08/13/2025 – 5 realities about difficult conversations

Read on my website here (2-minute read)

I was inspired by a colleague’s recent post for today’s newsletter.

I wanted to share 5 realities about hard conversations that we need to acknowledge.  Because even though lots of people talk about how to get better at them, there are some things that will always be present.  

And knowing them isn’t about conquering them, it’s about helping you keep realistic expectations and knowing how to work around them.

  1. Hard conversations will always be hard

The reality is that difficult conversations will always be difficult. The nervousness might decrease over time, but the higher the stakes – the more you’ll still feel that anxiety.  

Preparation and experience will help you be more prepared, but the feelings of anxiety and nervousness?  

That’s normal.

So lean into it and recognize the importance of self-care, coping skills, and taking care of yourself.

  1. Sometimes, the conversation will be just about ground rules

The more tension in the relationship and the higher the stakes, the higher the odds that your first conversation may just be about setting ground rules, and calming the other person down.

You may not even get to the main topic.  

Don’t stress – getting on the same page about ground rules, communication preferences, and styles isn’t just an intellectual exercise – it can build rapport and trust.

  1. It’s possible to do everything right and still lose

This is a quote I love from Star Trek.  (though, I’ve never watched the show, just seen this clip)

It’s possible to prepare the right way, say all the right things, and still come up empty or the conversation still not be productive.

Don’t take it as if you did anything wrong.  

Sometimes, it’s just not in the cards, no matter what anybody says.

  1. It’s ok to be angry at the other person

Occasionally, I’ll run into people who feel guilty about being angry at the other person.  They don’t always say it of course, but it still comes out.

They’ll stop themselves from saying what they really want to say when they’re describing the situation. 

They’ll struggle to use “nice” language to describe the other person.

But the truth is, it’s ok to be upset at them.  

It’s ok to think they’re a bad person, or immature.  Your feelings are valid.  

And it’s ok to vent to someone you trust about it and say what you really want to say.  Sometimes it’s just nice to release the valve

  1. Scripts can only take you so far

Many difficult conversations and communications courses (including mine) give you scripts or ways to say things.

And they work (or else we wouldn’t suggest them).  

But they only go so far.  

At the end of the day, you have to find a way to turn them into your own voice.   It’s very similar to learning an instrument.

When you first start, you learn the basics and how to play other songs.  

But as you progress, the only way to make it your own is to start entering your own voice into it.  

The more you make it your own, the more authenticity and rapport you can build while making it your own.  

That’s when you truly can feel authentic in difficult conversations.

What are your thoughts?  Anything else that we don’t talk enough about in hard conversations?

Cheers,

Chris

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PS – Whenever you’re ready, I have 3 ways to help you:

  1. Let’s connect >>  If you’re struggling with difficult conversations and relationships, let’s find time to connect.  I’d love to see how I might be able to support you.
  2. Team Reset Program (TRP): A 6-week guided reset for leadership teams that need to rebuild trust, address what’s not being said, and start operating like a real team again.

TRUST: Learning to Say the Hard Thing:  A 5-session small-group cohort for leaders who want to navigate high-stakes conversations with clarity, confidence, and courage.

Interested in learning more about either?  Reply to this email with “TRP” or “TRUST” and I’ll send you the overview.

  1. Podcast: The Art and Science of Difficult Conversations. >> If you’re interested in more ways to manage difficult conversations, I also have a podcast, available wherever you get your podcasts and on YouTube

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