How do I become a great strategist?

Posted on June 1, 2020

To be a master strategist is like mastering any other discipline. The Nazi Troops lost the War in Russia because they were not equipped for winter warfare and froze. The details typically missed in casual histories is that the Nazi winter supplies never made it to the front; Cossack Cavalry using submachine guns and anti-tank rifles ate up the Nazi Supply lines ran by officers who assumed horses were obsolete in mechanized warfare; and all their supply chain security was based on defence from aircraft, infantry on foot, and trucks and tanks.

The Cossacks rightly knew that cavalry never goes hungry because a dead horse gives hundreds of pounds of fresh meat; cavalry can travel the same difficult terrain that infantry uses to escape vehicles; but much faster than on foot. Horses graze off the land and don’t need fuel trucks or roads. The Russian Military never talks about the use of horse cavalry for that very reason.

Unconventional strategies work great if you know what you are doing and can think sideways.

What is Strategy

A strategy is what a strategist does. Recognize the truth, assess limited resources, find the strength in those resources; and apply that strength against opportunities and weaknesses in whatever is between you and your desired outcome. Knowing that things are never going according to plan, anticipating that, and achieving optimal results despite internal politics, the fog of war, unintended consequences, mistakes, skilled opposition, and an unexpectedly hostile environment.

The strategy is knowing how to change the plan when things need to change.

In the end, most strategists specialize in a certain genre – business, politics, military, marketing, digital, investment; because learning the tricks in one setting is much easier and obtainable then combining a high IQ with an eidetic memory that has mastered several different careers to really be a master strategist in multiple settings.

Keep in mind – at the end of the day, you are stuck with yin and yang. Your actual ability will be defined by the challenges you face. Humans tend to play to the level of their opponents. A hero is defined by its villains.

Strategist Case study 101

When a more powerful nation with a huge army invaded the Kingdom that was Sun Tzu’s patron, Sun Tzu knew he could not fight them head-on or successfully defend his kingdom. So, he attacked the enemy’s homeland, sacked villages, attacked cities; forced his enemies to abandon their invasion to instead protect their homeland.

That is what a master strategist does. Create an opportunity where there is none. They use loss leaders or social movements to generate sales. They use black market criminals to supply food and fuel to soldiers fighting bad guys in faraway places because sometimes that’s the only way.

Other Skills for a strategist

Learn how to win by avoiding conflict.

Learn to win through win-win scenarios.

Get good at math, finance, and how to mathematically model stuff. These days that may mean learning Python or how to code if not being scary with spreadsheets. Operations research can give you an edge. The cold war was won by economics; thanks to RAND doing the math and Reagan listening to the math. He talked about Star Wars weapons, a thousand ship Navy, tricked the Soviets into bankrupting themselves – not a small feat considering Soviet Russia in the 1980s rivalled the largest producers of oil in the history of the earth.

Speaking of math. You have to study game theory, lots of it. Make game theory second nature; add that to complexity theory, psychology, and behavioural economics, with a good dose of modern military science; and you should be able to hit 90% at predicting what people will do, and manipulating them to your advantage; or at least, that’s the performance metric attributed to Bruce Bueno de Mesquita’s consultancy to the Pentagon back when it was new.

Go to the Association for Strategic Planning; Catch up on business trends in Agile Strategy, Scenario Planning, Competitive Intelligence, Innovation, Adaptability…

Get a Subscription to Stratfor – and see the difference in perspective when you get your news from the analysis of geopolitical intelligence experts that talk to people in languages other than English….

Books on strategy

To digress, read Erwin Rommel, Antoine-Henri Jomini, Carl von Clausewitz, Miyamoto Musashi. Micheal Porter, Max McKeown, Harvard Business Review, etc. All solid strategy resources.

Historian Ralph Zumbro has done some clever stuff. Study Hannibal, Alexander the Great and Belisarius if you have time.

Then read up Ford, Toyota, Steve Jobs, Ronald Reagan, JFK – Any disruptive historical figure or organization that dominated what they did. Read different cultures for different perspectives.

You have to learn science, history, political science, philosophy – to know what is possible. What science, engineering, and technology actually can and cannot do; and more importantly how they do, so you can improvise or disrupt them.

Study behavioural science, especially cognitive bias, decision making, deception science, habits and triggers, so you can predict how people will think, act, and react. That way one may learn to manipulate psychology to your advantage.

The “Japanese Art of War” – Great book by Thomas Cleary; that studies the culture of strategy in Japan. Most societies do not have strategic cultures. Cleary and Musashi are the only authors I’ve seen that show the offensive strategic value of Zen. But it works.

Read up on Colonel John Boyd USAF. John Boyd is a good example of a Master Strategist, that is very controversial because of who he was and how he did what he did. Everyone argues his theories, but nobody argues his results. And that guy read a book a day for decades, crazy workaholic.

Summary

So, if you want to be a master strategist, start trying things worthy of a master strategist. Create an opportunity where there is done, succeed at the impossible, and accept that when you succeed, depending on the challenge – few if any may recognize what you achieve because recognizable victory is a rare opportunity. Usually, master strategists end up in situations so complicated that nobody is sure what happened or who won.

Study the People that do it, study the history, the science, and practice the discipline until you get good at it. Hanging out with people who are good at it helps to. Find them. Learn from them.

Play strategy games (tabletop, board, video). Unconventional approaches among the easiest ways to kill a Dragon, Large Predator, or armies is to poison its food or water supply. If you know the Dragon feeds off a flock of sheep in the mountains; make it an offering of sheep full of broken glass, acid, poison, etc. Assuming the dragon is prone to swallowing things whole.