All The Questions You’re Afraid To Ask Your Boss — & How To Ask Them

Asking your boss a question can be intimidating. Whether you're worried you're overstepping or that you might simply look dumb, it can be tempting to keep your mouth shut and just wing it. I've commiserated with friends as well as coworkers about being hesitant to ask for everything from time off to help prioritizing work. To figure out the best way to ask the questions — and how get the answers I want — I talked to two women at different stages of their careers.

Kate White, former editor-in-chief at Cosmopolitan and author of I Shouldn't Be Telling You This, has managed plenty of up-and-coming writers and editors over the years and emphasizes that whatever you ask, the question should be framed in a way that helps your boss, not just you. You working from home sounds a whole lot better if you frame it as a chance for you to really tackle a big project in solitude, for example.

Arielle Patrick may not have White's years of experience, but at 27, she's already a manager at a global PR firm and has been compared to Scandal's Olivia Pope. With recent experience as both a manger and an entry-level employee, Patrick emphasizes how important it is to ask questions in exactly the way White outlines above. "Part of punching above your weight is working on your confidence level — and being a team player." Getting up the courage to advocate for yourself productively is also a way to help bridge the much-discussed confidence gap that plagues women in the workplace.

So if you have a question you've been sitting on for a long time, read on. If you ask it the right way, you might not only get what you want; you may also impress your boss.