What the Fundraising - Episode 290: A Fresh Look at Planned Giving with Tess Conrad

Host: Mallory Erickson
Guest: Darian Rodriguez Heyman
Date: April 7, 2026

Episode Overview

This episode of "What the Fundraising" brings together host Mallory Erickson and sector expert Darian Rodriguez Heyman for a wide-ranging discussion on technology, responsible AI adoption, and the deeply human roots of effective fundraising. While originally described as a "Fresh Look at Planned Giving," the episode is a masterclass on how nonprofit organizations can simultaneously honor their values, harness emerging tools like AI, and reframe fundraising for impact, confidence, and partnership. This episode is essential listening for nonprofit leaders striving to navigate the pressures of modern fundraising, technological change, and the ongoing challenge of connecting authentically with donors.

Key Discussion Points & Insights

1. Reframing Fundraising: "Pouring or Drinking?"

• Darian opens with a powerful analogy (based on a story from Mallory’s workshops) that reframes fundraising as an act of "pouring" — nurturing and channeling resources for impact, not "drinking."
  • “We are not the drinkers. Every single one of us...we are the pourers, we are the nurturers of society.”
    —Darien Rodriguez Heyman [00:57]
• The language and mindset around fundraising should shift from "begging" to "inviting," centering mutual vision and alignment, not personal rejection.
  • “People don’t give to you, they give through you.” [00:57, 34:22]

2. AI as a Tool, Not a Threat

• AI as a Force Multiplier: Responsible AI adoption can finally deliver on the nonprofit sector’s dream of personalized, relationship-based fundraising at scale.
  • “As we enter this age where we've left the era of planning and entered the age of navigation...responsible AI can absolutely help...mass personalization and audience segmentation.”
    —Darian Rodriguez Heyman [05:31]
• AI is not a replacement for relationships but a way to create more meaningful touchpoints and free up human capacity.
• AI brings both hope and overwhelm. Leaders must intentionally approach technology as a tool in service of mission, grounded in values.

3. Addressing AI Fears and Sector Realities

• Widespread Use, Little Strategy:
  • 92% of nonprofits use AI tools, but only 8% have an organizational strategy or policy. Most value accrues to "one or two" staff, with adoption being ad hoc and risky. [11:28]
  • “...Everybody is using AI within their organizations, but none of us have taken the time to come up with a concrete and cohesive...strategy...creates some pretty significant liability.”
    —Darian [11:28]
• Blockers:
  • Environmental impact, data security, algorithmic bias, job loss, and hallucinations are real concerns. The space lacks forums for open, values-based discussions about risks and safeguards.
  • “There was no talk about [these challenges] at the Nonprofit Technology Conference or at any of the conferences that are out there. It's all about how AI is going to help you raise more money or solve climate change or cure cancer, and not about...addressing people's fears and concerns…”
    —Darian [11:28]

4. The Order of Adoption: Must Start with Values

• Darian strongly advocates that the responsible AI adoption journey must begin with an authentic conversation about organizational and individual values, not just technical or functional considerations.
  • “You can't talk about responsible AI adoption until you talk about responsible. And what are the concerns about? Is this tool in line with our values to begin with?”
    —Darian [19:46]
• “Primer coat” before the “masterpiece”: Organizations should openly discuss and address concerns – whether solvable or not – before diving into use cases or product functionality.
  • “We cannot skip that primer coat.”
    —Darian [47:23]
• Mallory adds: embracing nuance helps individuals and organizations find their “conscious choice” for responsible use.
  • “I couldn't really understand responsible AI until I was using AI...wrestling with and grappling with the implications of the tool.”
    —Mallory [16:54]

5. Moving Adoption Forward: From Inspiration to Practicality

• The nonprofit sector is “over-inspired”—what’s lacking is tactical advice, not more “utopian” visioning.
  • “Enough with the inspiration...we want tactical, practical tips and tools. And do this, don't do that...”
    —Darian [26:30]
• Real-world examples and narrowly scoped tools are most effective: start “deeper vs. wider” rather than searching for all-in-one platforms.
  • “We help you fix that problem. Boom. You want to have better donor conversations. They start at practice.”
    —Darian (re: Practivated example) [43:04]

6. Foundation and Funder Perspectives

• Foundations are further along with AI for internal operations, but sector-wide capacity-building is lagging.
  • Only a few major funders are collaborating on field-wide support (e.g., the Fun AI initiative, MacArthur Foundation, etc.) [37:58]
• There’s a growing need for funders to support grantee AI adoption with resources, coaching, and technical assistance.

7. Nonprofit Tech Product Messaging: Features vs. Benefits

• Most effective technology providers emphasize outcomes for users over platform features or history.
  • “Lead with solving the problem and be really clear about it. And so I think, especially where the technology is at right now, your instincts have practivated, which is: deeper versus wider.”
    —Darian [43:04]
• The bigger issue is not tech company marketing, but sector education and conference content focusing on vision and fear-mongering over concrete, applicable use cases and solutions.

Notable Quotes & Memorable Moments

“We are the pourers, we are the nurturers of society...people don't give to you, they give through you.”
—Darian Rodriguez Heyman [00:57, 34:22]

“Responsible AI can absolutely help...it gets us a lot closer to that goal of mass personalization and audience segmentation and being able to have lots of individual discussions and relationships that we're properly nurturing and investing in.”
—Darian Rodriguez Heyman [05:31]

“For all the talk about AI...everybody is using AI within their organizations, but none of us have taken the time to come up with a concrete and cohesive and integrated strategy.”
—Darian Rodriguez Heyman [11:28]

“We cannot skip that primer coat… That’s something that we need to be doing a better job at at these nonprofit conferences, in books like mine, in these educational fora where we’re really starting with the AI for good 101.”
—Darian Rodriguez Heyman [47:23]

"I couldn't really understand responsible AI until I was using AI...wrestling with and grappling with the implications of the tool..."
—Mallory Erickson [16:54]

Key Timestamps

• [00:57] The "pouring or drinking" fundraising mindset shift
• [05:31] The promise of AI: mass personalization for nonprofits
• [07:31] Overwhelm, turbulence, and responsible AI as a solution
• [11:28] Adoption stats: 92% using AI, but only 8% have policies — risks and the value of open conversations about fears
• [19:46] Responsible adoption: starting with values first, not features or outcomes
• [26:30] Inspiration vs. tactical, practical advice — sector needs
• [34:22] The "begging for alms" vs. partnership/invitation approach 
• [37:58] Foundations & funder sector progress with AI
• [43:04] Features vs. benefits in nonprofit tech product messaging
• [47:23] The need for a “primer coat” — grounding in reality before implementation

Actionable Takeaways

• Begin with Values: Before implementing any AI tool, lead intentional and honest organization-wide conversations about mission alignment, ethics, and risks.
• Move Beyond Utopian Visioning: Demand and create more tactical, step-by-step guidance on how to use AI for specific, real-world nonprofit challenges.
• Focus Messaging on Solutions: Tech products should prioritize real, narrow solutions to specific problems, rather than generic "AI-powered" promises.
• Advocate for Sector-wide Support: Funders and associations should invest in field-building and practical training so the benefits of new technology are distributed equitably.
• Normalize Dialogue about Risks: Encourage open discussion of real concerns (environmental, data, bias, job loss) — this is prerequisite to meaningful adoption.

Further Resources

• Darian Rodriguez Heyman’s Book: AI for Nonprofits (Available on Amazon, Barnes & Noble)
• Free AI Coaching & Tools:
  • Helping People Help — Contact Darian, download the AI Prompt Engineering Cheat Sheet, schedule a free 20-minute coaching session
  • AI for Nonprofits (.org) — Sector events, resources, and learning labs
• Podcast Host/Programs:
  • Mallory Erickson’s Power Partners Program

This summary captures the key themes, expert advice, and practical steps discussed in the episode, highlighting the guest’s wisdom and actionable frameworks for the nonprofit sector at this moment of technological and ethical transformation.