Chapter 11. The Art of War, Rebooted

Marcus Guest
6 min readMar 12, 2024

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“Everything that needs to be said has already been said. But since no one was listening, everything must be said again” ― André Gide

In the summer of 2007, the CEO[⁠1] of a UK software firm took the stage in Portland, Oregon (USA) to deliver a keynote address, then unexpectedly resigned. His speech, which was about the future of the computing industry, began with a bit of history. Computing, he explained, had once been the bright, shiny ‘new thing’ that everyone marvelled at. But due to supply and demand competition, it had evolved from a novelty used only by ‘leading edge’ organisations into becoming a widely understood product adopted by almost everyone. What, he asked, would come next?

He argued computing would follow the same path as electricity did. This too had once been a ‘technological wonder’ but was now a ‘utility service’ that people used without much thought — except when it’s unavailable or time to pay the bill. Subject to the same evolutionary pressures computing would also become a ‘utility service’, the CEO argued, and this would profoundly change not only the computing industry, but all industries that rely on computing.

Fig.22: Evolution from Supply and Demand Competition Pressure

http://conferences.oreillynet.com/presentations/os2007/os_wardley.pdf

Computer vendors were already aware of this. IBM, the leading vendor of the time, had spoken publicly[⁠2] in 2003 about “e-business on demand”, predicting that “computing power [would] becoming a ‘utility’, like electricity or water, which can be turned off an on as if from a tap”. Yet, while vendors saw this as the future of the industry, the tech CEO on stage was arguing that the future had already arrived and those clinging to the old business models would get left behind.

However, just before going on stage, the CEO received some devastating news. His organisation’s parent company had rejected his vision of capitalising on the shift towards ‘computing-as-a-utility like service’ (cloud computing) and leveraging the masses amount of data that could be used to build higher-order systems like machine learning. The parent company, under the influence of some very expensive management consultants, had decided that the future was 3D television and were going to make their technology investments there instead. Having seen a radically different future, the CEO, who could no longer announce the unorthodox moves he had developed to exploit that, resigned live on stage.

Following a period ‘in the wilderness’, the former CEO, Simon Wardley, joined Ubuntu, a small player in the cloud operating systems industry with less than 3% market share. Unlike his previous organisation, Ubuntu had a parent company who shared his vision of the future. Instead in ‘more of the same’ products they focused on capturing future real estate instead. In just 18 months, with half a million pounds of investment, they took 70% of a market that had been dominated by giants like Microsoft and Red Hat.

How did they do it?

Rather than trying to make detailed plans about a rapidly-changing future (the Western approach to strategy[⁠3]), Ubuntu focused on developing superior situational awareness and adaptiveness (the Eastern approach to strategy⁠[4]) instead. In this, they were guided by Wardley, who had been using Sun Tzu’s ‘Five Factors’ ever since he had picked up a copy[⁠5] the ‘Art of War’ and started to use it navigate a way through uncertain terrain. Tweaking the order and some some of the language Wardley was operating according to the ‘Strategy Cycle’:

Fig.23: Wardley’s Sun Tzu inspired ‘Strategy Cycle’

  1. Purpose — your moral imperative, describing the scope of what you do and why you do it, providing others with a reason to follow you.
  2. Landscape — a clear visualisation of the current environment you’re operating in.
  3. Climate — awareness of the external forces shaping this landscape, whether you want them to or not.
  4. Doctrine — implementing beneficial ways of operating, some of which appear to be universally useful.
  5. Leadership — context-specific choices about the ‘battle at hand’, since no two landscapes are identical.

To his horror, Wardley realised he’d been taking short-cuts. His strategy as a CEO had had been big on ‘Purpose’, but then jumped straight into ‘Leadership’ decisions of who must do what, by when. He’d had no sophisticated understanding of the ‘Landscape’ they were operating in, no understanding of how ‘Climate’ patterns were change it, and no concept of ‘Doctrine’ that the organisation should be operating by. He’d been a “bumbling and confused CEO⁠[6]” and that’s why he’d failed to get key stakeholders to buy into his vision.

Searching for answers he devoured business books, but found the same great leap everywhere — detailed descriptions of an organisation’s Purpose; then a huge leap to the Leadership decisions made that, in hindsight, were successful but provided no insight into why these decisions were made in the first place. There was nothing about how to understand the Landscape you’re competing in, or the Climate patterns changing it. It was all a ‘tyranny of tactics’ about who did what and when and the message was always the same — to be a great leader, copy what successful leaders did in the past. But what about all those leaders who had done the same thing but failed? Where were “the dogs that didn’t bark⁠[7]”?

Every situation has unique challenges and threats and each organisation different strengths and weaknesses — there is no one size fits all. So how does one create a strategy that will work for your organisation today?

Wardley then researched great historical leaders — generals, captains, explorers — and what he found shocked him. Every successful leader had maps to understand their Landscape — to identify favourable terrain or routes. They had an understanding of Climate patterns affecting their Landscapes — how overhead conditions changed the ground under-foot, or how trade winds enabled one to reach distant lands in different seasons. And all had a concept of Doctrine, or how to operate successfully by coordinating the actions of others to respond to changes and exploit opportunities in real-time. Knowingly or otherwise, it seemed that every successful leader was following Sun Tzu’s ‘Five Factors’ — all expect business leaders.

Business leaders are often fumbling in the dark, making decisions despite possessing little understanding of their wider situation, how it’s changing or where their options are. Success seems to rely on ‘strategic genius’ — but this provides few learnable insights for ambitious leaders.

Wardley set out to address this problem. The method he developed — that enabled Ubuntu steal the future from its rivals — is known as Wardley Mapping and today is helping companies like Amazon and Netflix, Shopify and AirBnB, as well as many others across multiple industries develop superior situational awareness. For, in times of uncertainty, the ability to look before your leap can be a key source of competitive advantage — ‘In the valley of the blind, the one-eyed man is king’.

“…understanding your landscape … is not a luxury for strategy, it is at the very core of it⁠[8]”.

Fig.23: Simon Showing Someone at Microsoft Wardley Mapping

Source: Simon Wardley

1 https://www.theregister.com/2007/07/27/wardley_zimki_fotango/ The article calls Wardley a COO whereas Wardley says he was CEO. I chose to accept Wardley’s definition of his role based on the idea that he probably knew it best.

2 https://www.nytimes.com/2003/01/26/technology/ibm-to-announce-push-on-grid-computing.html

3 See chapter eight — The Western Approach to Strategy.

4 See chapter nine — The Eastern Approach to Strategy.

5 Two copies actually as translations vary widely.

6 Which he details in his book, https://medium.com/wardleymaps/on-being-lost-2ef5f05eb1ec

7 The phrase comes from Arthur Conan Doyle’s story “Silver Blaze,” where a dog’s silence enabled Sherlock Holmes to deduce that a dog must have been familiar with the intruder, highlighting how sometimes what is not observed can be as significant as what is.

8 https://medium.com/wardleymaps/getting-started-yourself-e1a359b785a2

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Marcus Guest
Marcus Guest

Written by Marcus Guest

Govern the state by being straightforward; And wage war by being crafty. — Laozi, Tao Te Ching marcus@powermaps.net PowerMaps.net

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