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Writer's pictureElliott the Wiener

Mastering the Art of Courageous Conversations: A Guide for Leadership Success


A red wiener dog wearing a jean jacket
Wiener Dog Leadership

Dear Elliott,

How do I have courageous conversations with my team without creating defensiveness or damaging relationships?


-The Courageous Leader in Training

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Dear Reader,

Courageous conversations are a powerful tool for leaders. They can resolve conflict, inspire change, and build deeper trust within teams. But you're right—the challenge is navigating these talks without triggering defensiveness or damaging relationships.


Here are some key steps you can follow to make sure these conversations are effective and constructive:

  1. Prepare with Intention: Before diving into the conversation, ask yourself: What is my intention? Are you seeking to resolve an issue, share feedback, or clarify expectations? Being clear on your purpose will help keep the conversation focused and productive.

  2. Lead with Empathy: Remember, the person on the other side of the conversation is likely feeling vulnerable too. Approach them with empathy and understanding. You might start by acknowledging their contributions or feelings before introducing the difficult topic. This sets a tone of respect and care, rather than confrontation.

  3. Use “I” Statements: Rather than pointing fingers or blaming, frame your concerns from your own perspective. For example, instead of saying, "You're not doing this correctly," try, "I've noticed that I'm having trouble seeing progress in this area, and I want to work together to figure out why." This approach reduces defensiveness and opens the door to collaboration.

  4. Pause and Listen: In the heat of tough conversations, it's easy to fall into the trap of talking at someone rather than with them. Pausing to listen can be one of the most courageous moves you make. Give the other person space to share their thoughts, perspectives, and emotions. Listening shows that you value their input and are willing to understand their side.

  5. Own Your Vulnerability: Being open about your own vulnerabilities can encourage others to do the same. You might share how difficult it was to bring up the issue, but that you're doing it because you care about the success of the team and the individual. This honesty can foster a more open and trusting environment.

  6. Be Solution-Oriented: After discussing the issue, focus on finding a way forward. Ask the person what they need from you to improve the situation and offer your support. This reinforces that the conversation isn’t about assigning blame but about collaborating for a better outcome.

  7. Follow Up: Courageous conversations shouldn’t end when the discussion does. Set a time to follow up, see how things are progressing, and ask if further support or clarity is needed. This shows your commitment to the relationship and the resolution of the issue.


Remember, courageous conversations are about growth—for you and for those you lead. While they can be uncomfortable, they’re a sign that you care enough to address important issues head-on. Keep practicing, and with time, these conversations will become not only easier but also more meaningful.


With courage and empathy,


Elliott, Chief Morale Officer, @Break the Norm Leadership

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