How to Start a Difficult Conversation with Your Direct Report | Step-by-Step Guide for Managers

What do you do when you need to have a tough conversation with someone on your team?

Maybe it's about poor performance, missed deadlines, or perhaps it's a behavior that's disrupting the entire team.

These conversations are never easy, but they're absolutely necessary if you're a manager. And the way you start these conversations can make all the difference between a positive outcome and a defensive, unproductive one.

Today, I'm going to show you how to start difficult conversations with your direct reports in a way that sets the right tone, and promotes understanding and leads to real improvement.

Hey everybody, and welcome back to the channel. I'm Doug Howard, and if you're new here, I help managers and leaders develop the skills to lead with confidence, handle tough situations, and build high performing teams. So if you're looking for practical tips and strategies to become a better leader, make sure to hit that subscribe button and turn on notifications so that you never miss an episode.

In today's video, we're focusing on one of the toughest parts of being a manager, and that's starting difficult conversations with a direct report. Most managers dread these conversations, and for good reason too, but if you approach these conversations the right way, they can be an opportunity for growth, learning, and a stronger working relationship.

I'm going to walk you through a step by step framework that's going to help you start these conversations with clarity, confidence, and compassion.

Common Mistakes Managers Make

Let's start by talking about where most managers go wrong when handling difficult conversations. Most managers make the mistake of either sugarcoating the issue or being overly direct without considering the impact they're having on the other person. They often make the mistake of trying to soften the blow with a compliment sandwich. That's where you're giving praise, then criticism, followed by more praise. Or they make the mistake of dancing around the real issue, hoping the other person is going to get the hint on their own. All of these mistakes usually happen because managers want to avoid conflict, or avoid hurting the other person's feelings.

Let's face it, nobody wants to be the bad guy, and they don't want to come across as being too harsh, or they don't want to damage the relationship with that person. So they end up being too vague, or they end up being overly cautious when they're having the conversation. The intention is good, so I'm not here to criticize you.

You want to keep the conversation light, you want to preserve morale for the other person, but the reality is that it often has the opposite effect on the other person. This is because when you beat around the bush, it creates confusion for the other person. The person leaves the conversation unclear about what needs to change or how they need to improve. They may feel like they're doing fine because of the compliments you gave them, or they might not fully understand the issue because it wasn't clearly stated to them. Regardless, any of these scenarios prevents them from taking meaningful action and learning from the feedback.

Now that you understand the context behind why most managers make these mistakes, let's take a look at the framework for how you should start a difficult conversation with your direct report.

Step 1 - Set the Tone and Be Honest

The first step is to set the right tone for the conversation. This means you need to be upfront and let them know that this isn't going to be an easy conversation. Transparency is key here.

You may want to start the conversation with something like this. Hey Jim, I have a difficult topic we need to discuss and I want to be up front. It's going to be a little uncomfortable. Saying something like this signals that you're not going to sugarcoat the situation and it prepares them emotionally for what's coming their way.

Here's why this works. Setting the tone early shows that you respect them enough to be direct and honest, and it eliminates the guesswork and establishes a clear, transparent environment from the beginning. You're not leaving them wondering where this conversation is going. Instead, it's clear and straightforward. They know where it's going.

Step 2 - Don't Beat Around the Bush

One of the biggest mistakes is trying to cushion the blow with compliments before and after the criticism. Like I said before, the compliments sandwich. This often dilutes the message and creates confusion. So instead of giving a compliments sandwich, get to the point quickly and avoid any unnecessary fluff.

For example, instead of starting with praise, say something like, Hey Jim, I want to have this conversation because I know you value transparency and I want to give that to you.

Now, just to make sure I'm clear here. I'm not saying to disregard their strengths or their positive characteristics. It's important to acknowledge their strengths, but make sure you don't bury the feedback between compliments.

Being straightforward helps the other person understand the seriousness of the issue without feeling misled. It also respects their ability to handle the truth, and it encourages a more mature and professional conversation from both of you.

Step 3 - Give the Person a Good Name

Next, explain why you're having the conversation in a way that affirms their strengths. You may say something like, Hey Jim, I know you take pride in your work, and that's why I want to discuss some areas for improvement. I believe in your potential and I want to support you in getting there.

Doing something like this frames the conversation positively and makes it clear that your intention is to help them grow. This technique is inspired by trial lawyer Jefferson Fisher, and it's known as giving a dog a good name. The concept behind giving a dog a good name is if you give your dog a good name, the dog is gonna be a good dog. But if you give your dog a bad name, it most likely is going to become a bad dog. Now, not to compare people to dogs, but it's just a good way to make that point.

What I mean by giving a dog a good name is, you're highlighting their strengths and you're reinforcing that this isn't about attacking them personally. Instead, you're giving them a positive reputation to live up to, and you're showing them that this conversation is about helping them reach their full potential, which is going to make the feedback feel more like guidance and less like criticism.

Step 4 - Separate the Person From the Behavior

Moving on to step four. When you get to the heart of the issue. Make sure to focus on specific behaviors, not the person's character. For example, instead of saying you need to improve your presentations, because that's personal, instead say, here are some opportunities to improve this presentation. You see the difference there?

The goal is to make it clear that you're addressing the behavior and that you're not criticizing them as a person. Here's why this is super important. By separating the person from the behavior, it helps prevent defensiveness and it makes it easier for them to accept the feedback because it's not a personal attack. Again, this shifts the conversation from judgment to improvement. It keeps the focus on what can be changed rather than focusing on personal shortcomings that maybe they don't have any ability to change, or maybe they don't want to change that.

Step 5 - Invite Collaboration

Finally, we want to invite them to collaborate on a solution. That means making this a two way conversation. So this might sound something like this. Hey Jim, let's work together on improving in these areas. I'd love to hear what your thoughts are on what might help you out.

Doing this not only empowers them to take ownership of the solution, but it also shows that you're invested in their success. By you inviting them into the problem solving process, you're demonstrating that this isn't a one sided critique. Instead, it's a two way partnership aimed at helping them grow and succeed.

When you're going through this framework, remember, set the tone early, avoid the compliment sandwich, focus on their strengths, separate the person from the behavior, and last but not least, invite collaboration. These steps will help you have more productive, honest, and effective conversations that lead to real change and growth.

But starting the conversation is just the beginning. To make sure your feedback is truly effective and that it's driving action in the other person, you'll need to know how to deliver that feedback properly. That's why I invite you to check out my next episode called How To Give Constructive Feedback Without The Stress. In that video, I'll share a detailed framework for delivering constructive feedback that's clear, actionable, and respectful. I'll see you in the next video.

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