The Lady Whistledown of Nonprofit Transformation – Part 3

“Dearest gentle readers, it has come to this author’s attention that society has begun to anticipate these very papers with such fervor that their mere arrival shapes the conversation before a single word is read. One must wonder: when influence becomes expectation, how does one wield such power to elevate rather than merely entertain?”

Eventually, everyone knew to expect Lady Whistledown’s society papers. Her reputation preceded her into every drawing room, every social gathering, every whispered conversation. When you become known for transformation in the nonprofit sector—when your “papers” start reshaping how organizations think about culture, belonging, and change—you face a delicious dilemma: How do you use that growing influence to create even deeper, more systemic change?

The Double-Edged Sword of Success

There’s a peculiar moment in every transformational leader’s journey when you realize people are no longer just hiring you for what you do—they’re hiring you for who you’ve become. Your reputation starts opening doors, but it also creates expectations. Suddenly, you’re not just “Sarah who helped with our fundraising culture”; you’re “the fundraising transformation expert” who’s expected to have revolutionary insights at every conference, brilliant solutions to every challenge, and somehow, the ability to transform organizations just by showing up.

One leader I know describes it this way: “I used to walk into organizations as a collaborator. Now I walk in as ‘the expert,’ and everyone’s waiting for me to perform magic tricks instead of doing the work together.”

This is the blessing and burden of becoming Lady Whistledown—your influence grows exponentially, but so does the temptation to stay safely within your greatest hits rather than pushing into more complex, systemic territory.

Beyond Your Greatest Hits

Lady Whistledown could have continued indefinitely with the same formula: society gossip, romantic entanglements, seasonal scandals. But her true power emerged when she used her platform to expose deeper truths about power, class, and social justice. Similarly, transformational leaders reach their highest impact when they leverage their reputation to tackle challenges beyond their original expertise.

Consider the evolution I’ve witnessed in my own work. The Wingspan Method began as a response to nonprofit fundraising dysfunction—organizations treating donors as ATMs rather than partners, development teams isolated from program work, and cultures that celebrated individual heroics over collective success. But as the approach gained recognition, something interesting happened: organizations started asking deeper questions.

“If we can transform our fundraising culture, why can’t we transform our entire approach to power and decision-making?”

“If the Wingspan Method works for donor relationships, what would it look like applied to board governance?”

“If you can help us create belonging in development, can you help us address the racism embedded in our programming choices?”

The reputation that started with fundraising transformation became a platform for systemic organizational change. And with that expansion came both opportunity and responsibility.

The Responsibility of Influence

When your “society papers” start shaping sector-wide conversations, every choice becomes more consequential. Do you stay in your lane, continuing to solve the problems you’ve already proven you can address? Or do you use your platform to push the sector toward harder, more necessary conversations?

Lady Whistledown faced this choice when she could have continued focusing on romantic drama but instead chose to expose deeper social injustices. The nonprofit sector faces similar inflection points: Will we use our growing understanding of transformation to address surface-level symptoms, or will we dig into the systemic issues that create those symptoms in the first place?

Here’s what I’ve learned about wielding influence responsibly:

1. Use Your Platform to Amplify Voices, Not Just Your Voice

The most dangerous trap of reputation is believing your own press. When organizations start calling you “the expert,” it’s tempting to center every conversation around your methodology, your insights, your solutions. It’s why I shrug when people call me an expert and I say, I’m just in it with you and want to keep learning, too.  True transformation happens when you use your platform to elevate the wisdom that already exists within communities—particularly voices that have been systematically marginalized.

One of my most powerful recent experiences involved working with a nonprofit whose Board & staff leadership was largely white while serving an extraordinarily diverse community.. Instead of imposing the Wingspan Method as the solution, I used my platform to create space for community members to share their expertise about what transformation actually looked like from their perspective. My role became facilitation and amplification rather than prescription.

2. Stay Curious About Your Own Blind Spots

Reputation can insulate you from feedback. When people see you as “the transformation expert,” they’re less likely to challenge your assumptions or point out your mistakes. This is dangerous for any leader, but particularly dangerous for those working on issues of equity and systemic change.

I’ve started building what I call “reputation reality checks” into my practice: working with advisors who are comfortable challenging my thinking, seeking feedback from communities most impacted by the work, and regularly examining whether my approaches are actually creating the changes I claim to champion.

3. Use Success to Take Bigger Risks

The safety that comes with reputation creates space for experimentation. When people trust your track record, they’re more willing to try approaches that feel uncertain or unconventional. This is where transformational leaders can push beyond incremental change toward systemic transformation.

Recently, I’ve been using the credibility built through fundraising transformation work to advocate for more radical approaches to nonprofit governance, resource distribution, and power-sharing. These conversations wouldn’t have been possible early in my career, but reputation creates room for necessary risk-taking.

The Evolution of Your “Papers”

Lady Whistledown’s society papers evolved from entertainment to social commentary to calls for justice. As your influence grows, your content—whether that’s blogs, speaking engagements, consulting work, or organizational leadership—has the opportunity to evolve toward deeper impact.

Early career influence often focuses on:

  • Solving discrete problems
  • Improving existing systems
  • Helping organizations work better within current paradigms

Mature influence can tackle:

  • Questioning the systems themselves
  • Shifting sector-wide conversations
  • Creating new paradigms rather than optimizing old ones

This doesn’t mean abandoning your core expertise—it means using that expertise as a foundation for broader systemic change. The fundraising transformation work doesn’t disappear; it becomes a case study for what’s possible when organizations fundamentally reimagine how they operate.

Your Legacy Toolkit

Ready to use your growing influence wisely? Consider these strategic approaches:

The Platform Audit: List everywhere your voice currently has influence—board positions, speaking opportunities, social media platforms, consulting relationships. For each, ask: “Am I using this platform to maintain status quo conversations, or to push toward necessary change?”

The Amplification Practice: In your next three professional presentations or written pieces, intentionally center voices other than your own. Quote community members, cite leaders from marginalized communities, share credit explicitly.

The Risk Assessment: What’s one systemic issue you care about but haven’t addressed publicly because it feels too risky or outside your expertise? Your reputation might create enough safety to start those conversations.

The Legacy Question: When people tell stories about your influence five years from now, what do you want those stories to be about? What change do you want to be known for catalyzing?

The True Power of the Pen

Lady Whistledown’s ultimate revelation wasn’t about who she was—it was about what she chose to do with her influence. She used her platform not just to expose secrets, but to reshape what society valued. She challenged power structures, elevated overlooked voices, and created space for different kinds of stories to be told.

In the nonprofit sector, we have a similar opportunity. Those of us who’ve built influence through transformation work can use that platform to shift sector-wide conversations from transactional to relational, from exclusive to inclusive, from leadership over people to leadership with people.

The question isn’t whether your reputation will precede you—if you’re doing transformational work, it inevitably will. The question is what you’ll do with the influence that reputation creates.

The Final Society Paper

Here’s what I want to be known for: not just helping individual organizations fundraise better, but helping the entire nonprofit sector understand that transformation is possible when we’re willing to examine our assumptions, share power authentically, and center the voices of those most impacted by our work.

The Wingspan Method isn’t really about fundraising—it’s about creating organizational cultures where everyone belongs, where power is shared rather than hoarded, and where transformation happens through relationship rather than mandate. It’s about proving that another way is possible.

And like Lady Whistledown’s final society paper, the most important revelation might be this: the secrets weren’t the point. The point was using the truth to create a better world.

What secrets is your organizational culture keeping? And more importantly, what would change if you had the courage to address them? I’d love to continue this conversation—share your thoughts on LinkedIn or drop me a note. Together, we can help the nonprofit sector move from keeping secrets to creating cultures where transparency, belonging, and transformation aren’t just values on the wall, but the foundation of everything we do.

The society papers are written. The question now is: what story will you help write next?