Just consider: You probably only receive communication from your supervisor when

  1. You made a terrible mistake.
  2. You were absolutely amazing!
  3. It’s time to evaluate and assess our performance.

Feedback from your supervisor is essential to help you further yourself in the organization and reach success unless, of course, you enjoy staying under the radar. It’s vital that this feedback be honest as it will form a strong bond between you and your boss- one that can either propel or hinder your career. So don’t forget to seek out these important insights! When there is a strong relationship between coworkers, deadlines become easy to meet and the workday passes by quickly. However, when communication isn’t consistent or reliable even an elevator ride can seem like an eternity.

Having a positive relationship with your boss can potentially drive down stress levels in the workplace. A recent survey from the American Psychological Association revealed that as many as three-quarters of respondents reported their direct supervisor to be one of the most stressful facets of their job.

To ensure that you and your supervisor remain on the path to success, we’ve consulted an expert who has provided a few key questions to ask.

How did you spend your weekend?

When to ask: “Monday mornings are hectic and everyone’s got a million things on their to-do list—but don’t overlook the opportunity to ask about your boss’ weekend,” suggests Jodi Glickman, author of “Great on the Job: What to Say, How to Say It: The Secrets of Getting Ahead.“ It gives you an opportunity to start building a personal relationship and connect on a non-work level.” Show that you are invested in her life by asking personally tailored questions, like did her daughter win the softball match or how was dinner with the client? Doing so will show that your feelings for her go beyond just small talk. This simple interaction will be sure to make a positive impression!

Why it’s important to ask: Knowing your boss personally will bestow you with an edge. By learning how they invest their time outside of work, you can gain insight into the things which matter most to them. “It allows you two to build a real relationship that extends beyond spreadsheets and timelines,” Glickman explains. “It gives you another dimension to connect on so she also sees you as not just a subordinate but someone with a personal life and outside interests, too. Furthermore, by sharing personal details about your life, you will appear more mature and invested in the relationship. That scores big points with management.”

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What’s your biggest problem—and how can I help you solve it?

When to ask: If you are fresh to a position or team, inquiring about the job requirements is an excellent way of gaining insight. In addition, if your division has just recently appointed a new supervisor, it would be wise to ask this question in order to understand their primary focus during the transition. Moreover, this inquiry can be asked whenever you notice that your boss is overloaded with tasks; in doing so, it will show her how “invaluable of an employee” you are and offer to help out wherever possible.

Why it’s important to ask: “It shows that you’re someone who is strategic and thoughtful and who takes initiative—you’re not just waiting around to be told what to do,” says Glickman.

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When you think of the best employees who have worked for you, what makes them stand out in your mind?

When to ask: This isn’t something to ask your boss while you’re grabbing a sandwich together. Save it for more appropriate occasions when you are actively seeking feedback, such as during a performance review or after receiving constructive criticism from them. Asking this question is an effective way of demonstrating that you want to grow and learn skills that will make your job easier – something all employees should strive to do!

Why it’s important to ask: “If you’ve got a good relationship with your boss, but you’re looking to take your game to the next level or score a promotion or a raise, this is a great way to discover what she values most,” says Glickman. “Once you find out, you can try to model some of those behaviors.”

I’m really excited about working on ________ together. Would it be possible to get some feedback from you over the course of the project?

When to ask: When embarking on a newly-initiated project, working with an unfamiliar team, or taking on a lengthy assignment – always make sure to inform your manager that you would appreciate their feedback and guidance as the task progresses.

Why it’s important to ask: Every time you ask your boss after an important meeting, “How’d that go?,” invariably he’ll tell you did a great job. “The best way to get real and meaningful input is to plant the seed in advance and ask your boss for feedback before you need it,” says Glickman.

I really want to nail the ________ assignment. Do you have any templates I could reference, or is there anyone on the team I should speak to who’s done a good job on one recently?

When to ask: When beginning a new project that is completely foreign to you.

Why it’s important to ask: It’s essential to have an understanding of your employer’s expectations if you intend to satisfy them and meet the project objectives. Otherwise, they are sure to be dissatisfied with the outcome. “You don’t need to reinvent the wheel when you get a new assignment,” advises Glickman. “Be resourceful and ask to see examples of a job well done. By asking for guidance upfront, you’re saving yourself—and your boss—from disappointment and lots of wasted time.”

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I’d love to oversee _________ in the next six months. Could we keep that in mind as projects are being assigned?

When to ask: When you’re already succeeding in your current role and are prepared to take on a new challenge, but don’t want the extra stress of more work; it’s time for a change.

Why it’s important to ask: “Managers love employees who are excited to learn, grow and take on new responsibilities,” Glickman says. “When it comes time for promotion, you will fare well as someone who not only does a good job, but is always eager to develop new skills and add the most value to your organization.”

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What should I start doing? What should I stop doing? What should I continue doing that I do well?

When to ask: It would be perfect if your boss addressed these questions during your performance review, but don’t hesitate to inquire if he didn’t. If you just had a review and were not provided with this data, send an email asking for individual time with him or her and let them know that the purpose is to answer these particular queries.

Why it’s important to ask: “There are probably a lot of things you do well that your boss loves and probably others that he wishes you’d stop doing, but he never really had the heart or stomach to tell you,” Glickman says. “This line of questioning makes it easy for him to finally tell you that the 10 hours of cold-calling you’re doing every week isn’t leading to results, and you’d be better off building out the focus group strategy instead.”

Even if your boss insists you don’t need to change a thing and that you’re doing great, chances are there is still room for improvement. Don’t be scared to push the issue further and ask more questions until you reach an agreeable resolution. Try to send a follow-up message like, “I really appreciate hearing everything is going well, but I’d really like to move up a level and challenge myself. What else should I be doing to make sure I get promoted next year?”

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I’m sure that I’ll have some additional thoughts and questions as I digest all this information. Could we schedule a follow-up conversation in a few days?

When to ask: After a less-than-satisfactory performance review or any conversation wherein your manager provides you with helpful, albeit not entirely positive, feedback – it’s time to move forward.

Why it’s important to ask: It can be difficult to think of pertinent and productive questions when you are feeling discouraged. If you take a couple of days to reflect on your supervisor’s words, it will give you the time needed to come up with strategies for making progress. “The last thing you want to do is lose your cool,” says Glickman. “Remember, the goal of feedback is not to make you feel good. It’s to make you better at your job.”

What additional questions should you ask your boss? We’d love to hear what you come up with in the comments below!

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