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Having the Hard Conversations

Having the Hard Conversations

By Kaitlin Costarene

Whether we like it or not, having hard conversations is a part of life. Having difficult conversations has always been challenging for me. Regardless of what it may be about, when a conversation feels difficult, it usually involves vulnerability and/or confrontation. It can be challenging or uncomfortable to be vulnerable or confrontational, but sometimes, doing so works in our favor. 


Last week I read something posted on an Instagram account called “We’re Not Really Strangers.” The post provided tips on how to have a hard conversation. It felt so honest, compelling, and simple. I’d like to share some of the main ideas with you below in hopes that it resonates with you in some way:


  1. Showing up imperfectly is better than not showing up at all.

  2. Conflicts are often fueled by miscommunication more than anything else, so be clear on what you mean.

  3. Replace judgement with curiosity, as this often changes an argument into a conversation.

  4. Allow room for silence. It will help you process and give the other person the opportunity to finish their thought. 

  5. If you find yourself getting defensive, ask yourself why.

  6. Find the important similarities between your perspectives whenever possible.

  7. Rephrase what the other person said to make sure you really understood their perspective.

  8. Know when it’s time to step away from a hard conversation. If the other person is not making an effort or is being condescending, check out.

  9. Sometimes the hard conversation needs to start with yourself.


Each of these ideas holds a significant value to me, and they can be interpreted in a number of ways. That might mean something different for everyone, but generally speaking, this quick list on how to have a hard conversation is both helpful and encouraging. 


Hard conversations, while difficult in the moment, are often rewarding. Your perspective may be challenged and you may get upset, but hopefully you will also be able to identify the issue at hand and work to resolve it. Then, you will grow. A conversation with a difficult person can be challenging. A conversation about a difficult topic can also be challenging. Both of these are going to happen throughout your life, and during those times, it is more important than ever to be open-minded and to listen. On a number of occasions, I have had conversations with someone who refuses to acknowledge another perspective. In this scenario, the conversation, or lack thereof, is ineffective. When two people cannot listen to each other, remain calm, and respect one another, there is no conversation to be had. I encourage you to be as patient as possible when dealing with people like this, but to also know when it is time for you to step away. In my own reflections, I have been able to turn inward and evaluate myself on my ability to stay open-minded and to truly listen to opposing viewpoints that are presented to me. These are now qualities that I make an effort to prioritize, and also some that I look for in others. I’ve also had conversations that are about difficult subjects, during which I struggle to articulate and express everything on my mind. For those of you who do not have a hard time with this, I applaud you. For the rest of us, we must remember that being open and honest is the only way to get what we need out of the conversation.


With that in mind, I hope this list of ideas gives you some peace of mind and encouragement. Hopefully now you will be better equipped for the next “hard conversation” you find yourself having. 

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