95. Navigating Stakeholder Expectations and Building Sustainable Fundraising Strategies
About this episode
Have you ever felt the weight of balancing short-term fundraising goals with long-term organizational growth? As nonprofit leaders, we often find ourselves pulled in multiple directions—meeting board expectations, engaging donors, and ensuring our strategies align with mission-driven outcomes. It’s a lot. But here’s the good news: there’s a better way to approach this challenge.
In this episode of The Intentional Fundraiser podcast, I’ll share insights from my conversation with Cherian Koshy, a visionary in nonprofit leadership and fundraising innovation. Together, we’ll explore how curiosity, empathy, and strategic thinking can transform how we navigate stakeholder expectations, measure success, and leverage technology—all while staying true to our mission. By the end of this post, you’ll walk away with actionable strategies to create sustainable growth for your organization while fostering deeper connections with stakeholders.
The Power of Curiosity: Understanding Stakeholder Perspectives
One of the most profound lessons I learned from Cherian is the importance of starting with curiosity. Often, we assume that sharing best practices or data will automatically align stakeholders like board members or donors with our vision. But as Cherian pointed out, these individuals come from diverse lived experiences that shape how they make decisions.
For example, instead of asking “How do I convince my board to do this?” Cherian suggests asking “How does my board typically make decisions?” By understanding their criteria—whether it’s social proof or data-driven analysis—you can tailor your approach to meet them where they are. This shift in mindset fosters collaboration rather than conflict and ensures that everyone is working toward shared goals.
Curiosity isn’t just for external relationships; it’s equally vital internally. As fundraisers, we’re skilled at asking donors meaningful questions like “What inspired your most impactful gift?” Yet, when it comes to engaging our colleagues or leadership teams, we often forget to extend the same grace and curiosity. Building stronger internal relationships can lead to more cohesive and effective strategies.
Rethinking ROI: Beyond the Numbers
When it comes to measuring success, Cherian emphasized that return on investment (ROI) is critical but shouldn’t be the sole metric driving decisions. He likened nonprofits to living organisms—complex systems that require more than just financial metrics to gauge health.
For instance, while cost-to-raise-a-dollar is important, it doesn’t capture the intangible value of stewardship or relationship-building activities. As Cherian put it, “Not everything that matters can be measured, and not everything that can be measured matters.” Stewardship efforts like thank-you calls or personalized notes may not yield immediate revenue but are essential for long-term donor retention and trust.
Cherian also challenged us to move away from short-term thinking. Major gifts often take years to cultivate, yet many organizations evaluate success within a 12-month cycle. By extending timeframes and pairing short-term benchmarks with long-term goals—such as a three-year $9 million target instead of an annual $3 million goal—we allow room for meaningful relationship-building without sacrificing accountability.
Leveraging Technology Without Losing Human Connection
In an age where artificial intelligence (AI) and automation are transforming fundraising, Cherian offered a balanced perspective on technology’s role in our work. Tools like KindSight’s generative AI can streamline tasks like donor segmentation or report generation, freeing up valuable time for fundraisers to focus on building relationships. However, he cautioned against over-automation that risks dehumanizing donor interactions.
The key is using technology as an enabler—not a replacement—for human connection. Automating administrative tasks allows us to spend more time having meaningful conversations with donors or crafting personalized outreach strategies. As Cherian said, “Let the data do its thing so humans can focus on what they do best—building relationships.”
Let’s Build a Sustainable Future Together
Navigating stakeholder expectations and balancing short-term pressures with long-term goals isn’t easy—but it’s possible with curiosity, strategic thinking, and the right tools in place. By understanding your stakeholders’ perspectives, redefining how you measure success, and leveraging technology thoughtfully, you can create sustainable growth for your organization while staying true to your mission.
I’d love to hear your thoughts! How do you navigate these challenges in your organization? Share your experiences in the comments below—and don’t forget to pass this post along to colleagues who could benefit from these insights.
With boundless gratitude,
Tammy Zonker
Major Gift Expert & Keynote Speaker
Our guest
Cherian Koshy, Vice President of Product Strategy, Kindsight
LinkedIn / Twitter / Contact / Website
“Let the data do its thing so humans can focus on what they do best—building relationships.”
Cherian Koshy, Vice President of Product Strategy, Kindsight
Resources mentioned in this episode
Exactly What to Say by Phil M Jones
Procrastinate on Purpose: 5 Permissions to Multiply Your Time by Rory Vaden
Take the Stairs: 7 Steps to Achieving True Success by Rory Vaden
Thanks to our friends over at Kindsight for sponsoring this episode of The Intentional Fundraiser podcast.
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