Millennials get a bad rap sometimes. Entitled is probably the adjective that gets lobbed at them the most.

I have a handful of twenty-somethings who work for me, and I've seen both sides. Some arrive with an amazing set of skills. They're hard working. Balanced and patient.

Others fit the stereotype. Entitled.

I love when the first group shows up. The second group tests me as a leader. At times, I feel ill-equipped to make a difference with them. But shying away simply isn't an option.

They all want to get ahead. This second group wants it quickly--sometimes too quickly, in my opinion. Sometimes too quickly for their own good. This is where we get to a nasty three-letter word: Ego. Ego always drives entitlement.

But here's the good news. There is a cure for entitlement: Humility. Humility literally cures entitlement. It's always a hard concept to explain. It's elusive. "Be humble."

Yet, I firmly believe humility is the number one trait young leaders must master in order to develop into great leaders. A lack of humility is also the top reason young leaders don't advance as quickly as they'd like. 

But how do you teach humility? It's a tough question with no great answers. I try and constantly lift it up as a must-have. I try and lead by example. I over-communicate its importance.

This email was one I sent to a young employee several years ago. I have since re-used it many times. It's meant to state the clear case for humility and give a simple checklist to follow.

Here's the email.


I wanted to capture my thoughts on our latest favorite topic--Eric's life and career--so there is zero ambiguity on where we are. Specifically, I want to share some things on where I think you are and what you need to do to get to the next level. We've talked about these, but sometimes a certain clarity comes from writing and reading.

I think you do many things well. You're a smart guy. You have solid insights. You know our space and product VERY well. You're motivated. I'm going to spend less time on that list in this email. But, it's part of your story.

This next part is meant to be a sledgehammer on what I think you need to work on, improve on, or look at differently in order to get where you want to get in your career. Ergo--this is meant to be harsh.

HUMILITY. You need to genuinely approach your work life (maybe your life) with much more humility. This needs to be an instinct. It needs to be the lens with which you view your interactions with people. Every mistake you make should be a viewed as a win, and there should be lots of them. That would mean (1) you are pushing yourself to the limits of your capabilities (2) you realize that mistakes are OPPORTUNITIES to show humility with others around you. People do not relate to or follow arrogance. Your current default mode when you make a mistake is defensive. You work very hard to rationalize or explain why something went wrong. Usually, that comes down to "it's not my fault." Today, this is your instinct. Humility needs to become your instinct. Humility is a REQUIRED trait for leaders. Your handling of the new reps has been a real window into where you are with this. You have done some good things in this role, and that's why you have this opportunity. But you're not ready to be titled the leader of that group. I would be setting you up to fail.

How does one become humble? Well, I'm not really sure. I think for some it simply takes time and a witness to what kinds of people really succeed in the world. Practically, if you follow these ideas it's a start:

  1. Take ANY opportunity to own mistakes, screw ups and shortfalls

  2. Take ANY opportunity to give away credit for wins to other people

  3. Ask for help from a genuine position of shortfall (I have no idea what I am doing here, could you help me with...)

  4. Learn the art of issuing a genuine apology

  5. View failure as a necessary step for growth, not an indication of weakness

  6. Approach your work life with some perspective on where you are in your career and how much you still have to learn

Eric, humility is the key to your development as a leader. Make it a priority and see what happens. Have a good weekend.


Humility is a tough, but essential concept to understand for young leaders. But this is also for the seasoned leaders out there. Don't shy away. Take it on. Be firm.

And of course, be humble.