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8 Questions You Should Ask Your Boss To Get Ahead
If you think about it, you, probably, only hear from your boss when 1) you totally mess up, 2) you do something majorly commendable, or 3) it is performance appraisal time.
Getting honest feedback from your supervisor is crucial for your relationship with him or her unless you are happy flying under the radar, which certainly won’t help you advance. Like it or not, your bond with the dominant patron can either make or break your career.
A strong rapport makes deadlines easy and the workday go by in a flash. A shaky one, however, can make even a short walk incessant and mundane.
Communicating with your boss, at a comfortable level, might be easier said than done, but this should not discourage you from getting the most out of him or her. Successful people only get what they want when they chase it. More importantly, bosses are not just there to tell you what to do. They have the ultimate responsibility of grooming and developing the people who will, one day, take their place. And that is you!
Having a healthy relationship with your boss might also reduce the workplace stress. In a study conducted by the American Psychological Association, 75% of participants claimed their immediate boss to be the most stressful aspect of their job.
Here, we have shared a few key questions that you can and should ask your boss to help you and him/her get on or stay on the right track.

8 Questions You Should Ask Your Boss To Get Ahead

1. What Is The Most Important Milestone You Hope To Achieve In Your Life?

This question will give you a quick insight into your manager’s short-term plan, providing you with a better idea of what your goals and objectives should be. Unfortunately, bosses are not always clear with employees on their motivations. If you are able to understand a bit more about what your supervisor is focused on, you can prioritize your own responsibilities and position yourself for success in your boss’ eyes.
For instance, the manager’s goal, during your organization’s acquisition, is to create a smooth transition for the newly merged department. Now, whether that means spending a few weeks beefing up company’s documentation or simply training the volunteers, you should be aiming to help him/her succeed in that.

2. What Keeps You Awake At Night?

According to Andrea Ballard, owner of Expecting Change, this question can provide a perspective for both you and your boss. The answers will vary widely, depending on the manager. After attending a presentation titled  “The 5 Things That Keeps Your CEO Up At Night”, Ballard got back to her office to share the question with her boss, to which the CEO answered, ‘’Wow, I could sure add a few”. And he eventually opened up and shared prospects that were completely new to her. She offered to be a mock audience for him and viewed his presentation wholly to provide feedback and develop an altered frame of reference for herself.

3. How Did You Get To Where You Are Today?

Asking this question shows that you’re focused on developing your skills to achieve the same progressive standing as your boss – if not further. It is also a great way to get some expert advice on what to do and what not to do in your career.
[RELATED: Interview Questions to Ask During YOUR Interview]

4. What Should I Know About Your Work Style Management?

Does your manager expect you to be available 24/7? Send in and respond to emails on weekends?
Just as a micromanager will not easily admit to micromanaging, asking these questions, straightforwardly, might not get you all the answers. However, even if you can get a tiny bit of insight, you will have a better sense of work expectations and how to handle them.

5. What Do You Think of The Employees Who Have Previously Worked For You?

Reserve this question for a time when you’re in a serious ‘getting feedback’ mode, like during a performance evaluation or at a time when your boss has just given you a bit of a rough appraisal. As a task in any employee’s job description, this question can be a good signal to show that you want to improve in your skills, to make his or her job easier.

6. What’s One Thing I Can Do Differently?

This question is a sneaky way of finding out the expectations necessary for a winning performance. For example, if your boss asks you to participate in meetings more, you will know that rather than coming with every initiative on their own, s/he supports a collaborative environment of ideas. Being aware of that can help you cater exactly to his or her business notions.

7. Why Did You Hire Me?

When you are newly hired at a company, you often forget to ask why you were selected over all the other candidates. This is an important question to ask because it lets you zero in on exactly what your boss believed you would do to make the team better.
Your boss can, perhaps, say that unlike any other candidate, you have the ability to present complex data in a relatively simple way. So, now you know what exactly your boss expects you to deliver and, hence, you can work on getting better in that particular area, in future.

8. Want To Grab Lunch?

This question is recommended for team-building and connections, even though very few employees think of asking their bosses. Ballard says that going for lunch or drinks after work with the boss once in a while is reasonable.
Try and ask a few times to see how they receive it. Some managers might not want to socialize outside work for the fear of looking like they are playing favorites. But in case your boss is up for it, just stick to neutral, non-work topics for striking up a conversation.
At the end of the day, believe that your boss is the ally to your success. The desire to bring out best in people is something that s/he has definitely thought about. But you need to help and guide them as well. Sometimes s/he is just busy as you, focusing on the tasks assigned to them by their supervisors. So be fair and don’t expect them to second-guess every initiative you take at work. The definition of success might just be one spoken word away.

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