8 Get-Ahead Questions to Ask Your Boss

8 Get-Ahead Questions to Ask Your Boss

You'll likely have several bosses in your lifetime. Some will be chummy and others you'll only hear from at performance review time.

When it comes to your career, flying under the radar isn't a great strategy. Getting honest input from your supervisor is crucial to your relationship with your boss — and that relationship can have a big impact on your career.

Plus, it 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.

Read on for questions from an expert that will help you and your supervisor get on (or stay on) the right track.

1. How was your weekend?

When to ask: “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: By understanding how she spends her time when she’s not at the office, you’ll learn what’s important to her.

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

When to ask: This is a great query if you’re new to a job or team, because it will give you insight into the demands of the job. Or, ask when a new supervisor joins your department; it will help you discover his priorities. But you can also use this question anytime, say when your boss has a lot on her plate and you want her to 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 your best employees, what makes them stand out?

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 performance review, or at a time when your boss has just given you a bit of tough feedback.

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.

4. I’m really excited about working on ________ together. Can I 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 get feedback once you’re underway.

Why it’s important to ask: “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. "By asking for guidance upfront, you’re saving yourself — and your boss — from disappointment and wasted time,” advises Glickman.

6. I’d love to oversee _________. 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.

Why it’s important to ask: “Managers love employees who are excited to learn, grow and take on new responsibilities,” Glickman says.

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 answer during your performance review, but, if not, you should ask. If you just had a review, and you don't feel that this information was offered, request some one-on-one time.

Why it’s important to ask: “There are probably 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.”

If your boss says that you’re doing a great job and you don’t need to change a thing, 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 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 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 taking a few days to collect your thoughts, you’ll have time to reflect 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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