Generally Speaking: Three Leadership Lessons of David Petraeus

Jeff Cunningham
Once Upon A Terroir
3 min readAug 28, 2023

“There’s a little bit of the stubborn Dutchman in me, taking after my old Dutch sea captain father. He was fairly relentless.”

Interviewing General David Petraeus

In a wide-ranging, candid interview with America’s most decorated war hero, General David Petraeus, we discussed the pressures he faced in Iraq, Afghanistan, and the Oval Office. Whether you are headed to the battlefield or run a startup in your garage, the leadership lessons he imparts are all too relevant.

1. Set Boundaries

JC: You and President Obama had a frank discussion of how you saw your role in Afghanistan?

DP: I felt it was essential for him to know who he was getting. In the Oval Office I said, “Mr. President, you should understand that I will provide my best professional military advice based on the facts on the ground and the mission you’ve given us and informed by the issues with which you have to deal uniquely — I’ll be aware of those, but facts on the ground will determine my advice. If those facts are unchanged, so my advice, too, will be unchanged.”

JC: How did Obama react?

DP: That was an interesting, tense moment.

2. Big Ideas

JC: Did you ever stop to think about your decision making style?

DP: To be truly effective, everyone should take the time to get the big ideas, then how to communicate them effectively to the breadth and depth of the organization, and closely oversee their implementation.

JC: How did you approach your role in the dismal state of affairs in Iraq?

DP: The first thing I would say about the success in a region, I’d like to think that I had devoted a great deal of study to understanding the human terrain in Iraq. Then, I spent a great deal of time getting the big ideas right. So I was aware that my first thoughts may need to be refined, revised, shot and left by the side of the road, and I might have to do it all over again and again and again.”

JC: How did you get your troops to follow the spirit of your commands?

DP: It takes a great, great team and everybody embracing the idea. Finally, there’s a little bit of the stubborn Dutchman in me, taking after my old Dutch sea captain father. It took a high degree of determination.

3. Pressure Points

JC: Was the pressure you faced relentless?

DP: Part of the problem, and this was very true in Iraq, but it’s also true in the C suite — you deal with intractable problems day in, day out, and you have few peers that really understand your pressures.

I can recall, after a tough, tough stretch, things were finally starting to turn, but there were political battles, the prime minister had issues, the members of the Parliament were causing all sorts of distractions.

JC: How did you handle that?

DP: There was a moment when I just called up the Chairman of the Joint Chiefs and said: ‘Hey, Admiral. I just want you to know this is not the easiest thing in the world.’ I just felt that somebody needs to know.

That’s the final challenge, as they say, that’s the loneliness of command.

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