How to Prepare for a Difficult Conversation

Exhausted pensive employeeSome people in the world embrace conflict. They feel the truth is always best and shouldn’t be hidden, minimized or sugar-coated. Some carry a personal calling to hold people accountable for their actions, especially if they were less than acceptable and far from stellar. Their intent is to help us rise to our true potential. Or that is the idea.

The truth is most of us do struggle with the preparation and effective follow-through for what we believe will be a difficult conversation. If the topic will be someone’s lackluster performance, it is only about that. It isn’t about their personality, likeability or value as a human being. It is because we value them, in fact, that we would leverage the referent power and trust we have built with them to schedule a meeting and share our concerns.

How To Prepare For Difficult Conversations

Objective Facts Are Not Weapons

Instead of firing facts at the person, picture laying them on an invisible table between you. Lay them one by one. If there are several, carefully choose the order, trusting that only the first one or two will need referencing to get you both on the same page.

Lay them carefully, showing pictures, not videos. It puts people on the defensive to replay the scene in detail. Sharing shorter snapshots brings the moment or behavior in question into focus quickly, saving agonizing moments. This is mercy, making the point while sparing the detail.

Use a Kind Tone and Slow Speech

Be diligent to use a kind tone and slower speech, not just at the beginning of the conversation, but throughout. Do all you can to maintain this regardless of the person’s response.

What To Do If They Get Angry

Remember, in most cases, the anger isn’t really aimed at you, it’s a boomerang, circling past you and headed with laser-like accuracy back at them. Don’t miss that they are likely embarrassed, ashamed, regretful, disappointed and/or humbled by this conversation. And all laid bare before your eyes.

Give them a way out. Step on their toes without scuffing their shoes. Correct while keeping them whole. What do they think they could do about this? How do they think you can be supportive? Let these things be up to them, assuring them you believe in them and that better moments are ahead.

Use Empathy

A foundation of trust cultivates mutual respect and assures them, “I am for you.”

What if they deny or can’t see what you are trying to show them? Then let it be. Let the information you have shared sink in over the next few days.

Let Go Of Anger

Mentally picture dropping all the stones you might have in your fists to the ground. I can point to the scars and remember bruises that resulted from stones cast in my direction that found their mark. Can you?

Maybe there should be a managerial oath to do no harm.



  1. Who is it that you must have a difficult conversation with, in the next week or so? Do they know that you are for them? Are you? If not, why not?
  2. Review a recent “difficult conversation”—not for the purpose of beating yourself up over what didn’t go well!—but for the purpose of identifying one of the four steps above you could have used—and will use before “next time.”