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Leadership

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Leadership Debt

When you ask people to go above and beyond, and they do it, you go into debt. I am talking about those circumstances when you ask people to work hard, really hard. Those happen at Startups, and occasionally they happen at big companies too—those do-or-die moments when everything is

Leadership Debt
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The number one mistake leaders make.

The biggest mistake a leader can make is to not fight enough for their people. In all of the largest companies, promotion time is a time of in-fighting. It is contentious at Amazon, Facebook, and every highly competitive place. A promotion cycle is when managers literally shout at each other

The number one mistake leaders make.
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Perfect Timing Feels Like I’m too Late.

I graduated with my undergraduate degree over a year late. I almost didn't graduate because I worked full-time in a restaurant. I needed money to help my immigrant family and to pay for that college degree I almost didn't graduate from. I started my career late at 26 too. I

Perfect Timing Feels Like I’m too Late.
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We can't stop people from messing up.

We cannot stop people from messing up, even the people we care about. We can write it down. Spell it out. Shout it until our lungs don't work, but people will still do what they want to even in situations where it so obviously going to be a mistake. Even

We can't stop people 
from messing up.
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Why do Groups Haze?

Gangs have initiations; potential Gang members have to go through crazy things like getting beaten by the entire Gang. Fraternities and Sororities make recruits go through punishments so bad that law enforcement and schools have had to crackdown. Every tribe has some hazing that they put new members through, even

Why do Groups Haze?
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The Paradox of Leadership

The paradox of leadership is that to be great leaders, it's best to have to have done the thing we lead people to do. But doing is always a different skill set than leading people. Yet, although those skills are different, I argue that the best leaders have been in

The Paradox of Leadership
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A lesson on leadership: One hand washes the other.

Where I grew up in The Bronx, in the Italian restaurant that I used to busboy in, I would hear the mafia guys who ate there say, "Don't mention it; one hand washes the other." I was young back then; I started busing tables at 14. But even I could

A lesson on leadership: One hand washes the other.
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When to remove a bad apple

Letting go of one of my best-performing engineers was by far one of the hardest things I’ve had to do as a leader. I still think if I could’ve gotten a different outcome. Leading people is hard because people are leaky abstractions. In software engineering, a leaky abstraction

When to remove a bad apple
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How to lead with no backup

It is easy to lead others to keep going when we know there is backup coming. But how can we lead people when there is no backup, no hiring, and no more help? Situations where money has run dry, or there was never enough, are more challenging. But these situations

How to lead with no backup
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How to build a great engineering team from the ground up

When building a house, if you want to develop one that will last, you will start with the foundation and make sure that's done right. After the foundation, you build the walls, then the roof, and then finally spend a long time inside and outside, adding the finishing touches. You

How to build a great engineering team from the ground up