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June 7, 2021

The Courage to Deliver Difficult Messages


Delivering difficult messages is at the very core of dealing with the tough situations many leaders face.

I was working with a leader who was preparing to make some significant changes in his organization’s structure, including people changes. As we talked more, and his eyes welled up with tears, I realized how tough these decisions were for him. In the end, it was the right thing to do—his customers’ needs had changed; the market had changed, and his organization wasn’t set up for success. 

Through our conversation, he was realizing how difficult this announcement was going to be. In many ways, this was a leadership litmus test—whether he had the courage to not just make a tough decision, but to communicate it with empathy, respect, and sensitivity. 

The Upsides to Delivering Difficult Messages with Respectful Authenticity 

We talked about how he could be respectfully authentic about his feelings while still providing the leadership needed to paint a picture of a new future and deliver some difficult messages: 

  • Clarity would be critical (what is happening and why).
  • Courage is needed to be direct and straightforward.
  • Compassion and care are vital in communicating how difficult but necessary the changes are.
  • Creating a conversation about current and future plans. 

In the end, the changes were accepted as well as could be expected. As important, his team got an even better sense of this leader who showed great compassion and courage. 

In many ways, his ability to communicate effectively was integral to leading and managing change. 

He’s someone you’d want to work for in a heartbeat. And his advanced communications skills make the difference. 

What difficult conversation do you need to have, and how do you do it with compassion and care?

—David Grossman

Plan your communication—whether it's to a colleague, your team or company-wide—in as little as 5 minutes. Click the image below to download your copy of this free tool—Take 5™ Planning Template.

Click to download the free communication planning template - The Grossman Group

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