Three signs of a cool boss

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• December 5, 2007
• By Ryan Healy
• No Comments

This post was originally posted at Employee Evolution

It’s not easy to be a good boss. Managers are responsible for nearly unattainable results, multiple daily meetings and managing their employees.

With all of this responsibility it’s hard to blame a manager for not being the world’s best boss because; after all, results move you up the ladder. I can see why the actual managing part is not always priority number one.

But happy employees are productive employees. The most successful managers understand this and put their people before everything. Here are three signs of a cool boss, from a Gen-Y perspective.

They take an interest in your career

Sure, it makes total sense for a manager to take an interest in your career within the company, but a great manager takes an interest in your ENTIRE career.

The best conversation I had with a co-worker at IBM was at lunch one afternoon with my boss. He asked me point blank:

“Do you see yourself working as a consultant for a while?”

For some strange reason, I felt totally comfortable replying:

“Actually, I really don’t think so. My goal is to start my own company.”

Then he replied and told me that he had a feeling I wanted to be an entrepreneur because every time I spoke about my brother or my friends running companies, I was really excited. We discussed the pros and cons of entrepreneurship versus corporate life, and the best age to start a company. It was great.

This was important for two reasons. For one, my boss actually listened to what I had to say in our past conversations. Secondly, he did not try to convince me to stay in the consulting field or with the company. He took an interest in my ENTIRE career, and I have great respect for him because of that.

They ask for feedback

I recently spoke with Globoforce CEO, Eric Mosley. Globoforce is a forward thinking company that provides online employee recognition programs. For example, if an employee goes above and beyond at work, a co-worker or manager will send them a “thank you” award. The award may be a gift certificate or any number of small gifts.

One of the best parts of these recognition programs is that they provide a means for two-way feedback. Not only can my boss thank me for putting together a great PowerPoint presentation, but I can thank her for taking the time to help train me in SAP.

This two-way feedback is great, but a cool boss will take it a step further and provide me with consistent feedback, both good and bad. And, most importantly, she will ask for feedback. After all, who better to analyze your management skills than the people you manage?

They are your friend, at work

This may be a uniquely millennial trait, but I believe your boss should be your friend, at work. A great boss will do whatever he can to find common ground with his employees. When you’re trapped in an office together for 8-plus hours a day, it’s important to take breaks and just “shoot the shit” with your boss every once in a while.

I used to wander over to my boss’s office and poke fun at his favorite football team, the Steelers, for losing a big game last weekend. He would then make a crack about Penn State being terrible or the Patriots choking in the playoffs the year before. These conversations were really important for our work relationship.

No one wants all business, all the time. A cool boss understands this and finds common ground with his employees. That being said, I’ve come to realize that it’s dangerous to cross boundaries and become close friends outside of work. A good boss understands this and makes a point to keep the friendship at work.

I’m sure there are a ton of different criteria that can make someone a cool boss, but these are my top three. What do you guys look for in a boss?

Ryan Healy is the COO/Co-Founder of Brazen Careerist and regularly writes and speaks on all things Gen Y, Careers and Entrepreneurship‬

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