How To Have Difficult Conversations With Your Boss

  • Posted by Steve Goldberg
  • |
  • June 19, 2015
difficult conversations with your boss

Difficult conversations are never easy to have, but are especially difficult to have with your supervisor. Digital Media and Media Technology is a fast-paced, high intensity environment, and solid relationships with your supervisor(s) are essential for your own success and the prosperity of the organization.

Sometimes when there is a possible conflict, it’s all in our head, and other times it’s because there is a communication disconnect. Either way, it’s best to prepare and approach with tact. Below are some tactics one can utilize when approaching difficult conversations with your boss.

“Check Yourself, Before You Wreck Yourself”

Often times approaching a difficult conversation can be harder when your mindset isn’t in the right place. Going into a conversation with a hostile or confrontational attitude, expecting there to be a winner and a loser, can have a significant impact on the progression on the conversation—word choices, demeanor, and your body language can result in a less-than-desirable outcome. So approach all conversations with a sense of self-awareness – check your attitude at the door, and always be level headed.

One practice described in Psychology Today is to “find a quiet spot and a quiet moment, sit down and write an unedited letter to the person with whom you need to have the difficult conversation.”  You are not going to send it…it is just to get your raw feelings out.  Then, read the letter as if you’re receiving it – put yourself in their “shoes”.  This process will help reduce the strength of the emotions, so that when you have the conversation, you can deal more effectively with the situation.


Whatever the issue is, make sure you have respect for your boss and respect for yourself. These are perspectives to hold always in all situations anyway.  Even if you feel you could do your supervisors job better than he/she can, always remember to respect their authority. This will also help you keep your attitude in check. Additionally, if you are going to speak to your boss about a specific situation, know that he/she may know more background information than you realize. They could have their reasons for withholding information about a given circumstance.

Articulate Your Needs

Ask yourself, “What do I need?” It’s best to make sure you’re easily able to articulate exactly what you want out of a conversation in an intelligent and thoughtful way, without getting caught up in the moment. Your supervisor will not only respect you more, but also be better equipped to help you.

Make sure your needs have some relationship with the “greater good” of the department or organization as a whole.  You want to be a team player and contribute more to the organization, or make a change.  Can you create a context whereby this is also what is best for all?

Remain Even-Keeled At All Times

Sometimes conversations can elevate in intensity, which you should try to avoid.  There are times that your conversation counterpart may not always remain level-headed.  But it’s imperative, in combination with all the above, to remain even-keeled as much as possible during the conversation. At the end of the day, your supervisor may lose their head, but the situation can easily be turned against you if you respond in kind.