life coach & mentor


Having Difficult Conversations

December 4, 2022

Earlier this week, I was watching a trashy reality TV show on Netflix. I will not tell you which one, but needless to say it involved real estate in Beverly Hills. In one scene, one of the lead women in her early 30s was describing to a friend how she had been dating the same guy for 4 years, but he hadn’t proposed. She, however, was feeling that it was time to marry and have babies. Fine. Then she went on to say that she had not had this conversation with her boyfriend. She had no idea what he was thinking about these issues or how he felt! So I wanted to share a few ideas that may help you when having difficult conversations.

My immediate reaction to her admission was to cringe inwardly, wondering what she was thinking. She then went on to say that she hadn’t had that conversation with him. She was afraid of what he might say. Fair enough. We’ve all been there. Especially in relationships with a significant other, where we don’t want to jeopardise what we currently have. Instead we just keep hoping for the best. This can also happen at work or with our parents, etc. We let our fear of the worst case scenario occurring keep us from having the difficult discussions. We don’t ask for what we want.

This, of course, makes sense. Our brain is trying to keep us safe and in order to prevent us from feeling vulnerable, disappointed, or sad (or insert whatever emotion comes to mind for you). It keeps us in a state of fear. The more fearful we are, the less likely we are to have that conversation, the less likely we are to experience the emotion we don’t want to feel.

I wanted to ask this woman if it wasn’t better to have this conversation with him to find out what he was thinking. Then she could decide if she wanted to stay with him or not. In a following scene, she did actually bring up the subject to him. But the way she did it was in a very vague sort of way. Then his answer was even more vague. It was truly awkward. I think the conclusion was that he just wanted to see how things would go and he was very non-committal.

Having that difficult conversation

So, how do we work up the courage to have the difficult conversation and ask directly for what we want?

First, we want to have awareness around what we are afraid will happen. Specifically, what we are afraid of feeling. For instance, our friend in Beverly Hills, was afraid her boyfriend wouldn’t want marriage. She would then feel disappointment, rejection, and sadness. This is important to know. She might also be afraid that she would have to end the relationship or that he would. Also important to know. She would then think that she would be alone and might either never find anyone else.

Oftentimes, our brain offers us this vague yet overwhelming feeling of fear, but we don’t want to explore the fear as to what exactly it is afraid might happen. Understanding the specifics is an important first step to overcoming the fear.

Next, you need to be clear, that regardless of whatever happens, you are afraid of feeling that emotion you think will accompany it. So, in this instance, she was afraid of feeling rejected. The good news is that you can experience any emotion and you’ll survive. That’s not to say it will be easy, but feeling an emotion won’t kill us. We can do it. And if we can process the emotion – meaning we allow for it and feel it without trying to change it or resist it, then we can move through it quicker.

Reassure yourself that regardless of how you end up feeling, you will be OK. It’s just an emotion and you can feel any emotion and survive.

Explore the Best and Worst Case Scenarios

Our brain loves to offer us the worst case scenario. It will tell us we’ll have the conversation with the boyfriend and discover he doesn’t want to marry her. The relationship ends.

And that may be true.

But if there is a worst case scenario, then that means there is a best case scenario. We could have the conversation and he might want to get married and have children too.

We need to give equal airtime to both cases – worst and best. But in order to do so, we need to deliberately ask our brain to focus and imagine the best case.

The next time you are finding yourself going down the worst-case scenario path, ask your brain for the best case scenario. Spend some time there imaging the details and how that would feel.

Know Your Why and Like Your Reasons

When you want something and need to have a discussion about it with someone, it helps be very clear about why you want it and that you like your reasons. You want to be clear and confident in your own mind first. When you have this information, you will show up differently for the conversation. This clarity will give you strength and determination that will translate into positive action. Even if the conversation doesn’t go exactly as you had hoped, when you are clear about what you want, you will be able to think rationally about next steps.

Preparing for Next Steps

Preparing for next steps is not about ultimatums. Ultimatums are never the answer. However, you want to be clear about what you will do if you don’t get what you want.

If, for instance, in Beverly Hills, she has this conversation with her boyfriend and he says he doesn’t want to get married. She needs to be clear then what she will do. There is no need to tell him she will leave if he doesn’t marry her. She decides she will leave. Or not. But it’s good to think about this ahead of time. There is no right answer here for her, except what she wants. She decides what she wants and she doesn’t need to explain it or justify it to anyone. But, for her, it means that she keeps her power. She actively decides what she wants to do, but at least know she has more / better information.

When You Are Ready to Have the Difficult Conversation

When you are ready to have the conversation,

  • choose your thoughts about the conversation and the other person deliberately. Thinking that you either you don’t want to deal with them or that it could be an ugly conversation, will not be helpful and you will show up for the conversation accordingly.
  • be honest with the person you are speaking to about how you are feeling. If you are feeling a little afraid or nervous, share that with him/her.
  • allow for them to have their opinions and feelings.
  • be curious and be open to receiving their true opinion, whatever it may be.
  • try to understand their position and why they might be feeling the way they are and have compassion for them.
  • remember it takes two people to argue. The other person can be upset but it does not mean that you have to be.
  • approach it as an opportunity to connect and develop intimacy with them.
  • if the conversation becomes too heated, ask for some time as a break to calm down and collect your thoughts. Resume the conversation when you know what you want to say and the other person is ready too.

Having difficult conversations is a part of life. But with some preparation, curiosity and compassion, the conversation can be easier than you think. The important thing is to be honest with yourself and with the other person and hold space for yourself and them to express emotions and have opinions.

Most importantly, having difficult conversations requires you to allow yourself to feel whatever emotions you may be afraid of. Know that regardless of what emotions come up, you can feel it and survive it. It will not kill you. A feeling is just a vibration in your body. Most likely, the conversation will not be as bad as you imagine and you will feel better afterward. And there is freedom in resolving issues that will help you to move forward with your life, when you know the other person’s position and have decided accordingly how you want to proceed.

If you want help in having difficult conversations, I offer private one hour coaching sessions. You can schedule yours HERE.

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