How to phrase 8 awkward questions you may want to ask your boss

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Think about the best way to ask these questions.
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Open and honest communication is a hallmark of a positive workplace culture.

“In fact, several studies suggest that one of the most important indicators of future financial success in a business is the ability for employees to be able to speak candidly without fear of retribution,”says Michael Kerr, an international business speaker and author of “The Humor Advantage.” “Part of being able to speak openly is feeling comfortable asking your boss anything – including some potentially uncomfortable questions.”

Asking difficult questions at work can be challenging at the best of times – and it’s only natural, given the power dynamics, that asking your boss something awkward is that much more difficult. “But suppressing questions can lead to low morale, more stress, and, by ignoring the proverbial elephant in the room, can create even larger conflicts down the road,”Kerr explains.

Here are a few ways to rephrase some potentially challenging workplace questions we’ve all wanted to ask at some point:


‘Can we wrap up this meeting?’

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If you have a call to get to or a deadline to make, and you’re in a meeting that seems to be going on forever, you may want to ask your boss to wrap it up.

“But asking your boss to keep it on track, keep it focused, or to end it on time can be awkward because you run the risk of coming across as criticizing their ability to run meetings effectively,” says Kerr. “You’re also in danger of looking like you’re just not interested in the topic at hand or not being a ‘team player’ if it’s a team meeting.”

Kerr’s advice is to “focus on the positive benefits of ending the meeting on time, be proactive, and request it in such a way that you’re involving your boss in the solution.” He suggests something like: “As I’m sure with everyone, I’ve got a lot on my plate this afternoon. What do you think we might be able to do to help everyone stay on track by finishing the meeting on time?”

“This is far more positive and it opens up the conversation to explore potential solutions that include your boss.”


‘Why are you ALWAYS so negative?’

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Dealing with a negative boss is never easy, but phrasing a question this way will only get their hackles up because it will come across as a character assassination, and even make it sound like you’re the negative person who’s not open to hearing tough criticism, Kerr explains.

“Instead, try using ‘coaching language’ that focuses on behaviors, which are objectively observed, rather than subjective opinions about character or attitude,” he says. “Try to preface the question with a statement that lets your boss know how their attitude makes you feel and what the negative consequences are of that behavior. Then use the question to ask for input on your own behavior, which will help show that you are open to changing your behavior as well.”

For example: “Whenever you roll your eyes and focus on only the downside of my suggestions, it makes me feel like my contributions aren’t valued and like we can’t have a frank debate and discussion to see if there’s something that’s worth exploring. Is there something I should be doing to make sure my ideas get a fair hearing and that would help us both focus on the potential positives?”


‘Why haven’t I received a raise yet, even though you promised me one?’

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Bringing up money, promotions, or raises are some of the most difficult conversations to have with any boss for a number of reasons, one being that it opens up the possibility to hear some uncomfortable truths about your work performance, says Kerr.

Asking the question in a manner like this will make you sound accusatory, so rather than assuming wrongdoing on your boss’s part, stay neutral and focus on yourself: “When I moved over to this department last fall we had discussed a raise, so I’m just wondering: Is there something I need to be doing differently to help make that happen?”


‘I drank a bottle of wine on that last sales trip meeting — I can expense that, right?’

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Getty Images/Justin Sullivan

“Asking an expense question in this manner might make you sound cavalier in your attitude, or may come across as sarcastic,” Kerr explains. “Always be professional, and focus on wanting to do the right thing for the company.”

Try something like: “I want to make sure I am completely above board and following protocol – do you know if it’s okay to expense alcohol, and who I should talk with to make sure I’m consistently doing the right thing with my expense reports?”


‘Why did Jane get the corner office and not me?’

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Expressing disappointment is always uncomfortable because it can make you feel as though you are whining and you have a sense of entitlement. “And posing a difficult question in this manner will make you sound confrontational or petty, and will only serve to put your boss into a defensive stance,” Kerr says.

“It may also make it seem like you are taking a pot shot at a colleague,” he adds. Instead, express your disappointment and focus on your own behavior.

He suggests you say something along the lines of: “I’m really disappointed I didn’t get the corner office as I really do feel as though I’ve earned it, and as you know I can sure use the extra space. Is there something we could explore together as an alternative solution or is there something different I should be doing different that would help me gain more recognition?”


‘Since you let everyone else do it, could I work from home more frequently?’

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Samantha Bennett/Flickr

“Again, this can come across as confrontational and negative,” Kerr says. “And using a phrase such as ‘everyone else’ or ‘everyone except me’ definitely makes it sound like you are playing the ‘poor little old me’ card.”

Whenever possible, avoid talking about other people, and instead focus on yourself, what you can control, and what’s best for the company.

Try: “I can see a lot of benefits to telecommuting for the company, for example, better productivity and much happier employees – so I’m wondering: Could we explore some options to see if it might be doable in my own position?”


‘How do I get the same treatment as John?’

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“Ouch,” says Kerr. Accusing your boss of anything – especially something like favoritism – isn’t a great idea.

“Keep your emotions in check and focus on yourself,” Kerr advises. Say: “I feel as though sometimes I’m overlooked for certain projects. Is there something I need to be communicating better or doing differently to get noticed with my performance?”


‘I really can’t tell — are you joking or being serious?’

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If you don’t know a person well, you may have trouble reading their sense of humor.

For instance, if you’re a new employee or have a new boss, it may take some time to figure out if or when they’re joking around, or being completely serious – and you wouldn’t want to mistake one for the other!

“No one likes to be told they don’t have a sense of humor or that their attempt at humor missed the mark,” Kerr explains.

So the next time the boss says something like, “Oh, sure, take as long as you’d like to finish the project!” instead of asking them so bluntly whether they’re serious or not, try this: “As we’re getting to know each other better, I just want to make sure we’re very clear in our communication. When would really like me to finish the project?”