Good Leadership Builds Leverage

You are messing with AND disempowering the people that work for you AND you probably don’t even know it.

A short leadership story, and a lesson you can apply today.

I worked for some incredible leaders (often prior military) early in my career.

Almost everything about my leadership style comes from them.

Lots of Marines, Rangers, those types of dudes.

One day, I came strolling into the consulate in my finest dark blue bespoke suit, mahogany Allen Edmonds’, and tastefully checkered silk pocket square.

Full of the arrogance/confidence that only a twenty something with a few wins under their belt could have.

As I made myself a cup of coffee, my (prior Marine) big boss came in.

“Morning sir, how’s it going?” I said, eager to get a passing word of encouragement.

“Good, good.”

“Jon, I noticed you decided not to wear a tie today. “

“We’ve got that big meeting today that you are briefing at with (even bigger boss)”

“Any reason?”

“No sir”

“Ok - well , I’m sure my deputy will have something to say to you about that.”

He didn’t say another word, and walked back to his office.

10 seconds later his deputy (#2) walks out to my desk.

“Jon, what the fuck?

Go home and get a tie on you jabroni.

Don’t be an idiot please”.

End of Story.

Did you miss it?

The incredible discipline my big boss had?

Of course he could have said “Jon go get a tie on” - he was the big boss!

But that would have been incredibly disempowering to his deputy, who was in charge of me.

It also would’ve messed with the authority of the deputy in my eyes!

Instead, he took a moment to be deliberate about his leadership style, and worked his way through his deputy, thereby empowering his deputy and strengthening his deputies role, in the eyes of his team.

What incredible discipline!

What’s an example of how you might be messing this up in your company?

A common example might be the CEO answering direct slack messages from people that don’t report to them - without looping in that person’s supervisor.

Slack Message:

“ Hey Jon, do you have a copy of the policy for how much vacation I can take?”

What’s the best response if you get a direct message from someone in a situation like this?

Even if it could take you two seconds to respond ….don’t.

Reach out to their boss and say something to the effect of “hey Bob reached out to me. He wants to confirm how much vacation he can take this year - can you let him know? “

Of course you know the answer to that question… you’re the boss!

But do you want to set the precedent you’re the person to ask vacation questions to?

Here is the alternative.

You decide to bypass your team and handle things directly.

Sure, it feels efficient in the moment, but what’s the fallout?

First, your team feel sidelined, like benchwarmers watching the game rather than playing in it.

This isn’t just about hurt feelings; it’s about stunting their growth as leaders.

They don’t get to flex their problem-solving muscles or build rapport with their team.

And the team?

They start seeing their boss as just middlemen, not real decision-makers.

Before you know it, your leaders are mere figureheads, and your team’s knocking directly on your door for everything.

You’ve accidentally built a bottleneck at your own desk – congrats, you’re now the go-to guy for vacation policies and printer jams.

This is one of the most important parts to develop the leadership skills and empower the folks in your organization around you.

I see people make this mistake all the time and then in the next breath wonder why their leaders aren’t acting with individual initiative.

Also, I did a four part series with my buddy Peter - about hiring a global talent assistant, and using them effectively.

I think it was pretty good.

Check it out.

Part 1:

Part 2

Part 3

Part 4

Yallah Habibi,

Jon

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Passage of the Week:

A few passages from “When Nietzsche Wept” by Irwin Yalom (one of my favorite authors)

• “He had never encountered a patient who did not secretly enjoy a microscopic examination of his life. And the greater the power of magnification, the more the patient enjoyed it. The joy of being observed ran so deep that Breuer believed the real pain of old age, bereavement, outliving one’s friends, was the absence of scrutiny—the horror of living an unobserved life.”

• “Inquiry and science start with disbelief. Yet disbelief is inherently stressful! Only the strong can tolerate it. Do you know what the real question for a thinker is?” He did not pause for an answer. “The real question is: How much truth can I stand? It is no occupation for those of your patients who wish to eliminate stress, to live the tranquil life.”

• “Ordinarily, leavetaking is accompanied by denials of the permanence of the event: people say, ‘Auf Wiedersehen’—until we meet again. They are quick to plan for reunions and then, even more quickly, forget their resolutions. I am not one of those. I prefer the truth—which is that we shall almost certainly not meet again. I shall probably never return to Vienna, and I doubt you will ever be in such want of a patient like me as to track me down in Italy.”