A Step-by-Step Guide to Navigating Difficult Conversations

Here’s what it looks like when you turn something you’ve been dreading into something positive.


Anticipating a difficult conversation—focused, for example, on poor job performance, or a team member who isn’t sufficiently collaborative—is a surefire way to lose some sleep.

About two-thirds of people worry about the reaction of the person on the other side of the table or video call, according to a recent FranklinCovey study. Indeed, fear of eliciting a negative emotion is the No. 1 reason leaders and managers avoid having difficult conversations.

But this fear does more than generate sleepless nights. My experience tells me it’s part of why these tough talks so often go poorly.

In fact, my career has been defined by approaching such conversations with what can only be described as the opposite of avoidance. In the 18 years I was FranklinCovey’s chief people officer, I had thousands of difficult conversations. Something that even experienced, articulate leaders postpone and procrastinate over was a part of my daily life for nearly two decades. In my countless exchanges, I learned that difficult conversations aren’t fun, but they’re unavoidable—and there is a clear set of best practices to achieve a positive outcome.

Best Practice #1: Prepare

The strategy that will allow you and your team to break out of established patterns and habits is to turn tension into progress. What does it actually look like to turn something you’re dreading into something productive?

The first step is preparation. The one thing you know for sure is that just by asking to talk, you will raise the antenna of any employee. The minute you signal you want to have the kind of conversation that represents a departure from the daily norm, you know you likely will put people on the defensive.

It’s this element that keeps so many leaders from even starting. Emotions can be complex, but the emotions you’re likely to elicit by asking to have a talk are often quite simple: It’s fight or flight. It’s a defensive crouch that makes it difficult, sometimes impossible, to share any information.

In order to break through that armor, you need to know what you’re going to say and how you’re going to say it. You need to anticipate the set of potential responses you’ll get from a team member who, even if you do everything right, might very well feel cornered and perhaps even verbally strike back.

What you say to a certain employee is going to be entirely dependent on the situation you find yourself in. You can have a dozen different employees with the same performance issue, but how you approach them and how the conversations flow are entirely dependent on the context.

Best Practice #2: Declare Your Intent

What doesn’t change is what you do next: Declare your intent. Right up front, you need to tell the person you’ve asked to speak with the truth—that it’s going to be a difficult conversation. But more importantly, you need to tell them why it’s necessary that you’re having it: You want them to be able to do their absolute best, you think they’re capable of it, and you’ve noticed habits or decisions keeping them from reaching that potential.

Leading with this positive intent is key in communicating one of the main principles of difficult conversations: Courage and consideration. Courage comes in the form of simply having the conversation. Consideration is in your approach. By declaring positive intent, you show how the other person can benefit from having the conversation and establish it with a clear and collaborative tone from the start.

This undercuts one of the central anxieties of those forced to prompt the difficult conversations. There’s often a misguided sense among leaders that the talks are going to hurt, but all that can be done is minimize the pain. This helps explain why those conversations are so often avoided. Pain reduction isn’t the best-case scenario—progress is. The person prompting the conversation can realize this only by focusing on balancing the needs of both participants.

To be sure, even the best declaration of positive intent won’t head off all negative outcomes. People are emotional. The conversation wouldn’t be happening if there wasn’t something wrong, and if that something wasn’t important enough to call attention to it. For that reason, expect a certain amount of defensiveness, possibly even anger. What’s important is what you do next.

Best Practice #3: Establish that You Have Empathy

Make sure there’s a box of tissues in the room. If the conversation gets too emotional, suggest a pause. If true, let the person know that you’ve been through something similar. Do not say you know exactly how they feel; again, the context of every difficult conversation is going to differ. But at least establish that you have empathy for them. And, as a way of further promoting the idea of positive intent, let them know the good outcomes that you hope for.

Remind them that this is a lot to absorb. Take the onus off of them to react in the moment, because their in-the-moment reactions are likely not going to be the best version of themselves. Keep the conversation as short as possible.

Best Practice #4: Follow Up

Always follow up soon afterward. I’ve encountered countless scenarios where someone had a difficult conversation and nothing positive transpired as a result. It’s the worst of both worlds: the pain of prompting the conversation without the progress. To try to prevent that from happening, follow up quickly with an e-mail and provide a summary of what you talked about. Always ask them to review it and let you know if there was anything you’ve left out or if they had any questions.

There’s power in putting it down in writing. It may be that your team member didn’t really absorb what you were saying in the moment because they were feeling too many powerful emotions. A little distance, and a clear-headed recitation of the conversation, can work wonders for producing the kind of clarity you’ll need to make progress.

Courage and Consideration

Courage and consideration are the twin pillars of difficult conversations. They represent your mindset and what you hope to project to the person who not only needs your attention, but also needs your help improving. Everything flows from those two ideas, because it takes courage to move past the tension, and it takes consideration to turn it into progress.

To learn more, attend Davis’ webinar on Training Magazine Network, “Navigating Difficult Conversions: Turning Tension Into Progress,” on March 7, 2024, at 12 p.m. Pacific/3 p.m. Eastern or click here.