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Having Difficult Conversations

  • Greg White
  • Feb 23
  • 5 min read

Updated: Mar 30


Is there some unspoken truth in your relationship that is causing you distress? Are you hoping that the issue will resolve itself without having to say anything? Maybe you know that you need to say something to that person, but you’re unsure how.


As much as we’d like to avoid them, difficult conversations are an inevitable aspect of life. In these moments, the pain of withholding our genuine thoughts and feelings becomes greater than the cost of speaking them. These times might include telling your partner you want to end your relationship, informing a coworker that their lack of accountability is creating stress in the workplace, giving a friend honest feedback about how their comments at the dinner party impacted you, or letting your family know why you won’t be coming home for the holidays. 


There are several reasons that help explain why we struggle with speaking our truth. Some people have learned through childhood experiences that it is unsafe to disagree or assert themselves. Perhaps they were shamed when they shared their feelings or had their boundaries repeatedly ignored. They may have been labelled as selfish or ungrateful when they expressed their needs, so they learned to keep them inside to avoid scorn and judgement.  


Some people withhold because the important people in their life were emotionally fragile. They may have had a volatile caregiver who was unable to tolerate challenging emotions. Sometimes parents weaponize their guilt to ensure the conversation remains focused on their struggle at the expense of their child’s. These children then grow up to become adults who withhold certain aspects of who they are in order to keep the peace with those around them. 


Whatever the reason someone has trouble speaking their truth, there are steps we take to make having that difficult conversation a bit easier. Here are a few things to keep in mind before you have that tough talk. 


Begin by getting clear on why you’re having the conversation. Why is it important to you to share this information with the other person? What kind of change are you after? Are you seeking to be understood? Are you looking for a specific outcome? Knowing what you hope to achieve will help increase the likelihood that it will occur. 


Next, write down the key points of the message you’d like to convey. Are there examples that might help provide clarity for the other person? In the heat of the moment, it’s easy to forget what we planned on saying. Writing down and even rehearsing your message will help you stay on track when it’s time. If you find it helpful, you might want to consider practicing this conversation with someone you trust before having it with the intended person. 


Once you’re clear on why you’re having the conversation and you’ve thought about what you’d like to say, check-in with yourself. How are you feeling? What sensations are occurring in your body? It’s normal to feel a certain degree of stress in these scenarios. If, however, the thought of having this talk feels overwhelming, perhaps you might want to wait until you feel settled enough before engaging. 


If it’s helpful, try imagining how this conversation might go well. Can you visualize you and the other person engaged in respectful dialogue? Is it possible that this conversation might bring you two closer together? Can you imagine how much lighter you’ll feel once you finally take this weight off your shoulders that you’ve been carrying for so long? 


When you feel ready to engage, select a time and place to have the conversation. Consider issues such as privacy and what other stressors may be occurring for you and the other person. There might never be a perfect moment to have this talk, but there are times that may be better or worse. 


If you’re wondering how you might initiate a conversation, a few options could be:



I’d like to talk to you about  ____________ and I’d like to hear where you’re coming from. Do you have some time this week to chat?


I’ve been meaning to talk to you about  ____________ and I’m really curious to hear your perspective. Could we go for a walk together? 


I need your help in getting to the root of this struggle we’re involved in. Do you have some time to talk? 



Once you meet with the other person, try opening with some form of gratitude. You can thank the other person for their time and share whatever you genuinely appreciate about them. This could be followed with some kind of request for assistance to work together. An example might be:



Thank you so much for meeting with me today. I appreciate the connection we have and I’m wondering if you’d be able to help me work through something I’ve been thinking a lot about. 



What’s important is to establish a foundation of respect and collaboration from the onset. Even if aggression and blame feel warranted, these tactics will likely cause the other person to react defensively or shut down. When we feel as if we’re under attack, hearing another’s perspective becomes challenging. When describing a situation, take ownership of your own feelings instead of passing judgement on to the other person’s behaviour. An example might be:



At the dinner party the other day, I was really embarrassed after you made that joke about me in front of my friends. It’s a sensitive issue for me and when everyone laughed, I felt small and alone. 



Once you’ve voiced how you've felt and expressed any changes you’d like to see, provide space for the other person to share their view and feelings without interruption. It’s very likely they have a different perspective of the situation and your words may come as a surprise. You don’t have to agree with them, but try to understand the underlying reasons behind the other person’s words and actions. When people feel as if their feelings are acknowledged and understood, they are more likely to work with us in meeting our needs. 


If the other person expresses criticism, consider how you can remain grounded. This might include pausing before you respond to take a breath. What questions might you ask that would help the other person express what they think and feel? Genuine curiosity is often a powerful antidote to hostility. 


After the conversation has ended, check-in with yourself once again. What sensations do you feel? Is there any energy in your body that wants to move? Do you need to go for a walk, have a bath, eat a meal, or write in your journal? 


Difficult conversations are uncomfortable, but they’re also clarifying. When we withhold our truth, we prevent those around us from understanding who we truly are. Our fears about how others might react causes us to act in ways that aren’t reflective of our truest self. In this way, we become disconnected from who we are. Having the tough talk is an act of courage. It’s acknowledging what isn’t working and bravely stepping towards a more fulfilling path. It might even lead to a deeper and more genuine connection, both with yourself and the other person.

 
 
 

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I live, work, and play on the traditional and unceded territories of the Sinixt, Ktunaxa, and Sylix peoples. As an uninvited guest on this land, I extend deep gratitude to its past and present caretakers.

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