8 Get-Ahead Questions to Ask Your Boss


ask bossThink 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.”

RELATED: Quiz: Would You Make a Better Boss Than Your Boss?

  • jimmy

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