how to talk to your boss

Best Practices for Awkward Conversations

In your professional life, you’re going to have more awkward conversations than you’d like. An awkward conversation can be one of a bunch of different things. Maybe you want to ask for a promotion! Maybe you need to report inappropriate behavior from a coworker. Whatever your conversation may be, it can be awkward to start it.

Asking for a raise is awkward… but we already wrote that article.

Be Frank, Honest, and Get it Out Quick

There is no sense in beating around the bush about what you need to tell your boss. The more you struggle to get your message out there, the more difficult and awkward it will be.

Give it to your boss bluntly. Tell them what you need, why you need it and wait for their answer. There is an old saying that goes “You’d rather be shot once in the head than four times in the chest.” This is advice commonly given to people who have to fire someone (another awkward conversation). Get your message out, and make sure you are clear.

Talking Tips

If you’re non-confrontational, here are some general tips on speaking to someone:

  • Make eye contact
  • Either stand, or sit straight up
  • Take a few deep breaths beforehand to work out the nerves
  • Get your heart-rate down beforehand in case you are nervous
  • Don’t talk too fast or you’ll fumble over your words
  • Write out what you want to say first

Practice With Someone

If you have a friend, family member or even a coworker that you trust, you can role-play the conversation with them. Speak with them as if they were your boss. Ask them for feedback on how you spoke.

Pick the Right Time to Talk With Them

If your boss is busy, or if this is taking you away from what you should be doing at work, this can go from being awkward, to be annoying for your boss.

Typically, talking at the end of the workday is your best bet. You can also schedule a time with your boss beforehand. Give them an idea of how much time you’ll need, and the two of you will pick a time that works best.

If the Conversation is Very Awkward, Have a Coworker Join You

For matters regarding the personal behavior of a coworker or even your boss themself, you might want to consider bringing a coworker that you trust with you. Along with helping to keep you calm, another person on your side in the conversation can help you keep on point so that you don’t drift off on a subject that doesn’t matter.

If the awkward conversation is regarding something that affects multiple people in the office, you can invite multiple coworkers in on the conversation. Remember, there is strength in numbers!

Get a Set Timeline

The outcome you want from this conversation is some sort of change or different results. No matter what you are asking for, make sure you know when the changes will be made if they are going to be made at all.

For example, if the conversation is about an employee is behaving inappropriately, find out when your boss will talk with said employee so you know when to expect some change in their behavior.

Should You Even Have the Conversation?

Before you even have the conversation with your boss, think about if the conversation is worth having. Talk to some friends, family members and coworkers about the issue and get their feedback.

They may tell you information you were not privy to before that changes everything. It could turn out to be a misunderstanding, or there may be information you learn that makes the conversation null.

For example, a few years ago a coworker of mine was nervous about talking to our boss about the lack of employee parking. He was tired of spending money on ride-share apps and wanted the company to pay for his transportation. What he didn’t know which I was able to tell him was that most of us took the train, which was around the corner from our office. I also showed him the cheapest parking garages nearby, which cost far less than any ride-share app. He was satisfied with the information I gave him, so he did not go through with the conversation.

A little bit of feedback from someone else can make you change your mind entirely.

What if This Doesn’t Work?

If you didn’t get the response that you wanted from your boss, you have other options. You can bring the subject to your HR department, or even your boss’s supervisor.

If you still don’t get the results you needed, it may to time to reflect on whether or not you want to stay at this position. You are doing yourself no favors if you stay with a job that feels toxic or hostile.

If you need help getting ready for the next step in your career, we can help! Check out our online schedule, and get a free consultation to meet with a resume-writing professional!


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