How to Have Difficult Conversations

When you need to deal with an awkward topic, it can be tempting to run from it. Screaming. But with Get-It-Done Guy's approach, you can master the difficult conversation and make your life a lot easier. 

Stever Robbins
5-minute read
Episode #366

How to Have Difficult ConversationsEuropa unfortunately mixed up several purchase orders for Bernice's plant stores, Green Growing Things I and II. Deliveries were made to the wrong addresses, and by the time it was all sorted out, new purchases had been made, inventory was duplicated, and everything was a mess. The cost overrun is high enough that Bernice wants Europa to pick up half the bill. Every time she sees Europa, she gets a sinking feeling in the pit of her stomach because Europa is her friend, and she hates the idea of bringing up the topic. So instead, she comes into my office and tells me, corners Melvin in the stockroom and tells him, discusses it with her friends outside work, and pretty much hashes over the situation with everyone except Europa.

Sound familiar? As far as I can tell, the number one strategy people have for having difficult conversations with each other is avoiding the conversation altogether. What happens when you avoid having a difficult conversation? As far as I can tell, it almost always makes things even more difficult. For example, my friend, Ashley, was in a long-term relationship that came to an abrupt end when the significant other, who we'll call "Evil Shmoopie" for short, announced out of the blue that they were breaking up. What multiplied the trauma for poor Ashley is that Evil Shmoopie had said during multiple recent relationship discussions, that the relationship was fine and that long-term was the way to go. So not only did Ashley not see this coming, but Evil Shmoopie also turbo-charged the missile before firing it. When you're old and wise like me, you've been on both sides of that particular missile (wait... how many sides does a missile have?).>

Their Story Is Probably Different from Yours

I don't know Evil Shmoopie, but I'm willing to bet that this wasn't a horrible, evil deception intended to stab Ashley in the heart and create a lifelong distrust of love and rejection of intimacy. I'll bet Evil Shmoopie was actually thinking something like this: "I don't want to be together with Ashley romantically, but I still care deeply. I really, really don't want to do anything that would be hurtful to such a wonderful person. Admitting I don't want to be together any more would be hurtful, so instead, I'll lie and say everything is fine." Was Evil Shmoopie deceptive? Yes. But only because they didn't know how to have a difficult conversation with Ash. Avoiding the difficult conversation was intended to spare Ashley's feelings, but instead, it made the ultimate breakup far more painful. (And by the way, if Evil Shmoopie is listening, I expect you to pick up the bill for Ashley's therapy, just as Bernice expects Europa to help cover her mistake.)

The Right Approach Makes Difficult Conversations Easy

The book Difficult Conversations by Douglas Stone, Bruce Patton, and Sheila Heen lays out a simple, but powerful framework for approaching difficult conversations. Each conversation, you see, is really three conversations. It's a conversation about facts, a conversation about feelings, and a conversation about identity. When you're going into a difficult conversation, get those three conversations clear in your mind, and use them to help resolve things with the other person. Everyone has their own story. The problem isn’t your story or their story. The problem is the difference between the stories. That difference can arise in any of the three conversations.

Differences Can Be About Facts

The first conversation is about the objective facts of the situation. Without a mutual understanding of facts, the rest of the conversation will fall apart. Want proof? Look to politics.


About the Author

Stever Robbins

Stever Robbins was the host of the podcast Get-it-Done Guy from 2007 to 2019. He is a graduate of W. Edward Deming’s Total Quality Management training program and a Certified Master Trainer Elite of NLP. He holds an MBA from the Harvard Business School and a BS in Computer Sciences from MIT.