology and business evolution and guiding our strategic choices of what to do and not to do, i.e. our gameplays.

Wardley Maps help us explore the present in order to:

  1. Anticipate the future by observing the climatic patterns of the business world, e.g. supply and demand competition evolving products from ideas to commodity, and,
  2. Shape the future using different strategic gameplays

by answering the following questions:

  • What do our customers need, today and tomorrow?
  • What is our competitive environment? Where are we?
    Where’s competition, today and tomorrow?
  • What market, business and technology changes can we anticipate?
  • Where do we focus?
  • Where can we expect inertia?
  • Which choices are possible for us?
  • What do we own and what do we develop in-house?
    What do we buy off-the-shelf and what do we outsource?
  • Which methodologies do we need?
    How can we organise to accommodate continuous change?
  • What capabilities do our teams and our organisation need for the products and services we are developing, today and tomorrow?

Wardley Mapping enables collaboration for improved predictions and shaping the future by helping participants articulate, share and assess their perceptions and understanding of the environment. This leads to a common, shared context specific language and a common, shared visualisation that can be used to guide decisions and actions on what to do. It also makes implicit assumptions explicit in an object — the map — which is much more easy to challenge than a person.

Example: Here’s an example of a Wardley Map visualising the context of online gaming.

Wardley Map of online gaming. Abbreviations: PSN (Play Station Network), CDN (Content Delivery Network), API (Application Programming Interface). Illustration: Howard Rees

The vertical axis shows needs where needs at the top are fully visible to your customers all the way to components completely invisible and far away from your customers.

The horizontal axis shows the evolution of the components:

  • Genesis: the unique, the very rare, the uncertain, the constantly changing and the newly discovered. Our focus is on exploration.
  • Custom Built: representing the very uncommon and that which we are still learning about. It is individually made and tailored for a specific environment. It is bespoke. It frequently changes. It is an artisan skill.
  • Product (+ rental): the increasingly common, the manufactured through a repeatable process, the more defined, the better understood. Change becomes slower here. Whilst there exists differentiation particularly in the early stages there is increasing stability and sameness.
  • Commodity (+ utility): scale and volume operations of production, the highly standardised, the defined, the fixed, the undifferentiated, the fit for a specific known purpose and repetition, repetition and more repetition.

The customer is the anchor of a Wardley map, similar to north in geographical map. We also see components (e.g. “Content”) and their positions and relationships, e.g. how “Content” needs or depends upon “CDN (Content Distribution Network”). These relationships form a value chain — a chain of needs — with customer needs and components arranged according to dependency — running from needs visible to the customer in the uppermost part of the Wardley Map to components least visible in the lower part of the map. And, finally, the red arrows show the evolution of components from uncharted to industrialised territory.

Curious question: How does your organisation visualise the evolving business and technology landscape in order to make suitable gameplays?


  1. Assess and prepare yourself using the following five fundamental factors: purpose, leadership, doctrine, landscape and climate.
  2. Create shared situational awareness together in order to learn and adapt using OODA loops.
  3. Visualise business and technology evolution using Wardley Mapping — together.

For Further Inspiration and Learning

You can find my work on leadership, strategy and Lean/Agile, e.g. the books The Art of Strategy and The Art of Leadership, at Yokoso Press, Medium, SlideShare and YouTube.

Additional articles, books, presentations and videos for further inspiration and learning below.


Bosch (JanBosch): Beyond Agile
Richards: Boyd’s OODA Loop
Schön (Erik Schön): Doctrine or Dogma?
Schön (Erik Schön): Doing Strategy the Interactive & Flexible Way
Schön (Erik Schön): Seeing Around Corners
Torres (Miquel Torres): Engineering at MercadonaTech
Wardley (swardley): My Basics for Business Strategy
Wardley (swardley): An Introduction to Wardley Mapping

Awesome List

Wardley Maps


Boyd: A Discourse on Winning and Losing
Cagan: Inspired — How To Create Tech Products Customers Love
Lao Tzu (Editor: Erik Schön): The Art of Leadership
Marshall (Bob Marshall): Product Aikido — The Exemplar Doctrine
Reinertsen: Principles of Product Development Flow
Sun Tzu, Boyd & Wardley (Editor: Erik Schön): The Art of Strategy
Wardley (swardley): Wardley Maps


Borchardt (sue borchardt): Getting Strategic on Peace and Justice
Lamb: Investing in Innovation
Schön (Erik Schön): Doctrine or Dogma?
Schön (Erik Schön): The Art of Strategy — Steps Towards Business Agility
Wardley (swardley): Crossing the River by Feeling the Stones


Simon Wardley (swardley), Marc Burgauer and Bob Marshall for inspiration around strategy, doctrine and Wardley Mapping.

Björn Tikkanen, Henrik Kniberg and Jonas Boegård for encouragements to write things up.

This is provided as Creative Commons Attribution-ShareAlike 4.0 International by the author, Erik Schön.



Erik Schön
An Idea (by Ingenious Piece)

From hacker, software researcher and system engineer to leader, executive and strategizer. Writer: #ArtOfLeadership #ArtOfStrategy