01/08/2025 – 🔍 5 Core Reasons Why Difficult Conversations are hard

Maybe you’re the kind of person that always wants to know WHY things are happening or WHY they’re going wrong.

So of course in hard conversations it’s frustrating when you freeze up or forget what you want to say or get thrown off by the other person’s behavior.  Especially if you’ve been working on this for awhile and you can’t seem to get over the hump. 

There are lots of fancy books out there (many of which I love) that can dive deep into what’s going with you – and potentially a therapist could help too. 

But let me help you cut through all of that – difficult conversations are difficult because of these 5 main reasons:

  1. We care about both the relationship AND the outcome.

Oftentimes, we struggle because we want to get a specific outcome from that conversation AND we want to preserve the relationship in some way – even in work settings.

Now, it doesn’t mean you want to be best friends with everyone you work with, but you want to maintain at least a cordial relationship or have them like you.  If you didn’t care at all about either, you’d either just say what was on your mind without caring about their feelings (you care about the outcome, but not the relationship) or you’d let them do whatever they want (you care about the relationship, but not the outcome).

  1. It’s hard for us to be vulnerable

The way I was raised was to never talk about feelings (except happy ones) or personal issues.  If you were raised that way, it’s hard to suddenly be put in a spot where you have to reveal your innermost thoughts, desires, concerns, fears, etc.

  1. It’s human nature

It’s also human nature and neuroscience that when we’re faced with a perceived threat, we resort to our base instincts – our fight, flight, or freeze response.  When faced with a hard situation, you either want to:

  • Fight (argue, yell)
  • Flight (run away, disengage) or, 
  • Totally freeze up  

It’s how we’re all wired.  In fact, it’s how the other person is reacting too.  The sooner you recognize that and come to terms with it, the more you’ll start noticing it in yourself and others.

  1. Our minds limit us

Ever walk on a hiking trail?  Ever notice how much easier it is to follow it then to create a new trail?  That’s how our brains work.  

From a young age, you believed something about conflicts or confrontation that made you avoid them.  

Now, it’s just a natural habit for you to approach them that way.  

Mastering difficult conversations doesn’t start with how to manipulate others – it starts with learning how to master ourselves and our own mindsets that hold us back.

  1. We don’t have a plan

Maybe you actually feel super comfortable with the idea of conflict, if so, that’s great.  

But you may still be getting stuck on the idea of how to actually facilitate and bring somebody else through the process.  

Working on our mindset is the beginning, but it’s not the end – we do also need to have a plan of how to facilitate and guide the conversation.

As you read through the 5 reasons, there may be only 1 thing here that resonates with you. 

You may identify with all of them.  

That’s ok, it’s not either/or.  Multiple things can be true at the same time.

The important thing is, does this help you get more clarity on where you’re getting stuck?

Reply back and let me know which of these describes you!

Cheers,

Chris

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

  1. Free Strategy Assessment >>  If you’re a nonprofit leader, take a free, 5-minute quiz to evaluate your nonprofit’s strategy implementation plan
  2. 1-hour Effective Performance Coaching Course >> If you’re a manager looking for strategies to be better at coaching your employees, take this free 1 hour course to boost up your coaching ability
  3. 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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