Making the Confident Ask (on Zoom)

*Making the Confident Ask: How Nonprofit Leaders Successfully Request Donations and Mobilize Fundraising Teams

Asking for a donation is one of the most important and most avoided responsibilities in nonprofit leadership. Many organizations struggle not because people don’t care about the mission, but because staff, board members, and volunteers lack the confidence, structure, and language needed to make effective fundraising requests. 

This 2-hour, highly interactive workshop focuses on the essential skills leaders need to confidently ask for donations while staying organized when multiple people are involved in fundraising. Participants will practice real conversations, learn simple tools for deciding what to ask for, and explore practical ways to track donor relationships without complicated systems.

The session is designed to be hands-on and realistic for busy nonprofit leaders. Participants will spend time in guided practice, small-group role play, and real-life scenarios so they leave with language they can use immediately. 

Topics Covered

• Why asking for donations feels uncomfortable — and how to move past it
• The basic structure of a successful donation request
• How to decide what to ask for based on relationship, interest, and capacity
• Practice conversations and role-play to build confidence asking for support
• How to involve board members and volunteers in fundraising without confusion
• Simple ways to track prospects, assignments, and follow-up using basic tools
• Keeping fundraising organized when multiple people are making asks
• Setting realistic expectations for volunteer involvement in fundraising 

Participants will leave with:

• Sample language for making a donation request
• A simple framework for deciding ask amounts
• A basic system for tracking donors and volunteers
• Greater confidence in leading fundraising conversations 

This workshop is ideal for Executive Directors, Board Members, Fundraising Committee Members, and volunteers who are expected to help ask for donations but have never been trained how.

Cindy Hales, Ed.D. is the Vice President of Community Investment at the Capital Region Community Foundation. There she leads the team responsible for the foundation’s grant making, nonprofit capacity building, and scholarship coordination. She has served in that role since 2018.

Prior to joining the foundation, Cindy spent 18 years as a fundraiser working in higher education and healthcare, where she participated in multimillion-dollar campaigns. She strongly believes that successful fundraising requires good planning, thoughtful strategy, and genuine commitment to helping donors fulfill their charitable interests.

Cindy holds a doctorate in Educational Leadership from Central Michigan University. She has also served on countless nonprofit boards. In her spare time, Cindy is an avid reader who currently leads her women’s book club and loves tending to her backyard garden. But her passion is travel! Cindy is eagerly planning out the details of her 2026 safari to Tanzania.

Nonprofit Network's vision is to be a valued partner working alongside nonprofits and their leaders to transform
communities so that all people can thrive. 

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