10/21/2025 – 4 Ways to Build Courage for Difficult Conversations

Some people go through much of their lives avoiding hard conversations.

Instead of having uncomfortable talks, they find it easier to be angry on the inside.  

Instead of moving forward in life, you find yourself in a cycle where:

  • Coworkers keep dumping work on you
  • You keep fixing other peoples’ work instead of giving them the feedback they need
  • Neighbors’ annoying behaviors aren’t resolved
  • Friendships end when you don’t speak up for your boundaries

You know deep down that you could probably resolve some of these things with one or two hard, uncomfortable conversations…

But how do you start? 

Especially because you know it’s freeing to rip that bandaid off and deal with things much sooner.

These are the practices that consistently help people overcome that avoidance:

1. Self Reflect

Do some self-reflection on what you are struggling with the most:

  • Worried about the other person’s reactions?
  • Worried about not knowing what to say?
  • Worried you don’t know how to handle their potential reactions?

Write out every thought you’re having and evaluate how likely they are to happen.  

If they are likely, create a plan to address it or practice it.

Take your thoughts and start challenging yourself directly – avoidance often starts and ends with mindset.

2. Practice Low Stakes

Find a low stakes conversation that you could practice on.  It doesn’t have to be something you’re actively dealing with.  It might be as simple as asking for a discount on your meal at a restaurant or asking for a free meal at McDonald’s.  

It’s not about getting a specific result, it’s getting comfortable hearing “No”.  

A little exposure therapy and a little practice saying what you want to say.

3. Practice with a friend

Find a low stakes conversation that is something you’re dealing with and practice with a friend.  Have them start by taking it easy on you.

Write out a script of what you want to say and see what lands.   

4. Read Books/Watch Movies and TV shows with hard conversations

Read books or watch movies/tv shows of difficult conversations and situations.  Pause the scene or cover up part of the conversation and practice how you would respond or what you might say.  

Bonus points if it’s a scene that is particularly emotional for you.  

It’s an extremely underrated way to simulate real life scenarios without paying for virtual reality. 

This won’t be an easy fix.

But, “slow motion is better than no motion”.

As a leader, learning to step into hard conversations is what helps you build trusting relationships.

As a person, learning to step into hard conversations is what helps you live more authentically.

What else has helped you get better at starting difficult conversations in the first place?

PS – This is part of the course I’m running next month, TRUST – all about leading through tough conversations. I’d love to have you in the first group. Details are here [https://www.myleadershippotential.com/trust]

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