Detroit Philanthropy Guest blog by: Michelle Gilbert, CEO (Chief Engine Officer), Purple Engine Coaching & Consulting
There’s a particular kind of tension nonprofit leaders know well. It’s the quiet discomfort that surfaces before a board meeting, a volunteer check-in, or a donor conversation. The internal debate sounds familiar: “I should probably say something; just not today.”
The conversation might be about a board member who consistently misses meetings, dominates discussion, or resists necessary change. It might involve a volunteer whose approach no longer aligns with what the organization needs. Or a well-intentioned donor whose expectations are beginning to influence decisions in ways that create misalignment.
These are people deeply committed to the organization. People who care. People who have given their time, energy, resources, or influence. And yet, when certain behaviors go unaddressed, progress slows and friction builds behind the scenes.
So the leader waits. Not because they don’t see the issue. Not because they don’t care. But because the stakes feel high.
In mission-driven work, relationships carry weight. History matters. Gratitude matters. And raising a difficult issue can feel risky, especially when everyone involved believes they’re working toward the same goal.
But avoiding the conversation doesn’t keep things neutral. Over time, it erodes trust—sometimes before anyone realizes what’s happening.
Why These Conversations Get Avoided
In nonprofit organizations, avoidance is usually rooted in good intentions. Leaders worry about damaging relationships they depend on. They don’t want to appear ungrateful to board members who govern, volunteers who give generously of their time, or donors whose support makes the work possible.
There’s also the hope that things will resolve on their own. That a pattern will correct itself. That silence will buy time.
Instead, silence creates something else: misalignment, frustration, and confusion.
Others notice. Board dynamics shift. Volunteers grow uncertain about expectations. Staff experience the ripple effects. Decisions slow down. Accountability becomes uneven.
The issue doesn’t disappear. It becomes harder to address.
The Hidden Cost of Not Saying Anything
When leaders delay tough conversations, they usually absorb the impact themselves by adjusting plans, compensating for gaps, and managing around issues others feel but don’t name.
Left unaddressed, this creates strain toward both the individual involved and the role of leadership itself. What begins as an effort to preserve relationships can result in:
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Unclear expectations
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Lower trust across key relationships
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A culture where issues are discussed around the edges, but never directly
And perhaps most importantly, avoidance sends an unspoken message: some issues are too uncomfortable to address. That message rarely aligns with the values nonprofits stand for.
A More Human Way to Approach the Conversation
These conversations don’t require confrontation or heavy-handed authority. They require intention, respect, and clarity.
One of the most helpful shifts leaders can make is to stop focusing on what they need to say and start with why the conversation matters.
A grounded approach includes three principles:
Lead with shared commitment.
Anchor the conversation in what you both care about: the mission, people served, and responsibility you share. This frames the discussion as stewardship, not criticism.
Name impact, not intent.
Most board members, volunteers, and donors mean well. Focusing on impact – what’s happening as a result of certain behaviors – keeps the conversation factual and forward-looking, rather than personal or accusatory.
Be clear about expectations going forward.
Clarity protects relationships. When expectations are explicit, people have a fair opportunity to adjust and contribute in ways that truly support the organization.
Handled thoughtfully, these conversations can strengthen relationships rather than strain them. Many leaders are surprised to learn that concerns they’ve been quietly managing were being felt by others; they just hadn’t been named.
Why This Matters More Than Ever
Nonprofit work is complex. Resources are stretched. Expectations are high. And leadership often means holding competing realities at once.
Avoiding hard conversations may feel easier in the moment, but it rarely serves the mission over time. Addressing them with clarity and care builds healthier boards, more aligned volunteers, stronger donor partnerships, and cultures where accountability and trust can coexist.
The question isn’t whether difficult conversations will arise. They will. The real question is whether leaders feel equipped and supported to have them.
If there’s a conversation you’ve been postponing, it may be worth asking: What would change if I approached this with honesty, respect, and a shared sense of purpose?
That’s where progress begins.
About the Author
Michelle Gilbert is founder and Chief Engine Officer of Purple Engine Coaching & Consulting LLC. She works with leaders to navigate difficult conversations, strengthen professional relationships, and lead with greater clarity and confidence, especially in moments that feel high-stakes.
For leaders looking for a practical next step, Michelle offers a free exercise, 4 Ways Strong Leaders Navigate Difficult Conversations, designed to help leaders approach tough discussions with intention, confidence, and care.
You can learn more at Purple Engine Coaching or follow Michelle on LinkedIn for insights on navigating leadership challenges and preparing for difficult conversations.