What the Fundraising – Episode 258: A New Paradigm: A Preview of the FundraisingAI Global Summit with Woodrow Rosenbaum

Release Date: September 11, 2025
Host: Mallory Erickson
Guest: Woodrow Rosenbaum (GivingTuesday)

Episode Overview

This episode previews the upcoming FundraisingAI Global Summit, focusing on how AI is transforming the nonprofit sector. Mallory Erickson and guest Woodrow Rosenbaum discuss how nonprofits can engage with AI meaningfully, ensuring a people-first approach, fostering innovation, and developing responsible governance. They explore the opportunities and challenges of AI adoption, address ethical concerns, and highlight actionable strategies and mindsets for sector leaders.

Key Discussion Points & Insights

1. Centering People, Not Just Productivity

• AI Hype vs. Core Purpose: Woodrow emphasizes the need to move beyond AI adoption for its own sake and instead ask, "What real problems are we solving?" ([06:27])

  "It's very easy to be like, thinking, I gotta get some AI as opposed to, what problem am I trying to solve? What is the right tool for solving that problem?" – Woodrow ([06:27])

• Efficiency vs. Productivity: The distinction between being truly efficient in advancing the mission versus just being busy is discussed ([04:41]).

  "If those boxes are not particularly efficient tasks towards achieving our mission, then it really is just productivity for productivity's sake." – Mallory ([04:41])

2. Overcoming Overwhelm and Fostering Engagement

• Sector-Wide AI Readiness: Many nonprofit professionals are experimenting with AI tools, often starting with simple productivity solutions to build familiarity ([02:23], [09:53]).
• Dealing with Overwhelm: The abundance of information can paralyze action. Mallory and Woodrow advocate for starting small, learning iteratively, and not being deterred by imperfection ([09:53]).

  "You're not going to be able to tackle everything all at once...if you have some basic building blocks, some key policies and frameworks...that's sufficient training wheels to then not worry about having to know how it all works all at once." – Woodrow ([09:53])

• Sessions at the Summit: The summit aims to address this overwhelm with sessions about self-care, working smarter, and managing discomfort with new tech ([12:06]).

3. Cultivating Cultures of Innovation and Navigating Fear of Change

• Innovation Requires Discomfort: Woodrow quotes Eugene Strickland:

  "Change is never good. Nothing good ever comes of it. And I think that's how a lot of people feel about change... getting comfortable with that discomfort is just a necessary component of any kind of change, any positive change requires." – Woodrow ([00:00], [13:44])

• Ethical Risks and Responsible Engagement: Avoiding or opting out of AI due to fear is impractical. Engaging with the technology is essential to navigating and addressing risks ([13:44], [16:12]).

4. Responsible and Beneficial AI Use

• Continuous Learning & Collaboration: The Fundraising AI (FAI) framework is highlighted as a guide for safe and ethical AI use, focusing on ongoing education rather than one-off compliance ([18:48], [26:36]).
• Team Peer Learning: Woodrow shares how internal, peer-driven learning environments (like AI-focused Slack channels) help lower the barrier to entry and foster experimentation ([17:40]).

  "It gives us a really easy peer learning environment where we can learn from one another and try things out in an environment where we have guidelines that can help us do that in a way that is safe." – Woodrow ([17:40])

5. Practical Tips for AI Adoption and Governance

• Start Small and Experiment: Both speakers stress the value of incremental learning—using productivity tools to build comfort, then expanding applications ([09:53], [24:23]).
• Prompt Engineering Is a Learned Skill: Being "bad at AI" is often just being new to prompt engineering; mistakes are part of the process ([22:15], [24:23]).

  "The best way to develop our skills is going to be by telling it to do something and seeing how it gets it wrong and revising our inputs..." – Woodrow ([24:23])

• Governance Should Enable, Not Just Restrict: Effective AI governance is about enabling responsible exploration, not merely prohibiting risky behaviors ([26:36]).

  "Governance as enabling an organization to do something responsibly and ethically as opposed to preventing an organization from doing things unethically or irresponsibly." – Woodrow ([26:36])

6. Leadership in a Dynamic AI Landscape

• Don't Wait for Clarity: Leaders are encouraged to engage now, as the AI field won’t settle into certainty; policies and internal learning groups are practical first steps ([29:27], [30:24]).

  "If you're waiting, you will always be waiting. It's not going to get any clearer. So find the place where you can start now." – Woodrow ([30:24])

7. Expanding Imagination: The Transformational Promise of AI

• Agentic AI and Inclusion: Woodrow shifts the conversation about AI's risks to its potential for expanding meaningful engagement, especially among under-invited communities ([32:42]).

  "I'd like to see that all people are afforded the opportunity to make positive change for themselves, their communities, and the world..." – Woodrow ([32:42])

• Equity Considerations: AI’s dangers around bias stem from existing human biases. AI offers the promise to deliver genuine, scaled personal engagement if sector values shift accordingly ([34:31]).

  "That inequity, the fact that more and more people are being left out of the nonprofit experience...that's us. We did that without any technological help." – Woodrow ([34:31])

• AI as Catalyst for Cultural Change: Rather than displacing responsibility, AI can spark needed discourse about sector values, purpose, and shortcomings ([36:43]).

8. Curiosity and 'What If' Thinking

• Embrace Curiosity Over Perfection: Mallory encourages leaders to bring “what if” questions and genuine curiosity to the summit and their work, using technology as a tool to solve longstanding challenges ([37:44]).

  "I hope people come to the summit with particular questions...but more than anything, I hope they come with a tremendous amount of curiosity and a lot of like, what ifs?" – Mallory ([37:44])

Notable Quotes & Memorable Moments

• On Change and Discomfort
  "Change is never good. Nothing good ever comes of it. And I think that's how a lot of people feel about change...getting comfortable with that discomfort is just a necessary component of any kind of change, any positive change requires." – Woodrow ([00:00], [13:44])

• On AI Use and Overwhelm
  "I'm concerned that we are going to use this technology in this environment to just improve efficiency. Well, right now, we're fewer people being asked, fewer people giving. Every year more and more concentration of the fundraising dollars into fewer and fewer hands. So if we're more efficient at doing that, we don't like that." – Woodrow ([34:31])

• On Leadership and Action
  "If you're waiting, you will always be waiting. It's not going to get any clearer. So find the place where you can start now." – Woodrow ([30:24])

• On AI Governance
  "Thinking about governance as enabling an organization to do something responsibly and ethically as opposed to preventing an organization from doing things unethically or, or irresponsibly." – Woodrow ([26:36])

• On the Transformational Opportunity
  "I'd like to see that all people are afforded the opportunity to make positive change for themselves, their communities, and the world." – Woodrow ([32:42])

Timestamps for Important Segments

• [02:23] – Discussion of sector adoption and engagement with AI
• [04:41] – Efficiency vs. productivity in nonprofit AI use
• [09:53] – Managing overwhelm and tips for responsible experimentation
• [13:44] – Tackling fear of change & fostering risk-ready, innovative cultures
• [16:12] – Balancing ethical concerns and the importance of sector-wide discourse
• [18:48] – Benefits of peer learning groups for AI adoption
• [22:15] – Mallory’s anecdote: “I feel like I'm bad at AI” and why that's normal
• [24:23] – Prompt engineering, iteration, and learning from failure
• [26:36] – Best practices for AI governance in nonprofits
• [29:27] – Leadership: why waiting for clarity is a trap
• [32:42] – Imagining the sector’s future: agentic AI and broadening impact
• [34:31] – Addressing equity gaps and underlying sector bias
• [37:44] – Encouragement to bring curiosity and “what if” thinking to AI adoption

Conclusion

This episode provides a grounded yet optimistic take on AI’s place in nonprofit fundraising and leadership, stressing curiosity, resilient experimentation, and the collective shaping of ethical frameworks. Listeners are encouraged to use AI to expand, not just expedite, their mission, and to leverage peer support and sector-wide discussion to drive both responsible practice and bold innovation.