• Ariana Friedlander

4 Steps to prepare for your next difficult conversation

"How do you typically prepare for difficult conversations like this?" I asked my coaching client as he was realizing that he needed to have a direct conversation with his employee about a troublesome situation.

"I usually play it out in my head." He responded.

"And how has that worked out for you in the past?"

"Not great. It usually doesn't go as I had anticipated." He admitted.

I took deep breath and responded, "Well, you're not alone. Most people plan conversations that way. You play it out in your mind, anticipating what you'll say and how the other person will react. Usually, those types of 'movies of the mind' get us fired up. We expect the worst and lose sight of what we're really striving to accomplish."

"Yeah, I can see that." He said thoughtfully.

We were at the end of our coaching session together and he had another meeting to get ready for.

"This is one of those times that journaling can be really powerful. I can share some reflection questions with you, so you may prepare for this conversation by writing about it in your journal. How does that sit with you?"

"That would be great, thanks!"

This is a conversation I've had with a number of clients over the years. Sometimes we are able to prepare for a difficult conversation in a coaching session.


Inevitably, learning to use their journal and write as a form of preparation for difficult conversations is a worthwhile skill they can turn to again and again in their own time. What's more, this skill is helpful both personally and professionally.

Benjamin Franklin once said, "By failing to prepare, you are preparing to fail."

Preparing by playing out conversations in your head, anticipating how it'll go and mounting your argument to win, is inadequate. This is largely because such a technique for preparing is shortsighted. By writing out your thoughts, feelings, ideas, needs, expectations, observations and such you are able to get a broader more comprehensive perspective. You are able to separate fact from fiction. And you can keep the conversation focused on what matters most.

Perhaps you need to prepare for a difficult conversation. Here are some tips for using your journal to "PREPare."

  1. Process - What’s the situation that you need to address and with whom?

  2. Reflect - What has happened leading up to this point and what's your role been in this situation? What's the ideal outcome here?

  3. Examine - what assumptions are you making? What’s the story you’ve been telling yourself about the situation/the people involved? What's the point you're trying to make (I ask myself this question in particular frequently in my journal)?

  4. Plan - how are you going to approach this conversation so you (and others involved) are prepared for a constructive dialogue? What will you do to build trust? What if you approach the conversation open to being influenced by the other person's point of view?

Turning to the pages of your journal (or just writing in general) is an incredibly effective technique to prepare for difficult conversations that will save you time and energy in the long run.

The next time I met with my client I asked him, "So how'd your conversation go?"

He replied with excitement, "Better than I ever imagined possible."

What's more, the next time he had to prepare for a difficult conversation he said, "I'm actually looking forward to this conversation, Ariana. I never would have thought that before."

And that was the extent of our conversation about preparing for the next difficult conversation.


Once you cultivate the habit of taking to the pages of your journal to prepare for difficult conversations, you have the ability to self-advise anytime, anywhere to great effect.


Perhaps I'm working myself out of a job by teaching these skills. But that's ok, there's always more opportunities for growth - that is both the blessing and the curse of our shared humanity.

Want to connect with others, deepen your journaling practice and develop skills for self-advising? Join us for the next Journal Jam on February 23rd.

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