3 Ways Your ‘Cool’ Boss Is Killing Your Career

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 you 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 got the movies at midnight. Yes, I’m aware the Brown’s 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.

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. Okay, 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 this 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, all of sudden times get hard, you lose a big client, and 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 use to be so cool.”; “You seem stressed all the time.”  These are signs that your subordinates think your friends.  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 ‘friends’ feelings.  They hint at it, they run all around the bush, but they’ll never really tell you what you’re doing that is holding you back in your career path.  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%!  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 any single thing you run into in the corporate world.  While you might think the cool boss is great, the reality is your executive team knows.  They know this person lacks what it takes to move the organization forward, so they are 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.

So, what are the 3 Ways you ‘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 and 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?

4 thoughts on “3 Ways Your ‘Cool’ Boss Is Killing Your Career

  1. So true….but also think it’s crucial to quickly follow that idea with the notion that fairness, realistic goal setting and consistency is paramount to gaining respect and great work from a team. Don’t be the “cool” boss, but don’t be such a pain to them that the team feels that the rug can be pulled out from under them either. Cut the weeds down for them, get them the tools they need, support their strong efforts….fairness and support coupled with diligent support for their efforts to achieve the goals YOU set will make you the GREAT boss, not the “cool” boss. That’s when winning happens and productivity has a chance to be “maxed out.”

    Re: Bryan’s comment about a “fun” place to work. I could be wrong, but I don’t think an employee truly expects to work at a FUN place. They DO expect to work at a place that respects their efforts and helps them achieve greatness. They have their real fun at home with their own interests, family and friends.

  2. Interesting, true, but how do you contrast this with common direction for managers and “bosses” to make work “fun” for their people?

  3. Tim,

    This is so true! Love the perspective and I agree with you 100%. My parents weren’t the cool parents as I grew up, but now I know why they did the things (and said ‘no’) they did. Great article!

    Keep up the good work.

    Kirk Baumann

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