Behind the Ask: Navigating Your First Major Gifts Role

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The journey from behind-the-scenes prospect researcher to frontline major gift officer can feel like jumping into the deep end without a life vest. In this illuminating conversation, Matt Stokes, Leadership Giving Officer at Yale University, shares his experience making this challenging career transition and the lessons he's learned along the way.
Matt brings a unique perspective, having spent years analyzing data and identifying prospects before stepping across the table to build relationships with donors directly. He reveals how his background in research has shaped his approach to cultivation and solicitation, providing him with valuable insights that many fundraisers never develop. Most importantly, he discusses the mindset shifts required when moving from data analysis to relationship building – particularly the realization that donors genuinely want to make meaningful impacts through their philanthropy.
Professional development emerges as a crucial theme throughout our conversation. Matt credits scholarships from organizations like AFP and CASE with providing essential learning opportunities when organizational budgets might have limited his growth. He emphasizes the transformative power of mentorship, sharing how two influential leaders in the fundraising community have shaped his career trajectory through their guidance and wisdom. For those early in their fundraising careers, he offers practical advice on finding mentors and accessing professional development, even with limited resources.
Perhaps most valuable is Matt's advice on building confidence in donor conversations, particularly for those new to making solicitations. He reframes these potentially intimidating encounters as opportunities to help donors achieve their philanthropic goals – a perspective that transforms the entire relationship dynamic. His insights on handling donor criticism demonstrate emotional intelligence that fundraisers at any career stage can learn from.
Whether you're considering making the leap into major gifts, are new to frontline fundraising, or are looking to build stronger bridges between your research and development teams, this conversation offers practical wisdom from someone who has successfully navigated this critical career transition.
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Chapters

1. Behind the Ask: Navigating Your First Major Gifts Role (00:00:00)

2. Welcome to Making the Leap (00:00:05)

3. Matt Stokes: From Research to Frontline (00:09:17)

4. The Importance of Professional Development (00:15:24)

5. Building Community Through AADO Conference (00:21:56)

6. The Confidence to Make the Ask (00:26:35)

7. Bridging Research and Fundraising Roles (00:32:51)