Humility in Leadership: Know When to Let Others Lead

This article is an excerpt from the Shortform book guide to "The Dichotomy of Leadership" by Jocko Willink and Leif Babin. Shortform has the world's best summaries and analyses of books you should be reading.

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What is the importance of humility in leadership? How do you strike a balance between trust in others and self-reliance?

Being a leader doesn’t always mean telling people what to do—often, other team members are better equipped than you to make the right decisions. However, if you’re too reliant on others and lack confidence in your leadership, you may end up following others’ lead in situations where you know better.

Here’s how to strike a balance between trust in others and confidence in your ideas.

Know When to Step Back

Willink and Babin explain that part of radical accountability is basing your plans on the best ideas, no matter who came up with them. Often, this means trusting someone with specialized experience more than your intuition, even if you technically outrank them.

According to Willink and Babin, some leaders cling to their ideas because they want to appear confident to their team. This has the opposite effect: Overconfidence in your decisions will only cause your team to doubt you more. If, instead, you show humility in your leadership by willingly adopting a plan from one of your subordinates, your team will see that you honestly want to succeed and have their best interests at heart.

Willink and Babin argue that you should not only defer to the leaders serving under you but also to the leader in charge of you: your boss. Every time you fulfill your boss’s expectations without complaint, you earn their trust and make them more likely to respect your opinion in the future. This is extremely helpful for the mission—an adversarial relationship with your boss makes everything harder. For this reason, even if you think an order from above is pointless or unnecessary, execute it as if it were your idea.

The App That Allows Anyone to Lead

Like Willink and Babin, hedge fund manager Ray Dalio built his organization on the principle that good ideas can come from anywhere. In Principles, he describes designing his investment firm to be an “idea meritocracy” in which good ideas from anyone in the company can influence decisions at every level.

One way Dalio promotes this idea meritocracy is with an app he calls the “Dot Collector.” Dalio explains how this app works in a TED Talk: During a meeting, team members use their personal devices to give real-time feedback on whoever is presenting, adding comments and rating them on a scale from one to ten for a number of attributes. Anyone, even the newest hire in the meeting, can criticize anyone presenting ideas, even the CEO. Bridgewater’s leaders don’t just allow this feedback, they encourage it—it’s practically an obligation. By allowing anyone to question their decisions at any time via the Dot Collector, leaders at Bridgewater prove that they’re open-minded and earn the team’s trust.

Dalio’s company only hires leaders that fit the idea meritocracy culture—that is, those who can handle constant honest feedback. While Willink and Babin argue that you should mostly avoid criticizing your superiors to maintain a positive, productive relationship with them, Dalio proves that it’s possible to create an organization in which mutual criticism doesn’t strain relationships but strengthens them.

Know When to Fight for Your Ideas

On the other side of the dichotomy, you face different problems when you become too deferential to the plans of others. If you’re positive that following someone else’s plan will lead to disaster, you have a duty to fight for your ideas. Willink and Babin argue that sometimes, you’ll know something your boss doesn’t and realize that following their orders would be a serious mistake. Alternatively, several team members below you may push back against a plan that you know is best. If you cave to external pressure and accept a bad plan because others want you to (perhaps because you know no one will blame you when the plan fails), you’re not accepting radical accountability.

(Shortform note: Crucial Conversations offers tips on how best to challenge someone else’s plans. First, create a comfortable space for conflict to take place: Ensure that both of you feel respected and agree on the mutual purpose you’re trying to achieve. Then, begin your discussion by identifying the facts you both agree on before investigating where your views differ. This helps avoid a common pitfall of high-stakes debate: People often end up arguing furiously over minute details without realizing that they mostly agree. Not only does this waste time, but it also makes debaters feel like enemies instead of teammates.)

Similarly, encourage team members under you to fight for the ideas they believe in. Willink and Babin note that your team will likely be hesitant to push back when you give them orders, so specifically instruct them to do so for the greatest chance to find the best plan.(Shortform note: The Practice of Adaptive Leadership makes the case that leaders should pay special attention to contrarian team members who question leadership decisions at every opportunity. The authors claim that most organizations silence or fire these contrarians, as they’re often unpleasant to work with. However, if you instead encourage them to speak up, you can tap into an endless source of honest feedback.)

Humility in Leadership: Know When to Let Others Lead

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Darya Sinusoid

Darya’s love for reading started with fantasy novels (The LOTR trilogy is still her all-time-favorite). Growing up, however, she found herself transitioning to non-fiction, psychological, and self-help books. She has a degree in Psychology and a deep passion for the subject. She likes reading research-informed books that distill the workings of the human brain/mind/consciousness and thinking of ways to apply the insights to her own life. Some of her favorites include Thinking, Fast and Slow, How We Decide, and The Wisdom of the Enneagram.

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