Skip to main content



January 29, 2020

The Conversation You Are Avoiding May Be Your Learning Edge!

Categories:  Leadership | Coaching

“Be brave enough to start a conversation that matters.”

– Dau Voire

The conversation you are avoiding is your learning edge as a leader.

Some of our favorite work with clients is facilitating, witnessing, and supporting our clients to have courageous conversations (with their staff, their peers, and their managers).

We also enjoy facilitating these courageous conversations “real-time” for the leadership teams with whom we work. No, this isn’t the first place we start with our client teams, however, it is an important skill to have. ????

What are courageous conversations? Courageous conversations are conversations that really matter – saying what needs to be said – even though you do not know where the conversation may go. They address what "may" be holding you, your team or a project back. They require that you be bold enough to tell someone what’s on your mind, even if you aren’t sure, you are right because something is still bugging you. We emphasize “may” here because until you have the conversation you honestly don’t know; you don’t have the other person’s perspective yet. Then again you “may” really know, and have known for a LONG time, but haven’t had the courage to speak up and say something, and the situation has deteriorated along with the relationship, project or team performance.

As leaders, it’s important to build this muscle. We have seen so many situations, where a leader waited too long to have a courageous conversation, OR jumped in too soon before cooling down or preparing.

If you take the role of leader seriously, it means you care, your perspective matters, and having conversations with those around you matters. It also means being bold enough to make and take the time to do it now and not wait. And then it is being able to listen – to really listen to the other person’s perspective.

Why don’t we have courageous conversations? Often what holds us back from having a courageous conversation is fear – fear of hurting another’s feelings, fear of rejection (e.g. not looking good), fear of failure, or fear of not being good enough to deal with the emotions that can arise in courageous conversations.

What does it take to have a courageous conversation?

  1. Be courageous and let go of your fears. Or, as Dr. Susan Jeffers said: “Feel the fear and do it anyway.”
  2. Don’t be attached to the outcome. When we attach ourselves to an outcome, we can attach ourselves to ego and not allow the collaborative process to unfold.
  3. Speak your truth. Be open about your thoughts, fears, and feelings; not just saying what you think others want to hear.
  4. Learn to enjoy the discomfort. Though it can be uncomfortable, it is through dialogue that healing and change can take place.
  5. Be curious. Ask questions to learn as much as you can about the other person’s perspective. Listen for what is not being said.
  6. Trust the conversation will create opportunities and possibilities and mutual understanding.

Benefits of having a courageous conversation:

  1. Gain wisdom from a larger perspective
  2. See things from another’s perspective
  3. Learn something new about yourself or another
  4. Create trust in the relationship
  5. Provide a safe environment for co-creation and collaboration

Tips on conducting a courageous conversation:

  1. Prepare for the conversation, but be prepared to be real and spontaneous in the conversation. This sounds paradoxical – isn’t life that way! If there are things to prepare, do so (e.g. researching the facts, assessing what specifically is bothering you) – however, don’t be attached to that agenda. Rather let the conversation and collaboration lead the way.
  2. Initiate: Open your conversation, remind each other of your shared goal(s) and working relationship.
  3. Discuss: In the book “Crucial Conversations” they give a methodology called STATE:
    1. Share your facts
    2. Tell your story
    3. Ask for their view
    4. Talk tentatively
    5. Encourage testing
  4. Set your intention on whom you want to be in the conversation (e.g. servant leader, open, authentic, brave).
  5. Conclusion: Summarize and paraphrase agreements, disagreements and action steps. Acknowledge them for their contributions to the conversation.

Last tip: When a conversation is turning contentious because we don’t feel understood or the other person is frustrated, it may be time to humble ourselves and honor the others’ need to be heard is greater than our own.

“Unless someone like you cares a whole awful lot, nothing is going to get better. It’s not”. ~ Dr. Seuss

So, what is your leadership learning edge? What is the conversation you have been avoiding? What is stopping you from having it? When will you have the conversation that really matters?

We look forward to hearing from you and to having courageous conversations that matter!

Here is to you and your learning as a leader!

Lori and James

James Jackman & Lori Heffelfinger

310-543-7632 office |


Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson

Back to All Posts

How to Make Cool Leaders Great and Great Organizations Better.

Download our free guide

61d727e911249 (1)