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How Courageous Conversations Can Address the Elephant in the Room

"Courage is what it takes to stand up and speak; courage is also what it takes to sit down and listen." ~ Winston Churchill

As a new philanthropic executive for a local place-based foundation, helping our team launch a new community innovation grant was among my first responsibilities. The initiative promised to award a half-million-dollar grant to a local nonprofit for innovative work, generating palpable excitement among the foundation's board and staff. But the real shock came a few weeks later, during a coffee conversation with a nonprofit leader. He referred to our community innovation grant as "one of the worst ideas ever introduced into the community," likening it to the Hunger Games for nonprofits. He explained it encouraged a feeding frenzy type of competition rather than collaboration, which was not our intent. As it turned out, he wasn't the only one with this viewpoint; he was just the first to openly express what many were whispering behind closed doors in safe spaces. This leader’s willingness to have a courageous conversation and to address the elephant in the room proved to be a turning point in the foundation's community innovation grant process. The leader’s feedback led to our team changing our “winner takes all” community innovation process into a process that encourages meaningful collaboration that would lead to multiple investments in innovative partnerships and community change. Four lessons learned that are worth noting:

  1. Courageous Conversations are Essential for Innovation. Honest and open feedback is crucial for true innovation. Without the nonprofit leader's courage to express his views, we might have continued down a path that was inadvertently harming the non-profit sector and the communities we were committed to serving.

  2. Courageous Conversations Focus on Purpose Over Politeness. Successful leaders allow purpose to be the starting point for courageous conversations. When we focus on being polite in our conversations and not wanting to offend, our politeness can be a hindrance to us achieving our goal(s). Courageous conversations that are purposeful can lead to visionary and meaningful change.

  3. Transforming Criticism into Positive Change. The initial disappointment gave way to a powerful realization – that courageous conversations can provide valuable insights, and by listening, acknowledging, and addressing the issues, we can turn criticism into positive change. However, receiving feedback is only half the battle; as leaders, we need to ensure we're translating this feedback into actionable change to improve and innovate effectively.

  4. The Importance of Safe Space. The culture of an organization plays a significant role in whether individuals and partners feel comfortable voicing their concerns. Leaders need to ensure they're fostering an environment that encourages open dialogue. Creating a culture where stakeholders feel safe to voice their concerns openly can prevent potential pitfalls. By providing a safe space, leaders can address the "elephant in the room" before it wreaks havoc.


  1. Courageous Conversations Role-Play: Allow your team to split into pairs and role-play both sides of a difficult conversation. This will improve communication skills and also build empathy and understanding.

  2. Feedback Forum: Implement a regular forum where team members can share their thoughts and ideas without fear of judgment. This open dialogue can pave the way for innovative ideas and help identify potential issues before they escalate.

Questions Leaders Should Be Asking About Courageous Conversations

  1. What courageous conversations are you willing to have this week?

  2. How are we fostering a culture that encourages courageous conversations?

  3. What steps are you taking to turn feedback into actionable change?


We would love to hear from you!

Share your experiences on having courageous conversations in the comments below

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