The Art of the Ask

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About this Video 

This 90-minute masterclass is built around a single, counterintuitive premise: that the most powerful fundraising tool a development professional possesses is not their proposal, their data, or their access. It is their belief. Drawing on a personal story involving an unlikely ask to Joni Mitchell, this curriculum guides participants through six interconnected modules that address the full arc of donor engagement: from the psychology of persuasion and the role of authentic conviction, to the strategic use of storytelling, the architecture of a great ask, and the art of handling no with grace. Each module is grounded in real-world practice and designed to shift not just how participants ask – but how they think about asking. This curriculum is designed for advanced development professionals – major gift officers, campaign directors, and senior fundraisers – who are ready to move beyond transactional techniques and into a deeper, more human-centered practice.

About the Instructor

Timothy Boynton is a nationally recognized healthcare executive, strategic communicator, and one of the most accomplished fundraisers in the field today. With more than 20 years of experience in philanthropy and development, he has raised over $225 million throughout his career both in philanthropy and producing, leading transformational campaigns that have reshaped access to care and strengthened the communities they serve. Before transitioning into healthcare philanthropy, Tim began his career in the entertainment industry, working on Broadway and in theatrical production alongside some of the industry’s most respected creatives. That foundation in storytelling continues to define his work today, shaping how he engages donors, inspires teams, and communicates vision at the highest levels.

 

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