How to Manage Your Boss

By Jean Kelley

No matter where you work, you report to someone - maybe even to two or three bosses. And whether you think your boss is brilliant or a bore, the fact is that you have to manage the relationship with your boss if you want to advance your career.

Realize that you are more dependent on your boss than your boss is on you, because your boss holds the key to your short-term future. Not only can your boss release you at any time, especially in today’s economy, but your boss can also unconsciously ostracize you by not keeping you in the communication loop and by giving all the desirable projects to others. When your boss senses that communication between the two of you is not going well and situations have not been resolved, he or she will simply go work with your co-workers rather than you.

Therefore, if you don’t manage the relationship with your boss, you won’t last long in your particular position - either you’ll get fired or you’ll quit. Granted, if you work for a large company, you might be able to transfer to a different boss. But even then if you don’t know how to manage your boss you could end up repeating the same scenario as you did with your former boss.

So before you let a little mismanagement on your part disrupt your career, take some time to learn the keys of “boss management.” The following suggestions will get you started on the right path and contribute to a more harmonious work day.

Find out from your boss what “good” looks like and all who are involved in measuring “good.”  Whether you report to one person or four different bosses, you need to make sure you’re meeting everyone’s expectations. After all, what seems good to you may only be mediocre to your boss. Therefore, find out what “good” looks like to each boss you report to. You could simply ask, “What does ‘good’ look like on this project?” Or, “If this went exactly like you wanted it to go and it turned out perfect, what would have to happen between now and that time?” As an added benefit, you might even get an idea of the scope of how big that project really is. Sometimes bosses don’t tell you much and you have to pull it out of them. If you do this simple step upfront and find out what the expectations are on the project and the timelines, you save a lot of time in the end.

Ask your boss what kind of follow up he/she wants and what your boss has to have for his/her comfort level: Many times bosses expect people to be mind readers, simply because they’re busy and can’t always go over all the details of a project. As such, your boss might forget to tell you such things as a firm deadline or a required step. And since everyone operates from their own set of realities, the possibility of miscommunication is high. That’s why you need to take the initiative to set expectations for every project your boss assigns you. You need to find out: “What is the deadline? What are my resources? What checkpoints or milestones do we want to establish, if any? What step or contact person is absolutely critical to this project?” Just as you set expectations when dealing with clients and co-workers, you need to manage the relationship and set expectations with your boss every time.

Examine your boss’s style and adjust to that style: Peter Drucker says there are two key leadership styles: readers and listeners. Which is your boss? The readers want data before you talk with them. The listeners want to talk before they read. For example, a CEO has a controller who is good with the numbers. He gives his boss elaborate and spectacular reports…but that’s not what she wants. Every time he gives her a report, she pushes the report aside and starts talking with him. She’s not a reader; she’s a listener. All she wants to know is the bottom line - “Are we in trouble or not?” So this controller is spending precious time producing materials his boss doesn’t want. Conversely, if your boss is a reader, you’re not going to get a good decision from that person in a quick hallway conversation. Readers can’t make fast decisions on complex issues without data. So unless it’s an easy question, they need to think things over and analyze them. And while there are many personality types in the workplace, if you can make this one distinction between the readers and the listeners, you’ll go far with managing your boss.

Muster up the courage to tell your boss when you feel you haven’t been fully heard: Communication has to go both ways for success. If your boss upsets you or misunderstands you, you have to speak up - not from the head, but from the heart. One way to do that is with an “I” message. For example, “I was really upset and hurt by what you said. I interpreted it as __________. Did you mean it that way?” Most people want to be heard, yet most don’t get heard by their boss. Therefore, it’s your responsibility to say when you’re not feeling heard. If you’re leery of speaking up to your boss, first try this approach on your family members. Practice it in a safe environment before trying it on your boss.

Become aware of other managers’ styles, especially when they have a stake in the outcome of your project: Keeping up with the expectations and styles of multiple bosses can be a fine balancing act. The only way to wade through it all is if you can keep in mind the one thing that matters most to each of the stakeholders you have to please. It’s too overwhelming to have five stakeholders and think through five requirements for each. So either ask each person what is most important to him/her, or figure out what you have observed in each person’s behavior that you can attend to.

Manage Up: The good news is that no matter how well or poorly you have managed your boss’s relationship in the past, you can re-craft your relationship on every new project. Ideally, you want to create a relationship where talking from the heart is the norm, as then confrontation on serious issues won’t be difficult. In the end, it’s really about understanding your boss. When you teach your boss how to work with you and hone great communication skills with him or her, your work life will be happier and much more productive.

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