How to prepare for a difficult conversation

I was recently dreading a conversation I needed to have. It was the kind of thing that had to be in person, and I even scheduled it on my calendar. Because I was dreading it, I prepared a lot for it. And that was surprising, because although I typically do a lot of overthinking about things, I don’t necessarily do a lot of preparing.

The conversation went better than I thought, and the whole situation made me realize the difference between just replaying different scenarios in your head and actually concretely taking steps to get ready for something. So, with that positive experience fresh in my mind, here is what I learned …

First of all, pray for the situation.

Pray when you first realize the discussion needs to happen, and then pray moments before, and then pray during the discussion itself. If you take nothing else from this article, this is the most important.

A couple of saints you could ask for help include two doctors of the church: St. John Chrystostem and St. Teresa of Avila.

“Chrysostom” was the name given to this 4th-century archbishop. It means “golden- mouthed” because St. John gave beautiful and practical homilies that won many hearts for Christ. Ask for his help to make you eloquent in your conversation.

St. Teresa of Avila had a talent for being able to connect with people, whether they were rich or poor, men or women, religious or lay person. Ask her for a good dose of relatability and practicality to enhance you communication skills.  

Secondly, do your research.

This might mean looking more up on the topic you need to address, or it might mean learning more about where the other person is coming from even before you tackle the difficult conversation by asking questions.

In my case, I had a couple of pre-conversations that helped me understand much more clearly what was going on in the situation than I had previously. That left me in a much more open (and less defensive) place when the day came and it was time to talk. 

Finally, be ready to listen.

You may know what you want to say, but if you don’t actually listen to where the other person is coming from, you risk misunderstanding what is going on. What you want to communicate will probably still be valid and helpful if you are truly listening, but how you say it and what you emphasize might change based on what you hear.

I have found that the more you ask for grace in prayer, the more grace you get (or at least, the more grace you notice). So, I asked for lots of grace before and during the conversation. Also, before the conversation, I asked a few more questions about the situation and suddenly had a bunch of new, helpful information that allowed my thoughts to coalesce better on the subject. And in the thick of the conversation, when I wanted to just irritatedly say “you’re wrong in this way, and now let me explain how you should move forward,” I stifled that instinct. I waited. I took a breath. I asked another question and listened. And, that little bit of a breather helped me communicate my points more calmly and collectedly a few minutes later when the time was right. 

St. John Chrysostem and St. Teresa of Avila, pray for us!