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What 10 Years Have Taught Me About Bosses

When I got my first job out of college, I admit that I had a distorted view of my boss’s role in my work life. After all, I had just spent the last 4 years with college professors. They made fantastic bosses! They let me schedule time during their office hours to get help on assignments. If I didn’t like an assignment, I could argue with them about it--and they listened! If I was displeased with a particular grade, I could occasionally talk my way into a slightly better grade. I didn’t realize how good I had it.

Fast forward to my first real job, and my boss was nothing like my old professors. There were no office hours with which I could use to get help. Complaining and arguing about assignments got me nowhere. And I had no grades to help gauge how I was doing. Clearly, I wasn't in the classroom anymore.

Call it lack of experience. Call it naiveté. Call it youth. Whatever the reason, I had failed to discern the fundamental difference between college and work: in college, I was paying my professor to help me be successful. In the workplace, I was being paid to help my boss be successful. Internalizing that difference has been a game-changer for me.

When it comes to job satisfaction and career progression, the relationship you have with your boss is the most important relationship you have at work. It trumps the relationship you have with peers, subordinates, employees in other departments, and anyone else you associate with in the office. If your employee-boss relationship is weak, it can be draining, stressful, and downright miserable enough to make you call a headhunter. On the other hand, if it is strong, it can be a fulfilling and invigorating—oh, and lucrative—experience.

Regardless of the type of boss you have, I have learned over the last 10 years in the workforce that there are some simple ways to keep that boss happy, and thus keep your career moving forward:

1. Preempt Surprises: “I hate surprises,” is one of the most familiar phrases echoed in corporate halls. Why does your manager hate surprises? Because surprises make him or her feel uninformed, unprepared and vulnerable. So try to give your boss a heads up when something important happens. Remember, they have to keep their bosses happy, too.

2. Deliver Bad News Quickly: Bad news is unavoidable. Don’t sweep it under the carpet and pray for it to go away, because it won’t. The last time I tried to hide a mistake from my boss, she found out about it on Twitter from an upset customer. Oops.

Not delivering bad news to your boss quickly is like letting a wound fester and spread until the infection becomes life-threatening. Telling your boss about a problem immediately is like applying alcohol to a new wound. It stings a little bit at first, but allows the healing process the begin immediately.

3. Come with Recommendations: No boss likes to have a problem dropped on his or her desk without a solution. Yet presenting a problem in an appropriate way can strengthen your credibility and relationship with your boss. So before going in with a problem, make sure that you have all the facts, have thought through potential options to address the problem, and can provide a recommended solution.

4. Find Ways to Deliver Good News: The goal is to minimize negative experiences and maximize positive experiences with your boss. Try to balance the bad news you have to give with the good news you want to give. Find ways to celebrate little wins. Send emails often of positive experiences and business victories, even if they are small.

5. Maximize “Mind Time:” Don’t believe the “new economy” assertions that face time with your boss doesn’t matter anymore. Time with your boss is still critical to a strong relationship. Yet with all the technological change over the last 20 years, face time should be renamed “mind time.” Communication with your boss can be a combination of email, text message, video conference, or face-to-face interactions. So find the medium your boss prefers and use it to maximize your interaction. Stay on your boss's radar.

6. Never Speak ill of Your Boss to Others: Talking negatively about your boss—or even your job—will eventually come back to bite you. If you tell business associates, suppliers or friends that you can’t stand your boss, you run the risk of your boss finding out. And when your boss finds out, the relationship is jeopardized. So if you have negative feedback for your boss, tell him or her yourself, one-on-one.

All that in 10 years time. Now I'll need another 10 to figure out how to be a good boss myself.


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