5 Tips for Discussing Important Issues with Your Boss

5 Tips for Discussing Important Issues with Your Boss, workplace conflict resolution

Summer is time for sun, beach days, and taking the occasional day off of work. Asking for time off can be so uncomfortable, even if you’re allowed a certain amount of vacation days per year. One of the main pros of working remotely is avoiding this situation, or more easily just doing your work in advance. Still, it is important to communicate with your boss and your co-workers to know exactly what needs to be done before you leave. Like I said, though, this is challenging. We don’t want to disappoint anyone, and yet we need to make certain decisions to benefit not just our careers, but also our social, personal, and home lives. Failing to have important discussions at work can bring down each of those critical areas of life.

Vacation time isn’t the only reason you’ll have to bring something to your boss’ attention. What if you have a major issue with a co-worker? Think you should be considered for a promotion? What if you want to interview somewhere else for a new position? Perhaps you made a huge mistake on the company’s behalf, and you now must explain this to your department head. Making these types of conversations fun might be a stretch, but keeping them pleasant, professional, and to-the-point is certainly not. Let us help! Here are a few ways to make these conversations easy as can be.

The Prep Work

Think Ahead: Keep Communication Flowing

Try to begin on the right foot with your boss. Even if he or she is not the nicest, it will make it less stressful to approach them later on if you are in regular contact. You won’t have to worry about suspicion or skepticism on your boss’ part, and you won’t have to work yourself up to visit their office (that’s the worst part, isn’t it?). Keep them updated on your projects throughout your time there, and ask if there are projects with which you can assist. Or, just stop by to say hello and check in. However you choose to approach this method, it is a useful way to make life easier for your future, stressed-out self.


Do Not Be Aggressive


Going in with attitude will almost certainly make your situation worse. Even if the forthcoming discussion is not going to be about something nice and pretty, you can still maintain professionalism by keeping your cool. Calmly explain your situation without blowing up. If your boss starts to get a little wild, uphold your composure. Yelling or making accusations will only anger your boss even more, and you may end up in a more unfortunate situation than the one with which you began.

The Discussion

Describe the Problem…And the Solution

Harvard Business Review (HBR) suggests going right in with the problem itself, describing in detail the issue at hand, and how it specifically impacts “your work and the company’s goals.” Don’t be afraid to give specific numbers or details about the problem, so as long as it’s relevant to the reason you bring it up in the first place.

The next step, according to HBR, is discussing the ways you have already tried to solve the problem, and “what you’ve learned from those attempts.” This will make it clearer to your boss that you have a) put effort into solving this issue, b) aren’t just screwing around and wasting time sitting at your desk, and c) know how to do your job. Present your manager with all possible solutions, and propose your best bet (and by “best bet,” I mean “most logical solution with the most probabilistic outcome).”

Perhaps yours will be the winning one, or your boss might suggest something entirely different. Regardless, you are demonstrating those three points I mentioned, and thus proving that you are a conscientious employee that is not a money-suck for the company. Believe me; that’s always the bottom line.


Take Responsibility




No matter the problem, the solution, or the cause, if the problem pertains to you, accept the consequences. Own up to the outcome and take whatever comes your way as a result. You might believe that the first line of attack will be you getting fired; that’s why these conversations can be so nerve-wracking. Believe it or not, the company may lose money by firing you, so they’ll try not to fire good employees. Even good employees make mistakes. By showing that you are a good employee that has made a mistake, odds are, you won’t get fired. This isn’t to say that this doesn’t happen, but you shouldn’t try to side-step these conversations to avoid an outcome that may not be realistic.

And remember: discussions like vacation days and personal issues should not be discussions that lead to dramatic outcomes. If your employer threatens to fire or penalize you for days to which you are entitled (assuming you’ve taken all responsibility and done your work otherwise), this may be a problem for human resources.


These two points go hand-in-hand. It will only look bad for you to say that it was a co-worker’s fault, or that it was not your own fault. That won’t do anyone any good at all. It won’t make anyone else look bad; it will only make you look careless and spineless. As an adult, it is important to maintain your dignity, but also to maintain an office reputation as an honest, hard worker.

I encourage all of you hard workers to lighten your load and practice these helpful tips to make your own life a tad easier. Stop stressing about speaking to your employer, and start making your way as an adult in the workplace. You’ll feel better, your boss will like you more, and taking responsibility will depict you as a leader. Who knows? A promotion might be in your future.

Sources: Harvard Business Review

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By Sarah White from Miss Millennia Magazine

Read the original article in Miss Millennia Magazine. Copyright 2016. Miss Millennia Magazine is an online Lifestyle ezine for women in their 20’s and 30’s who are transitioning into adulthood. Follow Miss Millennia Magazine on Twitter and Instagram.

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