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7 Questions to Ask Your Boss on a Regular Basis

The squeaky wheel gets the grease in this situation.

As an employee, receiving feedback and input is important– "no news is good news” doesn’t always apply. Often, "no news" might mean that a manager is too busy, and as such, has difficulty finding the time to provide feedback. Or,  your boss might prefer to "let things slide" vs. confront a tough situation the way a manager should. At the same time, it is part of your boss's job to be present for you to ask questions and learn from them. Also, many managers get so caught up in their day to day activities that it can be a nice reward to know that their employees genuinely care about what's going on with them and the work group.

With that said, communication is a two-way street. If you have questions, then ask. Or, if you don't have questions, then consider taking this article to heart and begin asking some. Doing so might present you with a perspective you hadn't considered, provide valuable career guidance, and will show your manager that you're interested and care. Below are some questions that can be valuable to ask your boss on a (fairly) regular basis.   

1. How am I doing?  

You might not always like the answer to this question, but it's an important one to ask your boss. If you get a simple answer like "You're doing fine," or "All's good," then you might follow-up with another question that asks if he or she has any suggestions for improvement.

2. What type of training would you recommend for me to advance in my career?

This is a good question to ask on a quarterly basis, especially if you keep getting the same answer with the "How am I doing?" question. With each quarter and the passing of time, your manager might think of some new career developmental opportunities to help you advance and learn. This is also a great question to ask if you receive negative feedback or during a performance appraisal.

3. How would you have approached this project or situation?

This could be a pre-emptive question, as well as a question for after the fact. It's also a question to ask even if you received positive feedback on a project or task, as you might learn a new and improved way of doing or approaching a task that you hadn't considered.

4. How are you doing at this moment?

When you ask this question, do so with the intention that you care about your boss's answer. Though he or she might be too busy to give you a lengthy answer at the time, your genuine nature won't go unnoticed.  

The answer to this question also gives you some insight as to why your manager might be acting a certain way in the days and weeks to come (if they seem to be sending out negative vibes, for example, it could be because they're having a tough week or are missing deadlines). At the same time, don't anticipate that your boss will provide too much personal detail, as doing so is considered unprofessional in some workplace cultures, but if you're intuitive, you'll be able to read between the lines based on the tone, body language, and words you experience from him or her.

5. What's your preference when it comes to communication?

It's good to ask this question when you first start working for someone, as well as at the beginning of any new project or issue. The purpose of this question is twofold—to find out the communication medium preferred, as well as the frequency of communication desired. Do they prefer email, phone or in-person communication, for example (i.e. the medium)? And do they prefer to be updated about projects or work-related issues as they're happening, once they're completed or resolved, or do they prefer weekly updates (i.e. the frequency)? Is there an expectation that you return emails on weeknights and weekends, as well?

Effective and clear communication with your boss is very important for the relationship to be successful, and if you try to meet your boss on his or her terms on this one, you'll be ahead of your peers.

6. What path did you take to get to where you are today?

I love asking this question during interviews, as interviewers typically love to share; and it shows you're interested in learning from what they have to say about career development. If you don't ask this question during the interview, or you have a new manager or boss at work, then be sure to ask this question to learn and show interest in your current job position.

7. What types of networking events and professional organizations do you find the most beneficial?

Networking will help you advance in your career, and it can help you find another job, position or promotion in the future. Whether your boss has a lot or a little more experience than you, getting his or her input on this question and what's worked well for him or her is valuable information to tuck away in your arsenal of career management resources.

If you have any qualms about asking your boss questions or feel intimidated or a bother, then take a step back and make an effort to understand your manager's perspective and know that many managers want to be there to support you, but have a challenging time finding the time to do so. Once you begin asking them these types of questions, it will help you foster a productive relationship with him or her, which will make it easier for you to approach him or her for feedback and information on a regular basis.

As an employee, it's not only your right to ask questions, but it can also show initiative on your part while providing you with valuable information to grow and evolve in your career. Who knows–you might even decide to expand your list of questions to your co-workers and other supervisors, as well!

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