A Student of Strategy

tl;dr: An exploration of the idea of strategy, some frameworks, and the lessons of the Peloponnesian War.

Like everyone else, I take pride in my efforts to think and act “strategically.”

But, over the past few months, I’ve started to ask myself the question of: “what is strategy, really?”

and, more importantly, am I really strategic?

Fundamentals of Understanding Strategy

My baseline for “thinking strategically” was how strategy fit into a framework. For me, I always liked Ben McConnell’s OGST (Objectives, Goals, Strategies, Tactics) to understand the role of strategy-in connecting tactics (what we are going to do) with objectives/goals (the things we want to achieve.) This one I learned about 13 years ago and it was a good start.

But that didn’t really answer the question for me. At a high level, sure, but it didn’t explain what the essence of a good strategy was.

Another piece of the puzzle came in an HBR article from 2008 that I have cited and shared hundreds of times, “Can You Say What Your Strategy Is?” That one showed a bit more about how to develop a strategy (in a very HBR-type of way), but the big takeaway for me was that “if your team doesn’t understand your strategy, you are going to have challenges.”

On a practical level, this was reinforced for me recently when I heard an Israeli general talk about his experiences. (For more, see: Lessons in Strategy and Leadership from an IDF General.)

Advanced Strategy Tools

While I had read the “classics” in terms of strategy (The Art of War and On War) and will probably do so again, there were two pieces of knowledge I discovered recently that really helped me a lot.

The first was the concept of a Wardley Map. The creator, Simon Wardley, uses a very simple approach to explaining the role of the strategist. He actually combines the lessons from The Art of War and On War (though he uses the OODA loop of John Boyd) to show a few things.

One of them was to help recognize that strategy involves visuals, not just text. It is critical to help people SEE the landscape in which they are operating and SEE the dependencies on which they are making decisions.

His maps were unlike anything I had encountered before and did wonders to helping me understand the layers of abstraction required to become a good strategist.

However, it was the book On Grand Strategy by John Lewis Gaddis that really accelerated my understanding of strategy as the alignment of vision with capabilities.

As a student of history, the examples he used resonated with me reinforced his point, which is something I covered in Days that World History Pivoted.

Interestingly enough, the example that Wardley used and one of the earliest that Gaddis used were the same, the History of the Peloponnesian War by Thucydides.

Learning Strategy from Ancient Greece

I spent a week in Greece this summer exploring the birthplace of democracy so the rivalry between Athens and Sparta was on my mind. That led my friend, Anand Thaker (he’s the co-founder of the MarTech Landscape that NSM copied for the blockchain space) to send me a tremendous gift, Pericles Of Athens And The Birth Of Democracy.

Pericles had many roles, one of which was strategos, which is the Greek term for “general” and which means “to lead that which is spread out.”

The author of the book, Donald Kagan, is a well-known historian. He’s thorough and articulate and when I read the following paragraph, it was like something magical clicked.

Brackets are mine.

“The emergence of a strong and independent Argos hostile to Sparta [note: change in Landscape] offered the Athenians a way to overcome the military inferiority that threatened the safety of Athens and seemed to prevent the victory of a naval power over Greece’s dominant power on lands [note: this is the goal]. By making alliances with Sparta’s Peloponnesian enemies, the Athenians could in effect fight the war in Sparta’s home territory [note: this is the strategy], keeping Athens safe [this is the objective].” (p.74)

and a few pages later, he introduces Pericles’ doctrine, something von Clausewitz would have appreciated (and probably did) as it provides guidelines for behaving in the “fog of war.”

“This expedition was characteristic of others Pericles would lead and plan: it was seaborne, without avoiding specific missions on land; it had limited goals and duration; and it was carried out with great regard for the safety of the men involved. [this is doctrine] ” (p. 83)

All of this is not meant to show that I am some kind of strategic genius. Far from it. What I think I am doing now is going back to look at moments of history and trying to deduce the strategy of those who were responsible for devising it.

By studying their thinking and using a framework and series of tools that can help, I hope that I can actually be as strategic as I like to think that I am.

I’m open to other book suggestions or ways to think about it if anyone has any.


A Student of Strategy was originally published in Data Driven Investor on Medium, where people are continuing the conversation by highlighting and responding to this story.