How can leaders develop strategies that adapt to uncertainty and avoid the pitfalls of overconfidence?

In this episode, Rich sits down with Professor Sir Lawrence Freedman — Emeritus Professor of War Studies at King’s College London and one of the world’s leading scholars on strategy, international relations, and military history. Knighted for his contributions and the official historian of the Falklands Campaign, Sir Lawrence has authored seminal works including Strategy: A History, The Future of War, and The Evolution of Nuclear Strategy.

In this wide-ranging conversation, he shares insights on:

How strategy is more than a plan — and why it’s a continuous, iterative process

Why understanding your adversaries and allies is as important in business as in war

The dangers of hubris, overextension, and failing to listen to dissenting voices

How leaders can recognize when to adapt or reverse course without losing momentum

Sir Lawrence also offers timeless lessons for business leaders on reading context, anticipating friction, and practicing strategic empathy.

⏱ Time Stamps

(00:00) Deep Dive Interview with Sir Lawrence Freedman

(54:35) Practice Makes Profit

(56:23) League of Strategic Minds

(58:43) Winsights, Ideas for Advantage

🔑 Key Quotes

“Strategy is one of those things that you do without calling it strategy. So if people at any time are working out how to achieve what they want to achieve and looking at the means available, they're engaging in strategy.”

“It's easier to have a good strategy if you've got resources, much harder if you don't have resources, which is why, incidentally, a lot of the most ingenious strategic thinkers have been underdogs because they really needed to work at it.”

“The thing about strategy is it's a continual process. So I kind of talk about it as a sort of soap opera rather than a three-act play. You don't suddenly say, now I'm done.”

“If you look at why military strategy fails most, it's because of underestimation of your adversaries.”

“Most strategy, let's say 50% of strategy is defensive. I don't know how much that's taught in business schools, but that's the way in practice a lot of it's gonna work because you're just being caught out. So it's against the ability to read situations.”

🔄 Practice Makes Profit

Rich shares a practical exercise for conducting a meeting audit — helping leaders reclaim time and improve organizational efficiency by aligning meetings with strategic purpose.

🧠 League of Strategic Minds

Listener Question:
What are the keys to leading a truly strategic meeting?

Rich outlines the importance of clear agendas, pre-work, interactive dialogue, and actionable takeaways to transform standard meetings into value-creating sessions.

💡 Winsight: Idea for Advantage

Michael Porter reminds us:

“It’s healthy for people to disagree, but there comes a time when discussion ends. Strategy is about picking a direction and getting everybody really excited about it.”