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5 Questions You Should Ask Your Manager

I once got into a discussion with a friend who was troubled and felt constantly pressured by his manager who he thought was a very difficult boss. He saw him as an obstacle to his work and felt that he was not enjoying his job and was more worried about going to work each day and so on.

But as I continued to ask questions, I was surprised at how little he really knew about his assignments, his manager's expectations, and overall, how to work with his manager effectively. In fact, he tended to make assumptions about what his manager needed or thought, based solely on his observations—without any real facts. No wonder he was struggling!

If you are having similar issues seeing eye to eye with your manager, initiate a one-on-one meeting to ask these five essential questions. You may also feel the need to ask more questions, please do so. With the answers you receive, you will better understand your manager’s point of view, be able to work together more effectively, and, ultimately, create more opportunity for success—for the both of you.

1. “What Can I Do to Make You and Me More Successful This Month?”

This should be a question you ask on a regular basis—because you should always be trying to make your boss as successful as possible.

When you’re able to get a straightforward answer to this, you’ll be able to focus your energy in the right places—because you will know exactly what tasks need to take priority.

(It will also remind your manager that you are truly invested in his or her success.)

2. “What is One Thing I Could Do Differently to Perform Better?”

Having clear expectations is the key to delivering winning performance—and this question is a sneaky way to find out those expectations.

For example, if your manager says he would like you to make more of an effort to actively participate in meetings, you will know that he values a collaborative environment of ideas—rather than coming up with every initiative himself. And knowing that can help you perform exactly to his expectations.

3. “What Should I Know About Your Work and Management Style?”

Does your manager expect you to be available 24/7? Respond to emails on weekends? How does he or she handle stress?

Asking this straightforward question may not get you all the answers (for example, a micromanager may not readily admit to micromanaging). But even if you get just a tiny bit of insight, you will have a better sense of what to expect and how to handle it.

4. “How Would You Like to Receive Feedback From Me?”

No matter what, you my not agree with your manager on everything. But, you do not have to simply remain in frustration.

To prepare yourself for an eventual point of contention, ask how your manager prefers to get feedback—you will get a much better response if you play by his or her rules, whether that means scheduling a one-on-one meeting, rather than catching him or her off guard in a hallway conversation or summarizing your thoughts in an email.

Once you know how to deliver your constructive feedback, you will be much more prepared to ask for what you need: Whether you would like more frequent updates on deadlines, regular one-on-one time, or faster decision-making on projects, it is important to be able to feel comfortable making these requests.

5. “Why Did You Hire Me?”

When you get a new job, you are often so excited that you forget to ask why you were selected over all the other candidates. But this is an important question to ask, because it will help you hone in on exactly how your boss believed you would make the team better.

Perhaps your boss will say that you demonstrated your ability to present complex data in a simple way better than any other candidate. And so, now you know that’s a major part of what your boss expects you to deliver. By spending some time in your manager’s shoes and asking these questions, you’ll be able to smooth out any rough edges of your professional relationship.

OK—it might be a little intimidating at first, but give it a try. As you build that rapport, you will stop seeing your manager as an obstacle and start seeing him or her as an essential part of your mutual success.


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