What makes something a difficult conversation will depend on the people involved, their relationship, the power dynamic, and the trust they have between them. For most, a difficult conversation is one where there is a potential for conflict. For example:

  • Telling someone no / hearing no from someone
  • Sharing feedback with someone / hearing feedback from someone
  • Telling someone they hurt you / hearing that you hurt someone
  • Saying that you disagree / hearing that someone disagree with you
  • Apologizing / receiving an apology
  • Confronting racism, bias, discrimination, and/or microaggressions

Getting comfortable with such conversations takes practice. Even if you have years of practice, having such a conversation with someone new can make the conversation feel hard all over again. And while each situation is different, following these steps usually leads to a healthy, productive outcome. Keep in mind that the steps for “initiator” and “listener” sometimes happen simultaneously at certain points, as illustrated in the table.

As the initiator...As the listener...
Prepare. Understand your own feelings first. Were you triggered? What else is going on? Make sure you understand as much as you can about where you are at, why the conversation is important to you, what you want to get out of it, and what you want the other person to get out of it. Taking time to write out your script for approaching the conversation can be helpful. It can also be helpful to talk with someone to help you process. 
Practice or review. Either practice your script to get more comfortable saying what you need to say or review it with someone you trust. 
Make sure you are ready to have the conversation and that you feel truly okay having it. If you are still reacting, it’s okay to take time to feel what you feel. It’s also okay to seek help if you need it. 
Try to gauge whether now is a good time to have the conversation. If you are aware that it might not be, it's okay to wait. Timely doesn't mean instant. Timely means within a week or so of whatever happened to require the conversation. 
Share and seek context/understanding/resolution. Share how you have been impacted and share what you seek. A helpful “template” is: “When you ____, the impact was ____. I’d like to understand/I’d like it if we could do ___ differently/This is what I need to heal from this...” The exact format will vary on the situation.  
 Listen, listen, listen. In difficult conversations, our fight, flight, or freeze instinct often kicks in. Recognize this and if you need time before responding, say that. If you are not able to listen with grace and respond with grace, simply say “Thank you for your vulnerability in bringing this to my attention. I need some time to process this. Can we resume our conversation _____.”
 Allow for emotions. Hard as it is to hear what someone may need to say in these conversations, it is always harder to initiate them. Try to ground yourself in the reality that even if your intention was different, you had an impact and you need to understand it so you can do differently next time.
Be prepared to give space. Sometimes folks need time to process or a little space before they can engage in talking about a resolution.  
 Make sure you understand what was raised to you and make sure the person who raised it knows you understand (this ensures they feel heard). 
 Share what you will do to repair the situation, being sure to include what the other person shared they feel they need toward resolution
Work toward resolution with those involved. This can sometimes be easier said than done, but when it’s possible, it will result in the healthiest outcome. 
 Follow-through. Trust can be permanently broken if there is no follow-through. 

Keep in mind that as a leader, if someone initiates such a conversation with you, there was absolutely nothing easy about that. Being secure with yourself and the ability to listen and respond with grace is crucial. These types of conversations are gifts for leaders, and if you react poorly, the initiator may never start a conversation like this again. It is also more than reasonable that if someone initiates such a conversation with you they might skip a few steps. Grant them that and chalk it up to the weight of the power dynamic.

Suggestions for deeper learning

Spend a few hours just searching the internet about any of the ideas presented here. For example, Google any of the following, click into some of the search results, and take it all in:

  • Difficult conversations
  • Actionable feedback
  • How to apologize
  • Calling someone in
  • Accepting feedback
  • Demonstrating accountability
  • Tone policing
  • Confronting racism
  • Confronting bias
  • Confronting discrimination
  • Confronting microaggressions

Make note of anything you discover along the way that particularly resonates with you (you might want to refer back to it later or share it with others -- feel free to do so here in a comment on this course or as a post in Inspire(d)).

Read the following over the next few months:

Reflection/action prompts

  • Reflect on what you have learned about difficult conversations as an initiator and as a listener. Go for a walk, or sit with a beverage of your choice and give your mind some space to just wander and process.
  • If you feel so inclined to share the results of your reflection with the rest of SuperCats, post in Inspire(d).
  • If you have any questions or would like to dig deeper on anything in this course, please post in Get/give advice (remember, it's okay to do so anonymously).


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