How to ask your boss these 8 awkward 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: 

'Why are you ALWAYS so negative?'

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?"

'Can we wrap up this meeting?'

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 haven't I received a raise yet, even though you promised me one?'

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?"