5 Tips for Discussing Important Issues with Your Boss

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Discussing important issues with your boss can feel uncomfortable to say the least. After all, they sign your paychecks (or at least give you the thumbs up for even getting a paycheck!). Over the course of your employment you may be faced with a wide variety of important discussions with your boss. Everything from: going on an extended vacation or leave, to working remotely, to having an issue with a coworker, or being considered for a promotion or new position. Sometimes, the important topic of discussion may even be that you made a major mistake that you need to come clean about or get ahead of.

The last thing you want to do is fumble through your ask or get a big fat “NO” because you weren't ready for the big talk. Failing to have important discussions at work can bring down our overall mood and drive and have a far greater impact on our quality of life than we realize. 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.

TIP 1: Lay the groundwork

Start by thinking ahead. You'll want the lines of communication to be free flowing between you and your boss. Even if he or she is not the nicest, it's important to get off on the right foot. It'll 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?).

Feeling stuck on what to talk about with your boss? 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.

TIP 2: Check your attitude 

DO NOT BE AGGRESSIVE. I repeat, 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. Personally, I like to prep some notes and rehearse at home in order to remove any emotion or aggression from my delivery in advance. Calmly explain your situation without losing your cool. If your boss starts to get a little defensive or negating, maintain your composure. Whining 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.

TIP 3: Prepare for the discussion

Take some time to write out a few notes on what you want to say. A great frame work is to describe the problem and then 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, as long as the details are relevant to why you're bringing up the problem and the solution. No need to callously throw anyone under the bus because you're annoyed.

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).”

Then stay open to the possibility. Maybe your boss will go for your solution, or maybe your boss will have an entirely different idea. The bottom line is to come off as a team player without an agenda. You'll come out looking like gold in most cases if you can do that.

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TIP 4: Take responsibility



Part of navigating important discussions with your boss is to be prepared for the aftermath. Yes, that means accepting responsibility and whatever the consequences may be. Take responsibility for any of your actions. This is especially important if you've made a mistake, even if you think you may get fired, it's may turn better than you expected because of your willingness to own your role. If getting fired is a big fear of yours, remember, it takes time and money to replace an employee, so they'd rather you own your stuff, have a good attitude, and keep working than investing their resources into finding another your.

Firing aside, if your discussing something like vacation time or working remotely, remember that this is not the time to use your personal issues as a reason for why you should get the time off or remote position. Keep those conversations based to the facts (re: tip 3). If your boss gets ugly with you for whatever reason and threatens to fire or penalize you because you too the days you were entitled too and you've run them through the proper channels (e.g. company policy only requires you to clear it with HR, which you did), then maintain your cool (tip 2) and pass the problem off to human resources to deal with.

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TIP 5: Don't shift blame or focus

This one summarizes all the previous points. Whatever the issue is, it's not your co-worker's fault. It's not your bosses problem because you have family stuff going on. It's your responsibility to manage your life. There is no need to make anyone look bad, or guilt or shame someone to achieve your desired outcome. Remember, people may not remember what you say, but they will remember how they feel after you leave the room. Maintain your dignity and office reputation, no matter the situation.

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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