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6 Tips for Having Difficult Conversations

Three people sitting in a circle, photo shows only their torsos. Green overlay with blog title: 6 Tips for Having Difficult Conversations

Do you love to have tough but necessary conversations? Let me ask you this—have you avoided having a tough but necessary conversation until it became a more significant issue?  


I may have already known your answer—but I had to ask anyway to drive the point home. It's uncomfortable for many of us to have a crucial conversation with our boss, colleague, co-worker, friend, or even our partners. I know and have mangled many conversations in my career. Each time I did it wrong, I learned something, and over many years of mistakes, I made myself get comfortable being uncomfortable.


I also read everything I could get my hands on regarding having tough conversations. My favorite book on this topic is Crucial Conversations – Tools for Talking When Stakes Are High. The authors defined a crucial conversation as anything high-stakes, with differing views, and where the topic will evoke strong emotions. If you want an excellent guide, pick up this book—it's filled with tips to help you. There are even courses you can take with your teams so everyone understands the principles.


From my study on this topic and my own experience, I have found a few tips that will help you the next time you need to have "a talk" with someone:

  1. Seek First to Understand – I like to get to the crux of the issue and learn more about the players, where they are coming from, and why this is causing strong reactions or emotions. I often ask, "Help me understand." Notice I am not accusing or sharing an opinion—I want to understand first.

  2. Build Trust – When you have a good relationship with someone and trust that both of you want a positive outcome, the conversation goes more smoothly. Trust is built over time and is about consistency. People will trust you if you walk the walk and talk the talk–CONSISTENTLY.

  3. Assume Positive Intent – Always assume that the actions of others are done with positive intent. If we adopt this attitude, we can move to solutions much quicker. Do NOT play the blame game, finger point, or gossip. That negative approach is a time suck and not at all productive. Stay above the fray.

  4. Do Not Sugarcoat the Message – I see many newer managers tip-toe around the issue. They are afraid to be direct—instead, they water down the message with lots of other details and niceties, and the message gets lost. Or worse, the person focuses on the wrong items or hears what they want to hear. Be clear and provide the facts. Brene Brown said in her book Dare to Lead, "Clear is kind. Unclear is unkind."  

  5. Create a Feedback Culture – Create a safe space for conversations, dialogues, and discussions. If people feel safe, valued, and heard, it will be easier to manage those situations or issues when they arise. After a conversation with someone, I like to check in with that person a day later to ask if they had any additional thoughts or ideas since we last spoke. Many people need time to process, so I give them that space.  

  6. Be Brave – I know it's challenging to have these conversations. It doesn't matter if you initiate the conversation or receive the information—acknowledge that it is not easy—and do it anyway. If your knees or voice shake a little, that's OK—do it anyway. If you need to take a few deep breaths to calm yourself—do it. If you need to write out your notes in advance so you don't miss something—do it. Muster up all the emotional courage and do it.  


Life is too messy not to have issues, challenges, and mistakes. That's just reality. It's what we do and how we decide to manage the conversations that matter. It's so easy to find fault, finger point, and place blame—and it seems like that has become our norm. But what if we were all a little more brave, a little more upbeat, a little more clear, a little more respectful, and a little more kind? What would that do to our relationships at work and at home? Let's find out!


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