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.
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Hopefully, bringing up planned vacation or needed sick days isn’t an issue for you. But occasionally, things come up last-minute that don’t fall in either of those categories. If you’ve worked weekends or nights for a project in a way that’s outside of your normal job description, be sure to request some extra time off in a way that highlights those contributions. If you’re worried about sounding entitled, you can even frame it as a question around company policy, like, “Do we ever offer comp time in exchange for covering events outside of normal work hours?”

If you’re dealing with an emergency, like a flooded apartment or a family matter that doesn’t quite fall under “sick day,” Patrick advises being as candid as possible — without over-sharing — when you approach your boss. While faking food poisoning might be tempting, you never know how a seemingly harmless lie could come back to haunt you.

Either way, when it comes to asking for extra or unexpected time off, you’ll get points for offering to do things like delegating your tasks or picking up slack when you return.
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If you work at a company with fairly obvious career trajectories, this might not be something that keeps you up at night. But if promotions and job titles are more fluid, you could well be losing sleep wondering where you’ll be in a year or two.

Patrick puts it bluntly: The only person who can answer that question is you. Once you’ve looked honestly at your strengths and weaknesses, as well as your career goals, then you can approach your boss with ways to strategize how to there. A good manager will not only be impressed at your initiative; she will also be able to keep you top-of-mind when new opportunities arise that you might not necessarily be aware of.
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If you’ve got a corporate card with clear rules on what you can spend on, lucky you — you can skip this slide. But for many of us, it can feel uncomfortable to raise questions about money, even to a manager.

Ideally, you should ask ahead of time, and with as much detail as possible. “Does this company reimburse gas for work travel?” or, “Is it ever possible to expense cabs from late-night work events?” You don’t want to assume happy hour will get covered as “team building” and then get stuck with the bill for everyone’s pretzels and beer.

However, if unexpected expenses do occur, White suggests framing the ask in a way that makes it clear exactly what about your incurred expense benefits the company. So, for example, say something like “I took out Jessica for coffee and she gave me some great ideas I can use for this project; would it be possible to expense it?”
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I’ve actually had several friends express trepidation and even guilt about taking paid vacation days. But they’re yours — and you’re losing money by not taking them! In general, Patrick advises being in a new job for at least two months before taking time off.

Of course, depending on your role, there might be rules about time off, like not taking off two weeks in a row or during a busy season. You'll want to ask about this well in advance of putting in time-off requests, ideally before you even accept the job. And when you do want to take time off, even if it's guaranteed, you should give your manager as much notice as possible (even if it's months ahead), so it's not a surprise when the actual time-off request comes in.

if its an immovable date, like a reunion or wedding that falls at an inopportune time, double down on offering to help get work done and come up with a thorough coverage plan for while you’re gone — things you should be doing anyway that will really make your boss (and coworkers) appreciate you.
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Imagine psyching yourself up for a raise...only to find out that the budget was decided months ago, and you missed the train. Depending on your company, you may feel in the dark about when, if ever, you'll see a salary boost.

Rather than asking your boss this question outright, however, White suggests doing some research first. Your job offer, Glassdoor, and even your fellow coworkers or HR department can shed some light about when and how raises happen. If it’s on a schedule, then, in all likelihood, those decisions are made months earlier. Instead of asking your boss when they’ll make the decision, you can instead approach her with the request to go over your contributions, so you can make a case for the raise you would like. Patrick recommends keeping a folder with your accomplishments on hand to back you up in these discussions.
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While teachers or salespeople might not be able to make this request, many of us who rely mainly on a computer to get stuff done often long for a day of solitude (or just a day in PJs) working from home. But who gets to work from home in your office — and why — isn’t always abundantly clear. So, when asking, make sure your boss understands why you working from home will benefit the team, not just you. Saying something like, “I know I’ll get this report done faster if I can do it from the quiet of my own home,” gives your boss a chance to get excited at the idea, too, explains White.

Anticipate how you’ll get site-specific work handled (like attending meetings via Skype or having a coworker keep an eye on your desk phone), and you’re even more likely to sell your boss on the idea.
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Patrick emphasizes that this question is possibly the best thing an employee can say to a manager. “Your boss wants to know you’re interested in learning what’s above your job description," she explains.

Definitely let your boss know that you want to be involved as a way to learn more, not just as an excuse to hear yourself talk. Also find ways to contribute, like offering to make the agenda, or taking notes. And prepare to be understanding if your boss says no — the meeting might cover things only upper management is privy to. If that’s the case, you can always follow up with something like, “Please keep me in mind for the next meeting that’s open to junior account managers.”
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You can approach projects or tasks you’re interested in being a part of the same way. Sometimes, it can feel like not getting picked for the recess kickball game if your coworker gets to work on something you’d secretly love to do. But rather than assume it was an intentional decision to not include you, go to your manager with ways you feel like your strengths can serve the project.

If it's too late to be included, then ask about how to contribute to similar projects in the future. As long as you’re prepared to offer examples of what skills you could bring to the table, a good boss loves hearing this question.
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If you’re in an entry-level position, the temptation is there to be available at all times, to everyone. While that drive is admirable, it can also lead to that sinking feeling of realizing you’ve bitten off more than you can chew. Patrick says that this is a situation where an ounce of prevention could save you.

If you don’t already have them, schedule regular check-ins with your manager where you go over workflow and workload, and be honest if someone asks you to take on a task that might be too hard to handle. If you do find yourself with too much to do (and only so many hours in the day), instead of going to your boss frazzled and apologetic, White recommends approaching it as a chance for your boss to communicate what she wants to get first from you.

Try something like, “I’m so thrilled about these projects, but I’d love to get an idea from you about what comes first.” If you know you absolutely can't get something done in time, it’s also better to go to your boss with that as soon as you know, rather than waiting until the day of and praying she doesn’t notice. As long as you aren’t making a habit of it, you and your boss can troubleshoot a solution together.
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There are some bosses out there who don’t like questions, but most will be more than happy to clarify something to prevent a mistake — and maybe more work — down the road. If you have a lot of questions, Patrick suggests being strategic about how you approach your boss with them. Rather than sending several emails or walking over to your boss’ desk repeatedly, try to make sure you have a grasp on all the questions you have and send them all in a single email, or ask your boss if she’d rather meet in person to go over your questions. You’re not expected to know everything, and a good boss is there to help you learn and grow in your role.

Another surefire way to impress your boss? Once she answers your question, make a note of it somewhere and find a way to not have to ask it again.
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There are two reasons you might want to ask if it’s okay to take off: your work is done and you're just wasting time on Faceboook, or you want to sneak out early for a one-time event or appointment. If it’s the latter, ask as far in advance as possible and offer to come in early to make up for it. Your boss might trust you to manage your own time, but it will still look good if you make the offer. Of course, your boss has the right to say no, but as long as you’re not asking to take off at 4 p.m. every other day, she’ll hopefully be accommodating.

If you really are just done with your assignment and twiddling your thumbs, this is another great opportunity to approach your boss with an offer rather than a question. Patrick suggests saying something like, “I’m all done with my assignments for the day, is there anything I can help you with?” Be ready to offer more than once, and if she turns you down, it won’t seem odd if you duck out right at 5 p.m. or maybe even a few minutes early.

Of course, if your boss does give you work, you need to be ready to take it on with a smile. If you have somewhere to be, it might be better to keep busy until around the time other people start leaving rather than trying to leave and instead getting a new task right at the end of the day.
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While discussing promotions and raises within the company can feel awkward, it’s a lot easier than bringing up a future that might not involve the company at all. But asking your boss’ help with moving on might not be as taboo a topic as you imagine. If you’ve established a strong relationship with her, and are at a company with limited growth, it could be a natural discussion to have. That said, it should be something that’s been raised as an option for you before you actually need the reference. Instead, it should start with a candid discussion about how you see an advanced degree fitting into your career trajectory in the near future. Maybe your boss has insight into the degree or schools you're looking into, or could be able to make connections.

Additionally, many companies are willing to rehire employees who left to earn a degree, like an MBA. If you're looking to pursue a degree part-time, it's a great opportunity to sell your boss on how those classes will help not only you but also the company's bottom line. But if the degree means you’ll leave your field or company for good, really evaluate the relationship you have with your manager and whether or not you could harm your prospects at the company should you not get into grad school. If you decide your boss isn't amenable to the idea, seek out a former colleague who has moved on to act as a reference.
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