You know what I am talking about. You must deliver a message to a group or individual that they aren’t going to love. This isn’t likely one of your favorite parts of being a leader, but it comes with the territory. Messages about organizational change, process change, individual feedback, or something surprising in any way. This is part of your job, and not one of the good parts. But you can do it with greater confidence and grace, and get better results too. Here are five ideas and approaches to help in those inevitable times when the difficult message is yours to deliver.

Think Environment and Timing 

Where and when a tough conversation takes place is important. You likely wouldn’t dream of having a tough conversation in a crowded restaurant or the company cafeteria, but the point is more subtle than this. Where will people feel a level of comfort? Where can they have the chance to hear the message and not have to interact with other people immediately afterwards? Think about the timing, too. Some leaders (this has been me at times) put off the difficult conversation. And the longer we put it off, the harder the messaging becomes. Delivering difficult messages should come sooner rather than later. Find or create a situation where you are ready to send it and the recipients are ready to receive it.

Be Prepared - But Not Too Prepared

Because this message will be tough, we want to have all our data, all our facts, and everything in line. We might even decide to write a script. We think if we get the words just right, the conversation will magically go well. (Hint: There is no guarantee of that.) If you are completely “prepared,” you focus on “getting your message across.” This means you are less likely to listen, adjust, and shift based on the responses of your audience. Rather than focusing on planning every detail and crafting your words perfectly, focus on helping others clearly understand the message. Prepare so you can be clear, but not to overpower people with your preparation.

Hold Your Assumptions Loosely

“Difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations, and values.”

~ Douglas Stone, Difficult Conversations: How to Discuss What Matters Most 

As you think about delivering difficult messages, you are necessarily thinking about it from your perspective and applying your assumptions. While you can think about what you know about your audience and anticipate their reaction or concerns, hold on to that loosely. Be ready to shift and adjust based on how the conversation goes. Here’s an extreme example: Have you ever delivered what you thought would be something people didn’t want to hear or resist, and they actually welcomed it?

Think Conversation

By letting go of our preparation and assumptions, we give ourselves space to make delivering difficult messages less about us and more about them. Which opens the chance for a conversation, rather than putting pressure on us to deliver perfect communication. Remember, you can’t control the other person’s response – as much as you might want to. What you can do is bring a clear message and allow a conversation to take place. Conversation helps them see the message clearly, and perhaps even in a new way. As you explore the topic together, the chance for new understanding and awareness (for both of you) grows.

Ask More, Assert Less

If we want a conversation, especially as the leader, we must talk less - and replace our words with questions. You may come into the situation thinking “I understand.” But you need to shift your thinking to “Help me understand.” Shifting to that mindset allows you to ask more questions. Asking more questions allows the other person to teach you something, which helps them feel heard. Ultimately, the message might be disappointing, hurtful, or scary to the other person. But a conversation helps them feel more like a participant and less like a recipient. And participants are more likely to reach a sense of peace with the tough message sooner. Even if they don’t love it. Plus, asking questions in a curious, gracious, and empathetic spirit greatly improves the nature – and likely the outcome – of the exchange. Tough messages can actually improve our relationships with those involved, when delivered thoughtfully.


These five ideas won’t make delivering difficult messages your new hobby or favorite part of your job. But they will give you greater confidence, reduce your stress, and make delivering those messages easier with better results.

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About the Author

Kevin has spent 30 years helping organizations and leaders from over 40 countries become more effective. Inc.com has twice named him in the top 100 Leadership and Management Experts in the World. His books include Remarkable Leadership, From Bud to Boss, The Long-Distance Leader, The Long-Distance Teammate, and The Long-Distance Team.

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