8 Questions to Ask Your Boss to Get Ahead

Think about it: You probably only hear from your boss when a) you royally screwed up, b) you majorly kicked ass or … c) it’s performance review time.

Feedback from your supervisor is what you crave, unless you’re happy flying under the radar, which certainly won’t help you advance. Getting honest input from your supervisor is crucial to your relationship with your boss—and, like it or not, your relationship with your boss can make or break your career. A solid rapport makes deadlines a breeze and the workday go by in a flash; but a shaky one can render even a short elevator ride interminable.

Plus, having a good relationship with your boss may even reduce stress at work. In a workplace study by the American Psychological Association, up to 75% of respondents said the most stressful aspect of their job is their immediate boss.

Here, we asked an expert to share a few key questions you can ask that will help you and your supervisor get on (or stay on) the right track.

1. How was 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.” Try to ask something specific, like if her daughter won her softball game or how the client dinner went—it’ll show you’ve been paying attention.

Why it’s important to ask: The more you know about your boss, the better. By understanding how she spends her time when she’s not at the office, you’ll learn what’s important to her. “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.”

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

When to ask: This is a great query to bring up if you’re new to a job or team, because it will give you insight into the demands of the job. Another good time to ask this question is when a new supervisor joins your department; it will help you discover what his priorities are during the transition. But you can also use this question anytime, say when you notice that your boss has a lot on her plate and you want to let her know you’re available to pitch in, which can boost your “invaluable employee” quotient.

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.

3. 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 the type of question to pop as you head out to pick up a sandwich together. Reserve it for a time when you’re in serious “getting feedback” mode, like during a performance review, or at a time when your boss has just given you a bit of tough feedback. This question can be a good way to signal that you want to improve and learn skills that will make her job easier—a task in any employee’s job description.

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.”

4. 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: Anytime you start a new project, work with a new team, or work on a long-term assignment, let your manager  know upfront that you’d like to sit down with him and get feedback from him once you’re underway.

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.

5. 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: At the onset of a project that’s unlike anything you’ve ever tackled.

Why it’s important to ask: Most likely your boss has a vision of how she’d like a project completed, and if you don’t have a clear sense of her expectations, she’s bound to be disappointed. “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.”

6: 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 excelling in your current role and ready for a new challenge—and you know your workload won’t suffer for it.

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.”

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

When to ask: Ideally, these are questions that your boss will naturally answer during your performance review, but, if not, you should feel free to ask. If you just had a review, and you don’t feel that this information was offered, send your boss an email to request some one-on-one time and tell him that you’re hoping to answer these specific questions.

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.”

If your boss evades these questions—and says that you’re doing a great job and you don’t need to change a thing, but you know there’s room for improvement—you can gently press the issue. Try a follow-up question 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?”

8: 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: At the end of a not-so-great performance review or any conversation wherein your boss gives you valuable, if not altogether positive, feedback.

Why it’s important to ask: It’s hard to think on your feet and ask constructive questions when you’re feeling beat up. By asking for a few days to collect your thoughts, you’ll have time to reflect on your boss’ words and brainstorm ways to move ahead. “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.”

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