Four Steps to Prepare for a Difficult Conversation

I was naively under the impression that no one likes to deliver bad news. Or difficult news. Or news you think the person might take badly. Or any message that will put someone in an awkward or embarrassing position. That was until I met my husband.

Some of you out there are like him. You embrace conflict. You feel the truth is always best and shouldn’t be hidden, minimized or sugar-coated. Some carry a personal calling—with the best of intentions!—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. Here is a game-changing freebee at the top of this article for you: If the topic will be someone’s lackluster performance, it is only about that. It isn’t—nor should we allow it to become—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. Based on fact. Real events. Words and actions that were heard and seen.

Here are four things I try to keep squarely in view.

First, those objective (indisputable?) facts are not weapons. Instead of “firing” them at the person, picture “laying” them on an invisible table between you. (Real tables between us are usually hindrances for these conversations, by the way.) 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 (video). Sharing shorter snapshots (pictures) brings the moment or behavior in question into focus quickly, saving agonizing moments (replays). This is mercy—making the point while sparing the detail.

This leads to the second—be extremely diligent to use a kind tone and slower speech, not just at the beginning of the conversation, but throughout (thus, the diligence). Do all you can to maintain these even if the person reacts … well, in any one of several “more animated” ways.

And what if they get angry? “What, at me? I’m just trying to help! Anyone else would have half the compassion I am showing right now!” First, if you are thinking this, you might not be in the best mindset to have this conversation. Second, 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 some (or all) of embarrassed, ashamed, regretful, disappointed and humbled by this conversation. And all laid bare before your eyes.

Right … Woah.

So, 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—or you wouldn’t be having this conversation.

Third—while we never want to overplay the sympathy card (“I know how you feel.”)—some empathy goes a long way (“You must have been surprised that he took what you said that way.”). 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. My husband says, “You can’t un-ring that bell!” and people have a way of noticing things once they have been brought to their attention, initially believing or not.

Finally—this is my own, as a recovering “judge”—I mentally picture dropping all the stones I might have in my fists to the ground far from my eager and possibly adrenaline-filled fingers. 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,” similar to that of our medical colleagues? No matter. We each can decide to lead that way, oath or not.

I hope that whatever difficult conversations you may be in the middle of, or that are on your doorstep today, you are committed to building a foundation of referent power and trust with those you lead. In the current climate more than ever, believing “I am for you” will go a long way to help someone let down their defenses to hear your concern.



  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.”