How your ‘cool’ boss is killing your career

Your chummy supervisor probably won’t be candid with you about your performance. Worse, he or she probably isn’t well regarded by the higher-ups, so any ‘influence’ in promoting you is minimal.


My wife and I have saying in our house: “We never want to be the ‘cool’ parent.”

You know why? “Cool” parents are the ones who let their kids do things they shouldn’t be doing as kids.

It’s not my job as a parent to get my kids to like me; it’s my job to raise responsible adults who do better for their family and the world in general. That means we say “no” a lot.

“No, you can’t go to the movies at midnight. Yes, I’m aware the Browns allow this; they also allow their 17-year-old son’s girlfriend to sleep over, and the teenagers to drink .”

I would rather you shoot me in the head.

Being a boss is like being a parent

You know what’s funny? I don’t think my kids hate me. (Kids, please don’t comment on this post.) Kids like having boundaries. They don’t tell you they like this, but when they have boundaries, they act like better people. If you leave them without boundaries, you end up with Lord of the Flies.

I’m not saying that being a leader/boss/supervisor is like being a parent. OK, yes I am. It’s very much like being a parent.

Everyone wants to be the “cool” boss when they first start out in a managerial role. It’s very normal to think this and go down that path.

What you find out quickly is that employees, much like children, don’t perform as well without consistency. Things at work are going great, you’re the “cool” boss, and all of sudden, times get hard, you lose a big client, you have to make tough decisions, and your employees lose their minds.

This happens because you begin acting in a way you never have. You begin hearing things like: “You used to be so cool,” and, “You seem stressed all the time.” These are signs that your subordinates think you’re friends.

‘Cool’ bosses won’t be straight with you

Let me tell you a little secret: Friends don’t fire friends. You are not friends with your subordinates. You might be friendly, but that doesn’t make you friends.

“Cool” bosses who believe they are friends with you also rarely tell you the truth about your performance. Why? Because they don’t want to hurt a friend’s feelings. They hint at it, they run all around the bush, but they’ll never really tell you what’s holding back your career.

Here’s an example: “So, Tim, tell me—what does it look like for a promotion?” (I’ll be Tim, the Cool Boss.) “Well Mary, you know I back you 100 percent. If anyone deserves it, it’s you, but it’s not my call. I’m sure you’ll get it.” No, she won’t.

A “cool” boss can ruin your career faster than almost anything else in the corporate world.

Though you might think the cool boss is great, the reality is that your executive team knows better. They know this person lacks what it takes to move the organization forward, and is probably stuck in middle-management for life. A “cool” boss lacks the credibility needed to influence decision-makers. This makes it very hard for your ideas to be seen and heard at an organizational level.

3 ways cool bosses kill your career

So, what are the three ways your “cool” boss is killing your career?

  1. They aren’t helping you get the most out of your talent.
  2. They won’t be honest with you about what you need to change.
  3. They don’t have the influence to move your career forward.

How does it sound being the “cool” boss now?

Tim Sackett is executive vice president of HRU Technical Resources, a contingent staffing firm in Lansing, Mich. This article was originally published on his blog, The Tim Sackett Project.

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