The Art of Strategy: Engagement

7. How to engage using surprise

Photo: Inggrid Koe on Unsplash

What is strategy? Why do you need it? How do you do it? And, how can you be more certain to succeed? The Art of Strategy provides timeless answers to these eternal questions. It is a modern reading of Sun Tzu’s Art of War using the lenses of strategists John Boyd and Simon Wardley (swardley). All parts. Other reading and viewing formats.

Sun Tzu

To successfully deploy strategy:
agree on purpose with stakeholders;
recruit and train people based on purpose and doctrine;
structure the organization and ways of operating based on purpose and doctrine.

Engagement with competition is the most difficult part of strategy deployment.

Photo: Mark König on Unsplash

The difficulty is turning devious routes into direct, shortcuts into delays, adversity into advantage.

Offer what looks like advantages to shape competition’s perspective and movement, changing what is easy into what is difficult.

And so, reach success before competition even though at first seemingly lagging behind.

This is mastering the devious and the direct.

爭 (Zhēng) Engagement. Calligraphy © Hisayo Oki

Engagement has advantages and risks:

moving too fast into a new area brings losses of every kind
— psychological, social and financial;

the further away from existing areas, the higher the risk of losses.

Losing its service functions, the organization is lost.

Knowing competition’s intentions enables alliances;
knowing the landscape enables movement;
knowing local conditions enables advantageous positions.

Strategy deployment is based on shaping:

Photo: Inggrid Koe on Unsplash

hide intentions and use surprise;
move based on advantages;
change situations by dispersion and concentration.

Swift like the wind,
slow like the forest.

Aggressive like fire,
firm like the mountain.

Formless like darkness,
moving like thunder.

After moving into new areas, divide the gains from success.
Assess the situation, then decide and act.
Master the devious and the direct to ensure success.

This is engagement.

When communicating, use common language and visualization to secure harmonized actions, decisions and choices.

When united in purpose and doctrine, the organization moves together as one — sharing success and failure.

Adjust communication to the needs of stakeholders to secure unity of purpose and doctrine.

This is deploying strategy in large organizations.

An organization can lose its spirit. Leadership can lose passion.

Spirit changes in cycles:
in the beginning spirit is high,
then it begins to fade,
towards the end it is drained.

Avoid competitors when their spirit is high;
move when their spirit is drained;
this is mastering spirit.

Disciplined, wait for disorder;
calm, wait for commotion;
this is mastering emotions.

Near, wait for the distant;
rested, wait for the fatigued;
full, wait for the hungry;
this is mastering resilience.

Avoid engaging when competition is well-ordered;
avoid engaging harmonized setups;
this is mastering adaptations.

This is how to engage:
avoid engaging competition holding high ground;
avoid engaging competition with their back against the wall;
avoid following retreating competitors;
leave an outlet when competition is surrounded;
avoid pressing competition that is cornered.


From A Discourse on Winning and Losing.

Patterns for Successful Operations
Goal: diminish adversary’s freedom-of-action while improving our freedom-of-action, so that our adversary cannot cope — while we can cope — with events/efforts as they unfold.


  • Probe and test adversary to unmask strengths, weaknesses, maneuvers, and intentions.
  • Employ a variety of measures that interweave menace–uncertainty–mistrust with tangles of ambiguity– deception–novelty as basis to sever adversary’s moral ties and disorient or twist his mental images, hence mask–distort–magnify our presence and activities.
  • Select initiative (or response) that is least expected.
  • Establish focus of main effort together with other (related) effort and pursue directions that permit many happenings, offer many branches, and threaten alternative objectives.
  • Move along paths of least resistance (to reinforce and exploit success).
  • Exploit, rather than disrupt or destroy, those differences, frictions, obsessions, etc., of adversary organism that interfere with his ability to cope with unfolding circumstances.
  • Subvert, disorient, disrupt, overload, or seize adversary’s vulnerable, yet critical, connections, centers, and activities that provide cohesion and permit coherent observation–orientation–decision–action in order to dismember organism and isolate remnants for absorption or mop-up.

Action: observe-orient-decide-act more inconspicuously, more quickly, and with more irregularity as basis to keep or gain initiative as well as shape and shift main effort: to repeatedly and unexpectedly penetrate vulnerabilities and weaknesses exposed by that effort or other effort(s) that tie-up, divert, or drain-away adversary attention (and strength) elsewhere.


  • superior mobile communications
  • only essential logistics

to maintain cohesion of overall effort and sustain appropriate pace of operations within available resources.


  • Decentralize, in a tactical sense, to encourage lower-level commanders to shape, direct, and take the sudden/sharp actions necessary to quickly exploit opportunities as they present themselves.
  • Centralize, in a strategic sense, to establish aims, match ambitions with means/talent, sketch flexible plans, allocate resources, and shape focus of overall effort.

Essence of Moral Conflict

Essence of Moral Conflict. Illustration: John Boyd, Patterns of Conflict

Appropriate Bits and Pieces

  • Compress own time and stretch-out adversary time.
  • Generate unequal distributions as basis to focus moral–mental–physical effort for local superiority and decisive leverage.
  • Diminish own friction (or entropy) and magnify adversary friction (or entropy).
  • Operate inside adversary’s observation — orientation–decision–action loops or get inside his mind–time– space.
  • Penetrate adversary organism and bring about his collapse.
  • Amplify our spirit and strength, drain-away adversaries’ and attract the uncommitted.

Central Theme

Evolve and exploit insight/initiative/adaptability/harmony together with a unifying vision, via a grand ideal or an overarching theme or a noble philosophy, as basis to:

  • shape or influence events so that we not only amplify our spirit and strength but also influence the uncommitted or potential adversaries so that they are drawn toward our philosophy and are empathetic toward our success,

yet be able to

  • Operate inside adversary’s observation–orientation–decision–action loops [OODA “loop”] or get inside his mind– time–space as basis to:
  • Penetrate adversary’s moral–mental–physical being in order to isolate him from his allies, pull him apart, and collapse his will to resist.


From Wardley Maps.

Climatic Patterns for Engagement
Competitors’ actions will change the game. Climatic patterns are ones that depend upon aggregated market effects e.g. evolution through supply & demand competition. This means that you cannot stop them without preventing competition in the market and the existence of competitors will cause them to happen.

Most competitors have poor situational awareness. Competitor actions are an important part of anticipation. In general however this is not something that you can directly control or even anticipate beyond aggregated effects. Fortunately in today’s climate then most competitors act as blind players in which case you do not need to dwell too much on their actions. When you make a move, they are unlikely to understand why or counter you. In the near future, given the potential interest in business algorithms, they maybe even become anticipatable blind automatons following coded secrets of success.

Capital flows to new areas of value. The lines on the map represent flows of capital whether it’s between two existing components or a component and its future more evolved self. Financial capital will seek the area of most consistent return. Hence in the evolution from product to a utility then capital will tend to move away from the pre-existing product forms and towards the more industrialized component and the new industries built upon it.

Doctrine for Communication
Focus on high situational awareness. There is a reasonably strong correlation between situational awareness — our level of understanding of context (purpose and landscape), and, how context is changing — and business performance, so focus on this. Try to understand the landscape that you are competing in and understand any proposals in terms of this. Look before you leap.

Different aspects of situational awareness in an organization. Illustration: Simon Wardley (swardley, CC BY-SA 4.0)

Use a common language. A necessity for effective collaboration is a common language. Maps allow many people with different aptitudes (e.g. marketing, operations, finance and IT) to work together in order to create a common understanding. Collaboration without a common language is just noise before failure.

Wardley Maps — a common language for effective collaboration. Illustration: Simon Wardley (swardley, CC BY-SA 4.0)

Challenge assumptions. Maps allow for assumptions to be visually exposed. You should encourage challenge to any map with a focus on creating a better map and a better understanding. Don’t be afraid of challenge, there is no place for ego if you want to learn.

Be transparent. Have a bias towards openness within your organization. Sharing a map will enable others to challenge and question your assumptions. This is essential because it helps us to learn and refine our maps. The downside of sharing is it allows others to challenge and question your assumptions. Many people find this uncomfortable. Don’t underestimate how difficult this transparency is within an organization.

Provide purpose, mastery and autonomy. Provide people with purpose (including a moral imperative and a scope) for action. Enable them to build mastery in their chosen area and give them the freedom (and autonomy) to act.

Gameplays for Engagement
Dealing with competition if you can’t work with them:

  • Ambush: to attack with surprise, e.g. when competing with another open source offering we will drop at scale any proprietary features of the component into the open source offering whenever the competitor reaches near feature parity.
  • Fragmentation: exploiting pricing effects, constraints and co-opting to fragment a competitor’s market.
  • Misdirection: sending false signals to competitors or future competitors including investment focused on the wrong direction.
  • Reinforcing competitor inertia: identifying inertia within a competitor and forcing market changes that reinforce this.
  • Restriction of movement: limiting a competitor’s ability to adapt.
  • Sapping: opening up multiple fronts on a competitor to weaken their ability to react.
  • Tech Drops: creating a ‘follow me’ situation and dropping large technology changes onto the market.

The Art of Strategy: All Parts

Contents: A very short summary of each part
Introduction: What is strategy and why do you need it?

  1. Assessments: How to assess, prepare and shape
  2. Challenges: How to use and reduce inertia, entropy and friction
  3. Success: How to succeed together with stakeholders
  4. Setup: How to create resilience
  5. Momentum: How to use creativity, focus and timing
  6. Shaping: How to shape and avoid being shaped
  7. Engagement: How to engage using surprise
  8. Adaptations: How to adapt to shifting situations
  9. Movements: How to move to optimize momentum
  10. Landscape: How to approach difficult areas
  11. Situations: How to handle difficult situations
  12. Disruption: How to disrupt and avoid being disrupted
  13. Intelligence: How to use intelligence to create foreknowledge

Annex: Wardley Mapping Examples
Glossary: Explanation of key terms and symbols
Acknowledgements: Standing on the shoulders of giants
Sources: Where to learn more
Other reading and viewing formats

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

Wardley Mapping is provided courtesy of Simon Wardley (swardley) and licensed as Creative Commons Attribution-ShareAlike 4.0 International.



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Erik Schön

Erik Schön

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