General Business

How to Have a Difficult Conversation

Relationships can be messy.  Professional relationships, dating relationships, relations with family, friends, acquaintances, co-workers, your daughter’s ballet instructor, your dog, you get the idea.  There comes a time in all of our meaningful relationships when we have to have a difficult conversation or two.  These conversations can be uncomfortable, emotionally trying, and painful.  Hopefully these conversations can be largely avoided by upfront honesty from all parties involved, but of course this is not often the case.

If you find yourself needing to have a long-procrastinated difficult conversation, here are some questions you should ask yourself and steps you should take before, during, and after that difficult conversation.


What is the source of strife?  Why is this a problem?  It’s amazing how often we blow things out of proportion in our minds.  Are you sure this issue must be difficult?  Have you made false assumptions about how the person will react?  Is it possible they may be more receptive to you than you are expecting? What do you hope the outcome of this conversation will be?

Asking yourself these questions and any others you can think of will help direct the conversation in a constructive way.  Journaling these conversations can be especially helpful.  Try answering them before and then again after the conversation.

Be sure you are not making too many assumptions before going into the conversation.  Conflict resolution is a much easier task when the parties involved don’t feel like they have to be on the defensive.  If you back away from the situation and realize that the person might not be as defensive as you expect, you’ll find that you won’t go into the conversation feeling like you have to be defensive as well.


When you start the conversation, be sure it’s at an appropriate time and place.  Usually this should be fairly obvious: don’t fire an employee in front of co-workers in the break room, don’t end a relationship in between appetizers and the first course, etc.  Ensuring that the conversation takes place in a comfortable and safe environment makes it easier on everyone.


During the conversation, focus on the issue, and keep the issue at the forefront of your conversation.  Don’t attack the person, and don’t make them feel like you are upset with them personally.  Keep the attention on the issue between the two of you that has been a strain.  Hopefully this conversation will not be a complete surprise, but whether it’s expected or not, the person is likely to have questions.  Listen carefully and respond honestly.  It’s best to get everything out at once.


If at all possible, let the person know you still value them.  This area is one where you will especially have to use your own judgment in the context of your unique situation.  Let the person know that you think that you support them and you believe in their ability to have healthy relationships.  Empowering this person is very important since it’s likely that you have been the dominant force in this conversation.

Write about the conversation in a journal so that you will remember exactly what was said, what your feelings were, and what your impressions were about how the conversation was received.  It’s likely that this conversation will be the first – and hardest – of other conversations to follow.  Documenting this one is important so you don’t lose any detail and have a record of what was said in this first confrontation.

Openness and honest communication is key.  Maintaining these things can reduce the amount of difficult conversations in your future.