Having Constructive Difficult Conversations

Two friends talking together having a difficult conversation
Photo by Korney Violin / Unsplash

Too often we hold ourselves back in life out of fear of having difficult conversations.  Consistently we choose that it is easier to not have the tough conversation because it suppresses the risk of rejection, failure, social pressure, and vulnerability.  However, not only is it liberating, but it also will allow you to have a more fruitful relationship.

What If You Vocalized Your True Thoughts

This is the big question that parallelizes us all: "What if".  You never know how someone will respond to an honest and intimate conversation.  With this uncertainty, we instinctively ask ourselves questions like:

  • What if I hurt the other person's feelings?
  • What if they become angry with me?
  • What if I damage the relationship?

These are honest and rational concerns.  Unfortunately, our thoughts are quick to conjure up the bad. Our human nature would rather avoid a negative than gain an equal positive. This concept is known as "Loss aversion".  With this principle in mind, let's replace these "what if's" with the devil's advocate arguments.

  • What if I shared the truth no one would tell them?
  • What if I could have saved this relationship?
  • What if I could have built a friendship?
  • What if the conversation led to a new breakthrough or idea?

It's good to remember that there are always "What if's" that are both good and bad.

Why Should You Have Difficult Conversations

I believe having hard conversations is akin to pruning a tree.  It allows us to remove unhealthy branches, it's a treatment that prevents future disease, and it promotes new growth.

When we come to the conversation with humility and truth, the process allows us to identify and verbalize "unhealthy branches".  These are things in our life or relationship that we can agree need to change.  Similar to the well-known A. A. principle, until we admit we have a problem there is unlikely to be any change.

When we don't communicate we are more likely to hold internal resentment and stress towards a situation or another person.  A healthy conversation is similar to a treatment that prevents future disease.  This is manifested in your personal life through removing tension, limiting regrets, and being at peace knowing you have done all you can.

Lastly, when we prune we allow for new growth.  You will experience personal growth when you have difficult conversations as the process will push you past your level of comfort.  Our minds and bodies do not grow unless there is a significant driving stimulus.  Additionally, there is an opportunity for trust to be built and the relationship to grow.

You don't want to live in regret that you were unwilling to have the conversation you knew was needed.

How Do We Have The Conversation?

I know what it feels like to want to avoid a hard conversation hoping the problem will go away. I can tell you from experience it's not going to. Once I figured this out, I now actively choose to take the plunge into a hard conversation and the principle continues to prove its worth.

A man jumping into a lake from a rope swing representing "Taking the plunge" into a difficult conversation
Photo by Blake Wheeler / Unsplash

The ingredients to having a difficult conversation are:

  • Brief Preparation
  • A two-way conversation (with humility and grace)
  • Problem Solving Or Boundary

Brief Preparation

Before having the conversation, I would recommend answering the question "What specifically is frustrating me?"  This is a perfect starting place because it's critical that you have an accurate understanding of the cause so that you can solve the right problem together.  In addition, I would think about "What are some ways we could solve this?"  Once you have the answers to these two questions I would have the conversation.  Do not dwell on your arguments longer or you risk your conversation being interpreted as an assault.

A Two Way Conversation

When you begin the discussion it's important that you focus on having an honest and humble two-way conversation.  Speak openly about your thoughts and ensure you listen graciously to theirs.  Seek to understand and refrain from lecturing, berating, or guilting the other person.  Do not hasten to move on until both parties fully understand each other.

Problem Solving Or Boundary

Finally, discuss what future actions will look like.  The nature of the conversation will either lead to cooperative problem-solving or you setting a boundary.  Sometimes difficult conversations lead to the creation of a boundary in which you draw a line to protect yourself.  If you need help understanding how and when to create Boundaries I would highly recommend the book Boundaries by Dr. Henry Cloud and Dr. John Townsend.

Hard conversations may not end with the outcome you want, yet they allow you to identify what needs to change, they create new growth in your life, and they bring you peace.


I'd love to hear from you about your experience putting these principles into action.  Send me a message here.