Fundraising Series: Grow Your Major Gift Confidence – Strategies for Stronger Relationships & Bigger Asks

Are you ready to elevate your major gifts practice and step into donor conversations with clarity, confidence, and purpose? This workshop is designed to deepen your skills, strengthen your presence, and unlock larger, more meaningful gifts.

You will learn a practical, human-centered approach to major donor engagement that reduces anxiety, builds authentic connection, and leads to more successful asks. Through guided practice, real-world examples, and hands-on tools, you will learn how to:

  • Prepare for donor conversations with intention, grounding, and clarity
  • Strengthen your ability to listen deeply and connect with your donor
  • Ask powerful questions that reveal values, motivations, and readiness
  • Decide on what to ask for to make bold and meaningful asks that inspire giving
  • Follow up with donors to close a gift

Participants will walk away with renewed confidence, a sharper skillset, and practical frameworks they can use immediately to advance major gift relationships.

This is a supportive, interactive session designed to stretch your skills in a meaningful way to lead to more powerful donor conversations that create lasting impact.

This webinar is also a part of Common Good Vermont’s 2026 Fundraising Series. 

  • March 5, 1-2 pm: What’s Next for Fundraising? Trends, Technology, and Generational Shifts
  • March 10, 10am - 12pm: Designing High-Impact Annual Appeals
  • March 12, 10am - 12pm: Grow Your Major Gift Confidence – Strategies for Stronger Relationships & Bigger Asks
  • March 17, 10am - 12pm: To Campaign or Not to Campaign – Assessing Campaign Readiness
  • March 18, 10am - 12pm: How to Prospect – Finding Foundations to Fund You
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Virtual
Cost:
$40 for Members
$45 All Others
Presenter:
Jenn Hayslett

About the Presenter:

Jenn Hayslett brings 25 years of leadership experience as a successful fundraiser, manager, facilitator and trainer to her work as a coach and nonprofit consultant. Her engaging presentation style makes her a highly-rated trainer and presenter. 

Jenn has direct experience in all areas of fundraising and marketing for small to mid-sized nonprofits including annual funds, major gift solicitation and stewardship, capital campaigns, grant writing, community organizing, and volunteer management. Her specialty is in building and improving relationship-based fundraising programs. 

Jenn Hayslett is a certified trainer and facilitator and received her coach training through Coaches Training Institute (CTI). She has a consulting certificate in Diversity, Equity, Inclusion and Belonging from the Institute of Nonprofit Practice.  

You are welcome to visit Jenn Hayslett Coaching & Consulting for more information about Jenn and her work.