What I Took Away From: The Dichotomy of Leadership by Jocko Willink and Leif Babin

Ever since I lived in the US, I have a weird fascination with the military. I wanted to do military service in Germany too, but then they abolished it — so I didn’t. However, you don’t have to be in the military in order to learn from it. That’s what books are for, right?

Business and military strategy are fairly similar. „The Art of War“ by Sun Tzu is a timeless classic that every leader should read (doesn’t take long, I promise). The concepts apply to this day in everyday life. The work of authors like Stanley McChrystal (Team of Teams) and Jocko Willink is incredibly enlightening too, and I love reading their books. Which is precisely why I picked up „The Dichotomy of Leadership“.

I first learned about Jocko on the Tim Ferriss Podcast. His interview blew me away. This guy is the scariest human being available. Gets up every day between 3 and 4am (don’t trust me? Just follow his Instagram), is pure muscle mass and has the scariest voice you could possibly imagine. I definitely recommend the audiobook. 😉

So — what did I take away?

You can’t go to one extreme and still be a good leader, you always have to find the golden middle. I personally lend to lead more in a laissez-faire style, and sometimes too much so — which has the consequence that I don’t hold people accountable enough. I also know leaders which micro-manage hardcore — which has the consequence that people are pissed off and the leader himself doesn’t get anything done.

Therefore, find the middle. You still need to own up to everything you do (a concept Willink and Babin explain at length in their first book „Extreme Ownership“), but you cannot micro-manage your team members so hard that they can’t take extreme ownership anymore. Give people room to work on their own terms, but remember that in the end, it’s always up to you that the job gets done.

Hey hey hey, don’t get me wrong here — you’re not supposed to beat someone up. A concept that is reinforced in this book is „violence of action“. In a war, you don’t send like two soldiers somewhere, have them fire a round from their rifles and then retreat. No, you attack hard and violently.

The same is true in business. You should test your product, yes — but when it’s time to strike, strike hard. Expanding into a new market? Enter the market — but enter it violently. No „soft“ launch, but a hard one. Make sure everyone knows you’re there, and they don’t have another option but to buy your product.

This is another way of saying „pick your battles“. Where there are rules, people will try to disobey them. As a leader, you need to be aware of when it’s okay to let it slide and when it’s absolutely crucial that discipline is established. In my startup, we have a project management system, and sometimes people don’t enter all their tickets and tasks at the correct time. While that’s theoretically against the rules, I let it slide, because I know everyone’s busy and we’re preaching that you shouldn’t work overtime.

However, when I schedule an appointment in the calendar and the person I want to meet with simply doesn’t show up despite confirming the meeting, I can’t let that slide. In that situation, I had to hold the line and be very clear that that’s not going to happen again. So whenever you observe someone disobeying the rules, ask yourself: is it worth to hold the line here? Or can I let something slide in order to save my energy for the truly important battles?

Humbleness is one the biggest qualities of a leader. Chances are that your subordinates know what they’re doing, ideally they know it better than you. Wouldn’t it be rather stupid to tell them what they do, despite the fact that they’re better informed than you?

A true leader follows when he knows that his subordinate knows more, and leads when leading is necessary, for instance when it comes to strategic decisions, or in stressful situations. When everything goes according to plan, the leader doesn’t have to step in — but when shit hits the fan, his leadership ability is required.

Doesn’t matter whether you’re in military or project management — „no plan ever survives the first enemy contact“ (Helmut von Moltke, German field general). Plans are made in a vacuum, but life will always throw something at you that doesn’t go according to plan. If you don’t have a plan in the first place, you don’t know what you’re doing. But if you’re too rigid, you’ll end up like the Berlin airport (BER) and be delayed by ten years (my favorite example of bad, classical project management).

Leif Babin tells a story of where he tried to be overprepared: it was a 36 hour mission, so he had to pack accordingly. But what if it turned into a 72-hour mission? So he packed some water. What if my radio breaks? Better pack a backup one. What if I run out of ammo? Let’s pack a few more magazines. So he did all that, and his backpack was quite heavy. Well, guess what — he endangered the mission because he simply couldn’t run as fast with all his baggage. Be prepared, but don’t overprepare. When something extraordinarily happens, you’ll always be able to adapt.

I like to think the same way about packing for a trip: pack the essentials, but everything you might need, better leave at home. Chances are, you’re traveling to a place where other humans live. You’ll be able to buy an umbrella if you need one, you’ll also find sunscreen, lotion, and shampoo, and if it really gets that cold, sweatshirts usually aren’t that expensive either. You can always adapt.

Where should a leader stand in a military operation? The answer is: in the middle. If he’s too far up in the front, he’ll be right in the action, but won’t be able to see the bigger picture. If he stays back too far, he’ll have no idea what’s going on in the field. The same is true for management: if you’re in the weeds, it’s hard to see where the company is going in the long term; but if you’re focused too much on strategy, you might miss out on things that endanger your operations. I personally tend to be a little bit too much in the weeds, to do too much myself, so I sometimes simply forget where we’re headed in the long-term. I’m too busy solving short-term problems, and honestly, it really isn’t that important whether I take the plane at 7 or 8 am next week in the big picture. 😄

Leadership is tough. It’s probably the most difficult quality to achieve — which is why there are so few truly great leaders. Am I one of them? Hell no. Not yet. But this book helped me a lot to reflect on my leadership ability and I’m noticing myself using these concepts almost every day. And so can you!

If you want to learn more, just click here to buy the book itself. It is an affiliate link, so I may get something for it in return — if you’d rather support your local bookstore, feel free to buy it there. 🙂

Thanks for your time!

Much love,

Dominik

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Entrepreneur | Athlete | Writer. Reflecting on life’s challenges and figuring out ways to overcome them.