How to Have a Difficult Conversation With Your Boss


Raising an awkward or uncomfortable topic with your boss is never a fun thing to do, but it is often a necessary evil. Knowing how to do it and the best way to approach it is the key to having a successful conversation. Whether you are asking for a raise, asking for vacation time during a busy season, or have something else important yet awkward to discuss, you need to approach the situation with respect and class.

  • Choose an appropriate time to talk. It is crucial that if you are going to have an important conversation with your boss that you do it at the right time. For example, if you work in retail, you don't want to approach the boss at your store's busy time of day. Look for times when it is slower and you will have time to focus on the conversation at hand. If you work in an office setting, it may be a great idea to actually schedule an appointment with your boss or supervisor so she may prepare for the meeting and have time set aside for it.

  • Plan out your conversation. For a difficult conversation, know ahead of time what you want to address. Plan out what you need to say, how it needs to be said, and consider possible responses your boss may have. The more prepared you are, the smoother the conversation will go. Take notes on what you want to address and use the list during your conversation.

  • Get to the point. When it comes to actually sitting down and speaking with your boss, you need to be direct and get right to the issue at hand. This is not a time to beat around the bush. You need to let him know what the problem is, so that he can understand and deal with it. Being honest and direct with your supervisor makes the most of your time and efforts. It also avoids uncomfortable small talk that can makes the situation more tense.

  • Accept the outcome. No matter how the conversation goes, you must remember, you are not the one who is making the decisions. Whether it goes in your favor or not, you need to accept it and move on.

Related Searches


  • Photo Credit tired boss image by Marin Conic from
Promoted By Zergnet


You May Also Like

Related Searches

Check It Out

3 Day-to-Night Outfits for the Work Week

Is DIY in your DNA? Become part of our maker community.
Submit Your Work!