3 Steps To Help You Prepare For Difficult Conversations

Confidence, Leadership Coaching, Life Coaching, Overcoming Fear, Reducing Stress
09/19/22 - Betsy Westhoff
two people talking to each other at a table

Why is it so simple to avoid difficult conversations? We are SUPER uncomfortable with conflict. We don’t want to come across as mean, opinionated, or stubborn.  Sometimes we are not even sure we have the authority or are right. And so, we get comfortable avoiding conflict. We convince ourselves that living with the status quo is easier or good enough. But then time goes by, and the un-resolved issues persist, disrupting our productivity and negatively influencing our behavior. At work having these seemingly charged conversations can feel particularly challenging. Though we have a sense that tough situations will improve with honest dialogue, it may feel like there is too much at stake to risk the emotion and drama we anticipate.  

Much research has been conducted making it clear that conflict, when handled carefully, can show us new ways to work with others, minimize the risk of having new issues arise, and generate more creative ideas. We’ve all had that feeling where we “swallow” a grievance, begin to make false assumptions about another person, and carry our resentment into the future. It feels like a heavyweight at best and is counterproductive.

There are 3 ways to prepare for having difficult conversations that can build your confidence and lead to results that will be beneficial to all. It isn’t easy work but it’s important.

  1. Decide what a positive outcome from the conversation will be.

In most cases the outcome of a difficult conversation is greater understanding between both individuals. From this place of understanding and reduced tension next steps can be clarified and agreed to. To anticipate what a positive outcome for you might be you can ask yourself questions like:

  • What am I likely not to know about what is driving this person’s behavior or action?
  • What is my role in this situation?  
  • What information are we interpreting differently, and why?
  • If we were able to get to a calmer and clearer place what would be different for each of us? 

This is a great time to imagine how this conversation could go. Take some time to remember what it means to bring your best listening skills with you. Remind yourself what it feels like when someone comes to a conversation, prepared to listen whole heartedly to what you have to say – How can you do that for someone else? 

  1. Declare your intention out-loud.

This is an important step in getting clear about your intentions, clarifying your emotions and practicing. It will require some vulnerability on your part. You may want to tell the other person (a trusted co-worker, friend or coach) your perception of how you got to this place, what presumptions you feel you are making, what emotions are being triggered for you and what you are concerned may get in the way of having this conversation. Challenge yourself to tell this trusted person what is at stake if you do not have the conversation.

For many, writing their thoughts before having the conversation is productive. If that is you, go for it!

  1. Finding the Gem

What is one thing the two of you can agree on?  

I am working with a client who needs to have a difficult conversation with a direct report who is new to the company. The new team member is a critical hire, and the entire team is excited to have her bring her experience and expertise to the organization. Though the team has a flex policy about working hours, there are expectations of clear communication around availability. The new person has been asked to share her calendar several times but has failed to do so and is often not available when others need her. 

In planning for a difficult conversation my client was able to find this gem: “I can tell you care a lot about adding value to our team, and that means a lot to all of us.” She shared the Gem statement with her team member right off the bat. She told me she instantly felt like the energy in the room shifted from high anxiety and expectation to something much more like shared anticipation. During the brief conversation she learned that her new team member had a child suffering “school anxiety” resulting in many unanticipated calls for early pick-ups that were disruptive several times per week. Her direct report acknowledged that she was concerned about her absences but could not come up with a better plan to manage her personal and professional commitments. While she became a bit emotional, at the end she thanked my client for her clarity and concern. The two agreed to stay in closer communication until things settled into more of a rhythm.  

The gem gives you a great starting point for the conversation. To be effective, it must be truthful. Importantly it helps to avoid the “and yet…” That might look like this: “I can tell you care a lot about adding value to our team, and though that is great, the fact that you never tell me where you are is a huge problem.” 

From there, you’ll be ready to practice more related skills so that you can stay present in the conversation, anticipate diversions, and bring conversations to closure. I love this article from Psych that helps with tons of practical detail on this and more.


Building confidence to have difficult but important conversations is a skill that can be practiced. Once you have a clear objective formulating a game plan will become much simpler. Working with a leadership coach is a great way to understand how your own emotions may get in the way as you formulate and practice your plan.

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