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  • Writer's pictureShandy Welch

How to Prepare For and Have Difficult Conversations

Updated: May 9, 2023




Out of all the topics that come up in coaching, this has to be number one. No matter your profession, education level, or title, having difficult conversations is a dreaded subject.


Let’s break it down and see if we can make it a bit easier. While this is a big topic, and certainly, there is more depth to be found, this will get you started.


  1. Timing is everything:

    • Emotions will derail you and sabotage the conversation 100% of the time. Step back and give yourself the gift of space and time.

    • If you are committed to having a good outcome, make sure the timing of this discussion is one in which you are not outwardly angry, have the ability to be open to another’s perspective, are interested in listening to learn, and are curious as to what you may not know.

    • Your mindset is critical for success. The goal is to approach these discussions with clarity, calm, and focus.

  2. Be clear on your intention: What do you want from this conversation? To be heard and understood? To be vindicated? To get something or find a resolution? Whatever it is, take time to become clear as to what is your endpoint and what success looks like.

  3. Ask for the time to discuss. Do not blindside your opponent. This will ensure defensiveness and emotion. Ask for a convenient time and place that feels emotionally and physically safe.

  4. Begin the conversation with your shared belief, feeling, or desire: This initial statement will show empathy and brings levity to mounting anxiety. Allowing you both to see the human side of each other immediately diffuses tension and emotion. For example, “I appreciate that we both share the common desire to push this project to completion before next week. It is because of this common goal that I want to have this conversation.”

  5. Be honest, clear, and succinct:

    • When stress and anxiety are high, many people speak louder, take on a quicker pace, and become overly verbose.

    • Take moments to breathe and allow for silence.

    • Pick your words carefully to clearly communicate what you need or want, and then stop.

    • Many of us like to drive the point home over and over, to avoid this trap. Say it once, and then move on.

    • Do not exaggerate and stick to the facts. The words “never” and “always” should be avoided. The other person will seek a reason to discredit your message and disengage. Using these words gives them permission to do just that.


Avoiding difficult conversations only gives you temporary relief, it is never a solution and certainly creates an opportunity for mounting anxiety, and you become a prisoner to the story. Having relationships that are built on trust and honesty are incredibly valuable and rewarding. Well worth the difficult conversation. Be brave and do it.



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