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When is a good time to have a difficult conversation?

by | Oct 16, 2021 | Downside of self-improvement & psychedelics, Featured Posts, Meaningful business, Overcoming self-doubt and fear

My legs were shaking. I could feel my anxiety rising and my breath tightening. I was about to sit down with a friend to have the conversation I’d wanted to have for a while, but everything in me wanted to run away. The thoughts kept coming: “Just keep the peace”, “Don’t bring it up”, “Is this worth it?”

I imagine you can relate; difficult conversations are ‘difficult’ for a reason.

I think difficult conversations are opportunities to communicate with someone on a topic that means a lot to you. This applies to work, home, friends, lovers, and children. The purpose of the conversation is to improve and build strength, trust and resilience in the relationship.

We can’t construct healthy relationships without being able to navigate the uncomfortable conversations. However, in my experience, most people would prefer not to have the difficult conversations and live in the unsaid frustrations or avoid contact all together. Isn’t it sad that it’s commonplace to avoid hard things so that we can bypass discomfort, that we’ll give up the opportunity to grow and make a relationship more special and honest.

When I was growing up, I don’t recall there being anyone in my life who was skilled at having hard and honest conversations. The ones I experienced were often disciplinary and one-sided, with yelling, shaming and blaming. It makes sense that it’s something most of us are uncomfortable with. The experiences from our childhood that left us feeling awful are the ones we want to hide from.

It’s easy to get upset with someone and complain about them behind their backs; tension grows and resentment expands and we play the victim instead of being a co-author of the outcome. However, in EVERY single conflict or frustration there are two equal sides. There is someone with their own experiences and their part of being right in the situation. Not just the part that we want them to be wrong.  

It’s been my life’s BIG work to learn how to have healthy difficult conversations. It’s become a skill that I’m proud of. It’s not that I’m particularly good at those conversations, it’s that I’m willing to get uncomfortable and fumble through myself to have them. I’ve experienced very few people who are willing to step into the arena with me and build our relationship, and that’s OK because people who aren’t willing to get uncomfortable are likely not my people.

These conversations can be easier in the work environment, but too many workplaces don’t have a culture of healthy communication and persist with  ‘talking behind other people’s backs’ to process grievances. This ultimately leads to no action and strained work environments.

There are a lot of industries in which employees don’t operate within a team, and many people work alone and don’t have to check in with others regularly. For example, private practice therapists & consultants, nutritionists, massage therapists, etc. So without practice it can take courage to be in situations where hard conversations are more commonplace. But it’s not impossible to open up in our personal lives.  

I have clear communication in all my on-boarding at my business where I expect, honour and value difficult conversations. I have stated it in my agreement, “talk to people, not about people;” this helps remind the staff and myself how much I value that. People who aren’t willing to have those conversations ALWAYS end up creating drama and issues behind the scenes, which amplify into situations that were preventable.

I’ve been in management roles for more than 20 years, and drama has always occurred from a lack of willingness to have difficult conversations on either side of the equation.

Difficult conversations don’t always end in rainbows and unicorns, sadly. In the example I gave at the beginning of this piece, the friendship fell apart because the other person wasn’t willing to have the difficult conversation. I’ve made peace with it, and as sad as it was I’m grateful to know this now instead of investing years into a relationship that wouldn’t grow with me.

I’ve studied leadership, listening and communication for two decades and I still fumble through it. I came across a beautiful podcast episode about difficult conversations and how to have them:  check out Tim Ferris podcast episode #532 HERE. 

This is one of the most important listens I’ve had in my years of learning on this topic.

However, when I get back to the question of “when is a good time to have a difficult conversation?”, I recommend the sooner, the better. Some people suggest within 24 hours. I sometimes need more time than that to regroup. However, If I take too much time, I make the ‘incident’ into a much bigger event and it gets harder to have a conversation. It’s easiest to do when we’re not triggered and overwhelmed, but if we have too much time our minds will try to keep ourselves safe by convincing us why we shouldn’t have the conversation or why the other is a horrible person.

I’ve fumbled through many difficult conversations, but I’d rather do that in person than spend months or years in my mind facilitating conversations that never happen.

May we all fumble through the discomfort of conversations to make our time on this planet one of growth instead of rumination, avoidance and us versus them. 

xo, Noelle