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Are you avoiding Difficult Conversations?

Updated: Feb 4, 2020

Are you avoiding Difficult Conversations?

Three Reasons We Avoid Difficult Conversations and How to Face Them

I often ask my clients, “Why do you think your teams avoid difficult conversations?” Here are a few of the responses from leading executives, and my take on how we can overcome these challenges.

1) Alex, VP

“Using hope as a strategy”

Alex says hope as a strategy promises a resolved future without the necessity of conflict. The truth is conflict may arise in any situation, and they do not get better on their own. An avoidant stress/communication response is one of the four communication styles that we discuss in our personality style course. There is a positive of an avoidant style: They usually support and go with the flow when there is conflict. The downside is they can have a tendency to a “flight” response which can play out in many different ways (ie. using hope as a strategy, telling ourselves it’s not that important, downplaying our feelings, etc). Studies have shown us that less than half the situations that people assume will be difficult actually turn out that way.

If this avoidant response resonates with you, then try to keep in mind the quote by activist and author, James Baldwin. “All things that are faced can’t be changed, but nothing can be changed until it's faced.”

2) Drew, Founder says “Sometimes I feel the risks of having the conversation, don’t outweigh the benefits. Even if I do, I don’t believe that they will change.”

It may be true that in some instances the best decision is to let the issue go. Communication is both an art and a science and this is more of the art of taking into account the context and situation. I also agree it also takes personal awareness and motivation to change behavior. That being said, our assumptions can hold us back because we are not allowing the situation to unfold or the other person to tell their story. Especially if you consider yourself a leader, these are the conversations that we must have. Outside of the occasional cultural misfit, my clients have walked away from difficult conversations feeling more confident, at ease, understood, and clear about the appropriate ways of interacting moving forward.

3) Mario, Head of Global Banking

“I worry that I will crush someone’s self-esteem or they will lose respect for me if I give them bad feedback.”

My belief is that by giving balanced feedback you are giving a “gift” to the other person. It also matters about the relationship and context of the two people. Many people are not ok with unsolicited feedback. We practice the 2X2 feedback model: Two things someone did well and two things they can improve. A motto we use in our programs and as we give each other feedback during the exercises is “if you only tell someone what they did well and don’t balance that with what they can improve, then you are doing a disservice to yourself and to the person you are working with.” It’s a shift from being “nice” to being “kind”.

The good news is, it doesn’t take a long time to misplace these lifelong habits and stress responses. These issues and many more not mentioned are what we work with clients on and help them overcome through workshops and coaching. One at a time, we are equipping individuals and organizations with skills to create cultures of deeper understanding, courage, open communication, productive conflict, and the ability to grow.

No matter what your reason may be for not having a difficult conversation, here are some tips for you to consider:


The first step to removing the barriers to difficult conversations is self-examination. This is your opportunity to take responsibility for your thoughts, feelings, and role in the situation. After you have taken inventory within yourself, you’ll be better prepared and centered to talk to the other person. Before a difficult conversation, take 5-10 minutes to reflect and answer the bullet points below:

Schedule time. Don’t make the difficult conversation impromptu or in between meetings. A scheduled time sets aside the time for the conversation to unfold.

Your intent. Please don’t start your conversation out of the gate with your concern! Instead, think about, “How will this conversation will benefit you both?” This might be the most important question to answer.

An appreciation. There is always something you can appreciate even with the person in conflict. Make it authentic, or don’t use it at all.

Be succinct with your concern. Get to the point. Beating around the bush can cause confusion about what is the actual concern.

This preparation and the actual dialogue takes practice. Practice with a friend, and better yet, practice with a coach that can support you with the most difficult form of communication.

Join me for an upcoming training to learn more about these tips and other tools that will help you succeed through your next challenging conversations:

The Art of Productive Conflict on February 29th, 2020 | 10:00 am - 3:30 pm

In this all-day workshop, Jared Dickinson will coach a small group on the tools for dealing with interactions of all kinds. These may include challenging interactions where disagreement and conflict are present or any exchange that could benefit from good listening and responsiveness.

Register here:

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