Podcast Summary: "A Volunteer’s Guide to Major Donor Conversations"

Nonprofits Are Messy with Joan Garry | Ep 247
Guest: Eileen Opatut | February 14, 2026

Episode Overview

In this insightful and candid episode, Joan Garry invites her wife, Eileen Opatut, Emmy Award-winning television executive and volunteer fundraiser, to discuss in detail her journey into major donor fundraising for Lambda Legal’s National Leadership Council. The episode centers on demystifying how non-development professionals—especially volunteers—can successfully engage in high-stakes, relationship-based fundraising. Through real stories, practical advice, and honest reflections, Joan and Eileen dismantle the fears and misconceptions tied to "the ask," offering listeners an authentic, step-by-step guide for initiating, conducting, and growing major donor conversations.

Key Discussion Points & Insights

1. The “Why” of Volunteering and Fundraising

Timestamp: 03:55–06:31

• Eileen shares her motivation: personal commitment to Lambda Legal after the organization's earlier support for her own family, combined with her drive to not stand idly by as LGBTQ rights are threatened.
• Fundraising felt necessary: “I couldn't overcome my fear of what would happen if I didn't raise the money.” (Eileen, 04:05)
• For non-attorneys, fundraising is the main volunteering path at Lambda.

2. Preparation Without a Handbook

Timestamp: 06:45–09:24

• Eileen received no official training; she self-educated by researching Lambda Legal, current events, and nonprofit fundraising basics.
• She felt insecurity about answering detailed questions, but Joan advised: "You know what? I don't know the answer to that question, but I will check into it and get back to you." (Eileen, 08:56)
• Emphasis on being “ridiculously prepared” is common, but humility and honesty go further.

3. Building a Prospect List: Beyond the Usual Suspects

Timestamp: 09:58–14:53

• Eileen describes herself as solitary, not a natural networker, lacking a vast contact list.
• Her approach: List people with “skin in the game,” such as those with LGBTQ family, friends, or personal connections—even discovering leads through candid conversations.
• Memorable insight: “You have to talk about it. ... someone says, so what's new, Eileen? I'll...always say, well, you know, what's really keeping me busy lately is I'm raising money for Lambda, and here's why.” (Eileen, 12:12)
• Tips on leveraging social introductions to expand warm leads.

4. Making the Ask: The Art of Emailing and First Conversations

Timestamp: 16:25–19:57

• Eileen personalized her outreach, referencing shared contacts and organizational leadership.
• Joan's advice: “Just say you want to talk. Don't say, I am calling you because I want to...open up your checkbook.” (Joan, 16:31)
• Importance of positioning: Sharing how Joan and Eileen think about their own giving models donor behavior without making it about the money first.
• Some prospects were newer to giving, thus required nurturing, explanation, and hands-on engagement.

5. Determining How Much to Ask For (and Multi-year Gifts)

Timestamp: 22:33–25:12

• Together, they strategized specific ask amounts. Eileen’s first ask (“they said, oh, sure, great”) felt both validating and like maybe she “should have asked for more.” (Eileen, 22:33)
• Advocated for multi-year commitments: “Lamda really needed to be able to count on a certain amount of money coming in so that they could replace the pro bono legal services that they had started being denied.” (Eileen, 24:03)
• Multi-year gifts benefit both donor and organization and create “ego points” for donors, making them feel impactful.

6. Handling Rejection, Crickets, and Emotional Pitfalls

Timestamp: 32:16–36:53

• Eileen grapples with “crickets” (non-responses), feeling “surprised” and “a little bit” personally hurt.
• Joan’s perspective: “Do you think everything is about that email for that person?... They're just lapsed because they have lives.” (Joan, 33:41)
• Fundraisers must separate friendship from transactions, embrace rejection as rarely personal, and remain persistent without pestering.
• “I'm giving them an opportunity to get involved in something they care about—or they should care about.” (Eileen, 36:10)

7. Listening, Learning, and The Follow-Up

Timestamp: 38:39–41:27

• Eileen learns not all thoughtful, affluent people have a “giving plan”—so offering options and frameworks can be a key value-add.
• The hesitation moment: Giving the number and waiting for a response. Joan’s script for follow-up: “I'd like you to give me some permission to follow up with you. If I don't hear from you, what would you suggest?”

8. Preparing for a Tough Ask: Meeting with Seasoned Fundraisers

Timestamp: 41:48–44:32

• Eileen prepares differently for a Zoom with a top prospect—including both an attorney and an experienced fundraiser.
• New tactic: Offer to provide information in advance, but ask what the donor wants to see, empowering their engagement and not assuming needs.

9. Top Lessons and Final Advice for New Volunteer Fundraisers

Timestamp: 45:04–50:33

• Key takeaway: “If I can do it, so can anyone. ... It took a long time for me. I hesitated. ... But once you start, the connective tissue is all there, and one thing leads to another...” (Eileen, 45:04)
• Be organized in tracking asks and follow-ups.
• Detach ego: They’re giving to the cause, not you personally.
• “It's really like you're selling something. And if you care about that something...I think that it will be fine.” (Eileen, 46:28)
• When in doubt, plot out dedicated times for fundraising tasks to break through procrastination.

10. The Power of Storytelling and Credibility

Timestamp: 47:36–49:18

• Narrative is crucial—facts are important, but stories are what move people.
• “Best storyteller ever. And once you tell a story about the topic that you care about, it's what is going to strike a chord with the person you're talking to.” (Eileen, 47:58; affirmed by Joan)
• Closing reminder: “Credible messenger plus compelling story equals a new [donor/supporter].” (Joan, 48:34)

Notable Quotes & Memorable Moments

• “I couldn't overcome my fear of what would happen if I didn't raise the money... you can't win if you don't fight.” —Eileen, 04:05
• “The people I call on are usually pretty well informed... it was just fine to be able to say, 'You know what? I don't know the answer to that question, but I will check into it and get back to you.'” —Eileen, 08:56
• “You have to talk about it. You have to actually bring that up with people and say, you know, this is something I am involved in and doing.” —Eileen, 12:12
• “Going in with a number in your head and making a very specific ask are two really important components of successful fundraising. But... listening [is just as important].” —Joan, 38:10
• “I'm really not the perfect candidate to be a fundraiser. But if I can do it, so can anyone.” —Eileen, 45:04
• “My passion for the mission of GLAAD is greater than my fear of asking or hearing no.” —Joan, 30:36 (on her motivational index card)

Timestamps for Key Segments

| Timestamp | Topic/Segment | |------------|-----------------------------------------------| | 03:55 | Eileen’s motivation and choosing Lambda | | 06:45 | How Eileen prepared herself | | 09:58 | Prospect list: who, how, and why | | 12:12 | Socializing your cause & networking naturally | | 16:25 | Writing the first ask email | | 18:53 | Handling positive but inexperienced prospects | | 22:33 | Deciding how much to ask; the multi-year gift | | 32:16 | Coping with non-responses (“crickets”) | | 38:39 | The art of listening and follow-up | | 41:48 | Getting ready for a big ask | | 45:04 | Lessons learned and final advice | | 47:36 | The importance of storytelling |

Practical Takeaways for Listeners

• You don’t need a massive network or fancy title to be a successful volunteer fundraiser—courage, curiosity, and organization are your best tools.
• Be honest when you don’t know something; authenticity builds trust.
• Fundraising is rarely a solo act; mentors and partners (even spouses!) are invaluable.
• Turn everyday conversations into opportunities by sincerely sharing your cause.
• Ask specifically, follow up tactfully, and detach your self-worth from the outcome.
• Storytelling is your greatest asset—facts motivate, but stories inspire.

Tone/Mood Notes:
The conversational dynamic is warm, direct, and encouraging, with flashes of humor and authentic vulnerability. The episode is packed with practical advice, real scripts, and reassuring reminders for fundraisers at any level.

This summary is designed for nonprofit professionals seeking actionable strategies for donor conversations, especially those new to volunteer or peer fundraising.