Pro Tips for Courageous Conversations

You know the feeling — anxiety or dread about a conversation you know you should have. What should I say? How will the other person react? What if…? You wish you didn’t have to have the conversation and that the problem will just go away, but avoidance usually makes it worse.

Leaders and change agents face these conversations all the time: managing staff performance, struggles with the board, negotiations with funders and clients, or conversations about power and privilege can all trigger these feelings.

The notion of Courageous Conversations invites us to a paradigm shift: rather than necessary evils, these conversations are critical opportunities to advance our work and mission.

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The Courageous Conversations Toolkit is one of the most powerful and popular tools in our library, having helped hundreds of leaders and change agents meet and transform interpersonal challenges to build stronger teams with deeper trust and greater effectiveness.

At our most recent Community of Practice gathering for Art of Transformational Consulting alumni, Robert Gass facilitated a refresher on Courageous Conversations. He asked the consultants present what they had learned about how to make Courageous Conversations successful.

Their answers are great additions to the Courageous Conversations toolkit.

View the other person in their wholeness, from a place of love, with the belief that they can handle what you’re going to say.

Ask for permission to have the conversation before starting it. Don’t ambush the other person — give them the chance you’ve had to mentally prepare for the conversation.

Always do a POP before any Courageous Conversation. That’s the Fabulous POP Model, a simple and powerful practice of articulating in advance the Purpose, desired Outcomes, and Process for any significant action.

Start with open questions, and really listen to the answers. Never assume you know someone else’s motives, or what they feel. Beware of confusing “my truth” with “the truth.”

Courageous Conversations has an “s” for a reason. Sometimes multiple short Courageous Conversations work better by providing breaks from pressure and stress and offering everyone opportunities for self-reflection.

Consciously open my shoulders and my heart. These are useful somatic reminders of some core tenets of Courageous Conversations: come from a place of purpose and authentic power, and also from a place of love and compassion.

Deal with the delusional perfectionist in me who imagines that somehow if I do it just right it will all go perfectly, and the other person will actually thank me. Let go of the behavioral response that you want or expect from the other person, and “just take care of my side of the street.”

Redefine success. Sometimes just the release and courage to have the conversation — to break the silence and name what needs naming — makes all the difference, no matter how the conversation goes.

We hope the Courageous Conversations Toolkit and these pro tips will inspire you to think of difficult conversations as Courageous Conversations, and seize these opportunities to develop authentic connections and strengthen your leadership. Needless to say, cultivating the art of Courageous Conversations can be extremely beneficial to your personal life as well!

You can probably think of a Courageous Conversation waiting to be had right now… what are you waiting for?