If you ever have an opportunity to spend some quality time with a really successful entrepreneur or CEO, take it. Pay attention. Ask questions, and then listen to the way they respond. 

When I was first starting out as an entrepreneur, I made it a point to spend as much time as possible with people who had already done the very thing I was setting out to do. I'd pick their brains and take notes. And one thing I learned after meeting a lot of entrepreneurs is that the most successful ones are passionate about their business and can do everything involved extremely well. They're the total package: all-around players who can shoot, rebound, play defense, and handle the ball. That's what makes them hall-of-famers.

I've also met quite a few entrepreneurs and CEOs who got fired or ran their company into the ground. I tell some of these stories in full in my book, All In, but in short, these "less successful" entrepreneurs also share something in common. And they all share a fatal flaw no one tells them about. 

Why? Because they surround themselves with yes-men and women who won't give it to them straight.

And guess what? That's their fatal flaw.

Just about "less successful" top dog has this destructive tendency not to hire anybody smarter than them. Maybe it's an ego thing. Maybe they're control freaks. The truth is, it doesn't matter what the reason is--it's a huge mistake that ends up costing them more than it's worth.

As an entrepreneur, your goal in life should be to look around at the company you keep and truly  be able to say, "Wow, I can't believe I'm here with these great people doing this great thing." If you say that, your business will reap great rewards.

In order to build that sort of team, however, that means you have to do the opposite of what these "yes-men" CEOs and entrepreneurs do. 

You have to not be afraid to sugarcoat the feedback you give others, and you have to not encourage a culture that sugarcoats the feedback they feed you.

Too many CEOs surround themselves with people who don't challenge them enough, which immediately creates a culture of not saying what needs to be said. And since leadership starts at the top, what happens next is managers become afraid to give good feedback to the people they manage, and the people below them become afraid to give good feedback to the people they work with, and so on.

By not being direct, you do everyone a disservice. 

My advice to you is to do the opposite. Don't pretend everything is perfect, and don't hire people that make you feel smarter than you are. If you're the smartest person in the room, you're in the wrong room. If you, as a generalist and the leader of your company, possess more specialized knowledge over a given department than the person you hired to lead that department, you're in trouble.

The goal for an entrepreneur isn't to create a vacuum that makes you feel powerful and successful every time you walk into the office. The goal is to build a team of people who know how to challenge each other in the best ways possible. 

Just don't confuse being open and honest with being degrading and overly critical. 

In my 40 years of being in business, this is the one thing that it took me a long, long time to learn: people really do want to hear the truth.

It might not be the easiest kind of feedback to give. But it's the kind that will take you and your business the farthest.

Published on: Sep 4, 2018
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