The Theory of Winning – Part One

Is there a theory of winning? Is there a way in which you can consistently stack the deck in your favour and win under any circumstances? History has proven that favourites don’t always come out on top – why not?

Is this simply a question of luck or is there a strategy to winning that can be applied in any circumstance?

I believe that there is.

I am going to break this article down into two or three parts because I want to ‘go deep’ into the explanation and find some examples from the military, business and sport that prove that this theory can be applied to any situation.

Manoeuvre warfare is the principle philosophy behind ‘how we fight’. If I can deconstruct, explain and teach it – you will be able to take this theory and apply it to any situation you find yourself in.

I also want to explain this philosophy to destroy a myth – that military leadership is about command and control and what works on the battlefield does not apply elsewhere. That is simply not true – and in my follow up I will talk about the importance of purpose, trust, and initiative to ‘make this work.’

Manoeuvre Warfare

Manoeuvre warfare is not new. Decentralised command, surprise and deception have been used efficiently for hundreds of years. Military leaders will have employed certain tactics that ‘stacked the deck in their favour’ and gave them a greater chance of winning. For the most part, they probably would have done this intuitively.

It would take a USAF Colonel called John Boyd to truly develop the concept and the principles of manoeuvre warfare and to shape the philosophy that we know today.

John Boyd was a fighter pilot who liked to win. He was a student of air combat and found that in the Korean War, USAF Pilots flying the inferior F-86 were consistently beating the Koreans in the Mig-15.

The Mig was superior in nearly all of the traditional ways of measuring a fighter aircraft. It was able to climb and accelerate faster and it had a better turning rate. The F-86 by contrast had a larger canopy and a hydraulic control system which meant it could transition from one manoeuvre to another faster – it was more agile.

The results didn’t make sense, US pilots shot down Koreans at a ratio of 10-1, a phenomenal achievement when you consider that they were flying what everyone regarded as an inferior plane.

Why was this happening? How could an inferior aircraft defeat one that was superior by nearly every measurement?

It would be easy to assume that US pilots were better trained, even braver perhaps but this wouldn’t explain the size of the ratio. Boyd continued to research this issue and developed a theory called ‘patterns of conflict’ that is the foundation of manoeuvre warfare.

Patterns of Conflict – The OODA Loop

Conflict can be seen as a series of decision-making cycles.

In the simplest format, we observe a threat, orientate ourselves to deal with it based on a mental model that is constructed from our experience, make a decision, and do something. This then starts again as our action changes the situation.


The faster that you can cycle through this loop, the more control you will exert on a given situation. The reason for this is that the faster you make decisions, the more control you have over the environment. By the time you opponent is starting to act, you have changed the environment by doing something to it.

This causes your opponent to panic as they loose control of the situation – and it is compounded the faster you cycle through the OODA Loop. A panicked opponent is one that will freeze and can therefore be defeated with little cost to you.

That’s the simplest explanation of the OODA Loop.

But it is actually far more complicated than that and Boyd would get frustrated if the cycle was simplified any further than the diagram below.


The reason for this is that the simple OODA gives you four things to consider – four steps. Naturally, it is easy to assume that each of the steps are equal in weighting. This is false – and the greatest misconception that surrounds this theory.

The Observation and Orientation phases of the loop are the most important. Making decisions and then acting upon them is comparatively quick and easy. The better you can observe and orientate yourself, the better the decisions and actions you can take leading to a better result.

Observation is about being able to see clearly. What is going on in front of you? What patterns are being created that are likely to continue.

In our world and on a grand scale these would be things like:

  • Baby boomers move into retirement age.
  • Internet speeds continue to get faster.
  • Technology continues to replace jobs.

The Orientation phase is how you position yourself to take advantage of what you’re observing. How do you set yourself up for success given the unfolding environment in front of you.

This is the most important part of the process because this is where your mental models exist. Your mental models are your automatic thinking pathways that you have developed. You can change them but you have to be conscious that they exist.

The best way I can describe a mental model is one that I was taught by my parents. When I was at school my parents taught me to work hard. Working hard leads to success is a mental model that exists within my head.

But if I am trying to execute a flawed business plan – it doesn’t make a difference how hard I work. This is an example of where the model is inappropriate for the situation.

Mental models and thinking patterns are developed and nurtured by the material you take onboard.

In the same way that a poor diet will lead to poor athletic performance, if you don’t read or take on material that shapes your thinking – you will limit your ability to orientate yourself for success.

Imagine you’re at a crossroads in your life and you want to some advice.

Sarah reads broadly. She has read over 10,000 books and watched less than an hour of reality TV. Mark doesn’t read. He relies on his experience to provide advice and spends his spare time watching reality TV.

Whose advice would you rather have?

I appreciate that the example is simplistic but it makes the point. Sarah is better able to orientate herself towards the future. She is proactive in her learning allowing her to build and break her mental models for the situations she faces. Mark is reliant on his experience which significantly limits his ability to orientate to his future challenges.

The point I am making here is that ‘self-development’ and lifelong learning have a compound interest effect which you are able to leverage against your future challenges. Ben Franklin talks about this with his ‘five-hour rule’.

Investing in your own learning is the most valuable daily habit you can create.


The OODA Loop is heavily weighted towards the Observe and Orientate phases. Never stop Orientating. The decisions and actions you take which decide the direction of your life are entirely dependent upon the quality and quantity of orientation you undertake.

I am now going to explain the theory in detail using historical examples from business, the military and sport to show how universally applicable the theory is.

In all of these cases, the person that was expected to win, the person with ‘the deck stacked in their favour’ – lost.

I hope you find this inspiring because if you can understand and apply this theory, you can turn the odds for whatever you do in your favour.

The F-86 vs Mig-15

Darwin was right. ‘It is not the strongest of the species that survive, nor the most intelligent, but the one most responsive to change.’

The first reason that the F-86 pilots were able to able to defeat the Mig-15 pilots is that they were able to observe the situation better. The F-86 had a bubble canopy whilst the Mig had an enclosed one. This ability to see what was going on meant that they could ‘observe’ the unfolding situation better.

The F-86 pilots were also able to transition between manoeuvres faster than their opponents, they were more agile so they were able to orientate themselves more effectively. These two advantages meant that they were able to get behind their opponents quicker and engage them with guns. When the Mig pilots realised what was happening, it caused them to panic which made it easier for the F-86 pilots to get into position for a kill shot.

Put simply, the ability to observe and orientate better than your opponent will lead you to make better decisions. Better decisions lead to wins.

Traditional aircraft design dictated that if it is faster and more powerful, can fly higher and further than its predecessor, it was ‘better’. You can imagine defence contractors selling the aircraft to the pentagon with all these new and improved features proving that it was better than the last model.

But no one was looking at the statistics and talking to the pilots. What the pilots wanted were ‘go-carts’. Small, highly agile aircraft with large canopies.

If they had these, they could get behind an enemy plane and shoot it down faster.

I don’t want to step away from the focus of this article but it is worth mentioning that a principle of Lean Manufacturing is to ‘find out what the customer wants, and give it to them.’ Talk to the end-user and ask them what they need. Don’t build products based on flawed assumptions or rubbish data.

The Rumble in the Jungle

Look for patterns of behaviour based on known strengths – how can you break your opponents will to fight?

When Muhammed Ali fought George Foreman in the Rumble in the Jungle he knew that George was a bigger, stronger hitter who had bullied many of his opponents into submission. This experience created a mental model in the minds of both fighters.

From Foreman’s perspective, it had always worked so why wouldn’t it in this fight?

Foreman’s game plan was to bludgeon Ali into submission. Ali was lighter, there was only going to be so much of this punishment that he could take.

Ali could rely on Foreman to come out swinging. This mental model had worked for him every time so far – why wouldn’t he use it again?

What Ali did was a brilliant example of exploiting the OODA Loop. Ali knew that Foreman would come out swinging. When he did, he rocked back on the ropes and absorbed the heavy punishment. After a few big hits, he asked Foreman ‘Is that all you’ve got?

This had probably never happened to Foreman before, no one would have asked him if ‘that’s all he’s got?!’ He kept going, throwing big punches and using the same tactic that had always worked for him. Ali waited and absorbed the beating – and then as Foreman was starting to tire, he started to fight back.

By this stage Foreman was exhausted and could barely defend himself. Ali won and the rest his history.

Did Ali use the OODA Loop consciously? Probably not.

But if we look at the build-up to the fight and Ali’s use of the ‘rope-a-dope’ strategy, you can see that he used the OODA Loop effectively to defeat an opponent who was the clear favourite.

Fischer vs. Spassky 

Use deception – get your opponent to build mental models based on flawed assumptions

I was listening to an episode of the Tim Ferriss show recently (Episode 219, c.26mins) when I heard a story that brought the OODA Loop to life in another very different context.

Bobby Fischer was an American chess prodigy who conducted the longest ‘con’ in sports history. A ‘con’ is when you deliberately play a game or behave in a way that makes you look weaker than you actually are.

Fischer always started his chess games by moving a pawn to king four.  He had a very limited opening repertoire and from the ages of 12 to 29 he used the same opening moves over and over again. I believe that there were two reasons for this.

Firstly, if you always start from a position of weakness, you get pretty good at fighting back. If you started every football game with a handicap of 1-0, you’d have to learn how to attack and score consistently. I believe Fischer was teaching himself to do this by creating his own position of weakness.

The second reason is that at this time, the Russians were dominant in Chess. In the build-up to the World Championships, Boris Spassky was supported by a group of Russian chess experts who studied Fisher’s game looking for patterns and ‘recipes’ that Spassky could learn to defeat.

Fischer probably knew that this was happening. By the time the match was played, the Russians and the Americans were engaged in the Cold War. Any opportunity to beat the other would have been seized upon as a way of proving the strength of their political systems. Fischer knew that the Russians would throw resources behind Spassky – it was a sensible assumption based on his observation of what the Russians had done in the past.

When the World Championship final came, Fischer used a completely different set of opening moves. He used moves that he’d never used before. The mental models that Spassky had built based on Fischer’s past performances were suddenly irrelevant.

This would be like a heavyweight boxer preparing to face an opponent that was right handed. He would have chosen his sparring partners and developed his training plan based on the fact that his opponent had an orthodox stance.

If his opponent steps into the ring and started fighting left-handed, suddenly, all the training and preparation would have felt inadequate.

Psychologically this is incredibly damaging to your opponent. They will slow down as they try to work out what is going on. This gets compounded as they realise what is going on and start to panic.

Fischer used deception to get his opponent to build ‘false models’ for how the game would progress. This strategy allowed him to seize the initiative from Spassky and put him in control of the situation.

Agassi vs. Becker

If you get inside the opponents OODA Loop – protect the position

There was a recent story about Boris Becker and Andre Agassi which proved that Agassi had got inside Becker’s decision-making cycle.

Between 1988 and 1989, the pair met on three occasions with Becker claiming all the wins. In the eleven meetings that followed, Becker only won one of them.

After they’d retired, Agassi revealed what he’d discovered. ‘When Boris serves, he sticks out his tongue. If it is in the left of his mouth, he serves down the tramlines. If it sticks out to the front, he will serve down the centre.’

Agassi was inside Becker’s OODA Loop.

He had discovered a ‘tell’ – a way of working out what someone is going to do before they do it. This meant that he could prepare himself to react faster than his opponent. He said that later on in his career, the biggest challenge he had was discretion and he had to deliberately let some points go in order to keep it a secret.

If you’ve found an advantage that puts you inside someone else decision-making cycle, you have to protect it.

If you don’t and use the information too much, your opponent will work it out and then change the way they play the game.

When the Allies broke the Enigma code, they sometimes had to let the Germans win. If they had over-used the information and the Germans had changed the code, they would have been back to square one.

If you have managed to create the conditions in which you are in control, protect the advantage. Keep yourself inside your opponents decision-making cycle.

The Public vs. Terrorist on the Train

Seize the Initiative, TAKE control of the situation. If one person demonstrates ‘the will to act, the will to take control’ – it will inspire othersOn 21 August 2015, a 25-year old Moroccan man Ayoub El Khazzani came out of the toilets on a train travelling from Amsterdam to Paris. He was armed with an AKM Assault Rifle and 270 rounds of ammunition. A passenger was heading to the toilet as the gunman exited and tried to restrain him, he was supported by another passenger who tried to get the weapon off the gunman. The second passenger was shot in the struggle. Soon after  a group of three Americans, two of them off-duty members of the US Armed Forces tackled and subdued the gunman.

Let’s review this incident through the lens of the OODA loop.
The gunman would have built a mental model for how the attack was going to play-out. He probably thought, ‘as soon as I start shooting, people will start running away and I will be able to chase them’. He was expecting to have the initiative and be in control of the situation.
As soon as he came out of that toilet, a member of the public tried to disarm him. It’s highly unlikely he would have expected this to happen. He was now being taken down a scenario that he had not planned for or expected. His mental model, his expectation of what was going to happen, had been completely disrupted.
Like the Mig pilots in the Korean war, when that happens, it becomes difficult to adjust because you are struggling to take control of a situation you expected to ‘own’. Your mental model and expectations are being shattered.
In this brief moment, the initiative was seized by other passengers who started to overpower the gunman.
This would have happened in fractions of a second but that is all it takes.
Netflix vs Blockbuster
Speed is relative – you just have to react faster than your opponents


This example is very different but it demonstrates the point that speed is relative. In the last example, the passengers had fractions of a second to go through the OODA cycle. In this example, the cycle is the same but perhaps played out over months or years.

Netflix was founded in 1997 by Reed Hastings and Marc Randolph. Initially, the company supplied DVDs by mail. At the time, Blockbuster was the dominant force in the video rental market. In 2002, it could have bought Netflix for as little as $50m but declined.

Netflix has gone from strength to strength whilst Blockbuster has failed.

They both started out with similar business models, Netflix were just better at adapting to the changing world. If you look at what they did through the lens of the OODA loop, you can deconstruct how they were able to change based on what they saw (observed) and how they orientated to it.

Youtube was founded in February 2005 and sold to Google in November 2006 for $1.65bn. The fact that one of the most dominant internet companies made that acquisition strongly suggested that some very clever people believed online videos were going to be popular over the next few years.

That deal was public knowledge – yet not everyone will have ‘observed’ it and considered ‘how does this affect my business?’

Internet speeds were increasing – what new opportunities would that bring?

By February 2007, Netflix had delivered its billionth DVD. It had been spectacularly successful but the Leadership will have accapted that past performance was not an indicator of future success. Netflix began to shift away from a very successful business model towards ‘on demand video streamed via the internet’. Netflix continued to grow as DVD sales fell from 2006-2011.

This is a great example of Orientating yourself towards the future. It was a reasonable assumption to make that internet speeds and therefore download speeds were only going to get faster – it is still a fair assumption. Netflix were able to spot the opportunity that this would bring and orientate themselves and their business model to take advantage of these changes. If they had planned to do this before Google bought Youtube, the acquisition would have reinforced their assumption.

Tempo and Speed

I have deliberately used examples from sport, the military and the world of business to make my points. The reason for this is that if you can find examples from a broad spectrum of environments, then the theory or principle can claim to be universal. It can be applied anywhere.

If you can cycle through the OODA loop faster than your opponent, you will start to change the situation. By the time your opponent catches up, they are already reacting to old information which makes their action inappropriate. As they start to realise what is going on, confusion and panic sets in. It becomes clear that they are going to lose and this breaks their will to fight.

Speed is important but it must not be confused with tempo.

Tempo is the ability to stop and start quickly. If you can speed up and slow down rapidly you will add a new dimension to your unpredictability. This makes it very difficult to take the initiative and seize control from you. It is disorientating.

It is hard to come up with a suitable example to explain this concept. The way I think of it is if you were running away from an attacker and could get into a crowded area, the ability to slow down and reduce your tempo would give you the opportunity to blend in with your surroundings. If your attacker doesn’t know where you are (can’t observe), you can orientate yourself and attack them from behind. Look at any of the Bourne films – his ability to strike and control tempo works pretty well for him

In the next article, I am going to talk about how you take the OODA Loop and apply it so you can make decisions faster. I will explain concepts that are directly applicable to business from the military, phrases such as ‘intent, main effort, purpose’ and the importance of decentralised command.

If you’ve enjoyed this article and found it useful, please share it.

You will be helping me to destroy the myth that military leadership is about ‘command and control’ and prove the fact that ex-servicemen can bring extraordinary value to an organisation because of their ability to think and solve problems in some of the most stressful and challenging circumstances.

Put simply – they’re experts at finding ways to win!


Arrange a Conversation 


Article by channel:

Read more articles tagged: Collaboration, Featured, Leadership, People Analytics

People & Change