Are You a Leader Who’s Brave Enough to Start a Conversation That Matters?

Unfortunately, many people shy away from conversations that matter. In the current political and social climate, it might feel too overwhelming to even try! However, if you want to be an influential leader that inspires your community, these kinds of conversations cannot and should not be avoided. This isn’t talking, tweeting, or shouting, this is conversing, and it comes from a place of vulnerability.

This subject came up for me recently when I read, Margaret Wheatley’s poem, “Turning to One Another.” (To read the entire poem take a look at my last blog, Appreciating the Power of a Collaborative Community — Now more than ever!)

The second stanza of the poem stimulated some thought-provoking questions…


Be brave enough to start a conversation that matters. 

Talk to people you know.

Talk to people you don’t know.

Talk to people you never talk to.


Be intrigued by the differences you hear. 

Expect to be surprised.

Treasure curiosity more than certainty.


So here are the questions that come to mind…

  • Who can you have a brave conversation with — can you find someone you know, don’t know, or someone you would normally never talk to? 
  • What are the brave conversations you need to have? 
  • How can you have a brave conversation? 
  • How can you create a brave space, and listen, openly, to all the differences in the conversation?
  • How can you get to know people you don’t know very well, listen for differences and commonalities, and be curious about other people’s stories?

Before you consider those questions in the context of your own life, let me share with you something helpful. In Peter Block’s book, Community, he describes the difference between conversations and talking. An important distinction, conversations produce something while talking does not. 

Conversations produce…

  • Invitation
  • Possibility
  • Ownership
  • Dissent
  • Commitment
  • Gifts

These are the doors to transformation. This is where brave conversations can begin. 

I try to have brave conversations but then I find myself drifting into talking. I reflect and wonder what is holding me back. I recognize that I simply have more investment in not changing, in keeping that door to transformation closed. Rather than “treasuring curiosity” as in the poem, I treasure the security of not knowing. Rather than expect surprise, I fear surprise. What if I don’t like the surprise? 

In one poignant conversation recently, I opened with a brave conversation starter and clearly triggered the other person. I received a slew of negative feedback about me, what an unhappy surprise! However, I had to examine the feedback and own what was truly mine. Then I had to determine what needed to be discarded as unwarranted based on the other person’s rejection of my conversation starter. Accepting that there is truth even in the negativity is a door to transformation. Accepting that there are items to be disregarded because the person was simply lashing out is also an important door to transformation. Owning what I can and discarding what I cannot, should not, or sometimes will not own.

Think of brave conversations as the opening for something to happen. As Margaret Wheatley prompts us in her poem, talk to everyone and listen for what’s there. Then, follow Peter Block’s guidance and move into a conversation. And, then, see what is possible. I would love to hear from you about a brave conversation that results from reading this post! Please feel free to reach out to me.

Louise J Santiago, PhD
Executive Coach and Organizational Consultant

Where Leadership is Intentional Work

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