How well do you know your boss? I don’t just mean her preference for double shot lattes or that she likes to squeeze in a midday gym class on Wednesdays. In order to be successful at work, it’s worth getting a little curious about your boss’s background, her values and her day-to-day management style. While some of this information can easily be gleaned from LinkedIn, having a casual conversation with your boss is another great way to gain valuable insight into her professional goals. The more you know about her values, management style, background and interests, the greater the likelihood that you’ll find success at work.

These are six good questions to ask your boss:

#1: What are you being measured on and how can I help you achieve these goals? Understanding your manager’s objectives (e.g., doubling year-on-year sales) is your key to success. By understanding how your job performance impacts hers, you can better position yourself to support her success – and yours.

#2: How often do you want status reports/project updates? Working for a micro manager and then suddenly getting assigned to a supervisor with a hands-off style requires a huge shift in your approach to daily tasks. Know your manager’s preference for daily or weekly status updates so you can better anticipate her needs and strike the right communications balance.

#3: How important is face time? This can be a difficult question to bring up, but it’s an important one to ask. If face time is extremely important to your boss, then it’s critical to ensure that your in-office schedules overlap. On the other hand, if your boss values autonomy or expediency over face time, you’ll have more leeway to request telecommuting or flexible hours.

#4: What did your boss do before her current job? We often think of our bosses “all knowing”, but we’ve all had supervisors who were new to the industry or lacked a robust understanding of how to handle all the responsibilities on their plate. Understanding what your boss did in his previous job will enable you to better help your boss shine if he’s weak in one area, and you’ll look good in the process, too.

#5: How did your boss get his current job? Was your boss promoted because someone was fired and he stepped into the breach? Did he get the job by default because he was next in line, or did your company proactively recruit her for the position? This will help you understand how your boss fits within the larger corporate structure while also providing insight into what other people think about your boss.

#6: What does your boss want to do next? Understanding your boss’s career goals will help you proactively position yourself as a valuable ally – rather than inadvertently becoming an obstacle to your boss’s next big thing.

Taking the time to ask your boss or manager questions will not only help you better understand your boss, but also give you a leg up when it comes to succeeding at work.

How well do you know your boss and his or her professional goals? What questions have you asked to help strengthen your relationship and improve performance? I welcome your feedback on the most important questions to ask your manager in the comments below.


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