Gary Vee: How to Tell Your Boss He’s Wrong

Do you hate your boss? You’re pretty sure they’re screwing stuff up, but no one wants to say anything because, well, they’re the boss, right? Except, as the situation progresses, giving feedback to your boss seems more and more like the right thing to do. So how do you tell your boss they’re wrong without jeopardizing your position or sounding like a jerk?

The first step really should be this: Check over and over that you are sure they are wrong. Giving feedback to your boss is one thing; calling him or her out incorrectly is something totally different. You really don’t want to get caught looking like an idiot in this type of situation. That can backfire majorly.

In the end, I truly believe this: If you’ve got a good boss, they will welcome performance feedback, and they will listen to you.

If your boss is good at being the boss, they will take your feedback and actually listen to what you have to say. Period. An enormous part of being the boss is about learning to be a better listener than speaker. You help the team out by being aware of what is going on at all times. What does that take? Listening.

The key to performance feedback is respectfully pointing out things you disagree with. If you go down that route, it’s a win-win situation. Think about it: If you give that information to the boss, and the boss agrees with you, you’ve won points and hopefully the situation will be dealt with. If they don’t and they completely disrespect your feedback, then now you know what kind of person you’re working for.

So, with those two points about talking to your boss in consideration, to me there is no risk in giving feedback to your boss. As long as you keep your cool and are diplomatic about the situation, the two outcomes we outlined above can only end well.

If you are putting your future into the leadership of an individual, don’t you want that person to be respectful of feedback? Or learning from their mistakes? This could be the question that determines if you are in the right place.

So if you have something to say, don’t hold back. Be respectful and approach it from calm ground. But don’t stick around if they won’t take you seriously. That’s not worth your time.


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Gary Vaynerchuk builds businesses. Fresh out of college he took his family wine business and grew it from a $3 million to a $60 million business in just five years. Now he runs VaynerMedia, one of the world's hottest digital agencies. Along the way he became a prolific angel investor and venture capitalist, investing in companies like Facebook, Twitter, Tumblr, Uber and Birchbox, before eventually co-founding VaynerRSE, a $25 million angel fund.

Gary also currently hosts The #AskGaryVee Show, a way of providing as much value as possible by taking questions about social media, entrepreneurship and family businesses, and giving his answers based on a lifetime of building successful, multimillion-dollar companies.

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