AI and Its Influence on Charitable Planning

We are living in a transformative era of technology. It has been three years since the discovery of generative AI, a breakthrough reshaping the industry at a pace comparable to the rise of the internet in the 1990s. When the web became widely accessible in 1993, businesses began adopting email and websites en masse by 1996, forever changing how we operated. AI is poised to redefine how advisors, nonprofits, and donors interact and plan for the future.

For charitable planning professionals, AI offers unprecedented opportunities to enhance research, engage donors, and streamline complex processes. However, these benefits come with challenges, mainly when accuracy and reliability are paramount. Advisors must understand the tools at their disposal—generative AI, agentic AI, and systems trained on curated, trustworthy content—to use them effectively.

As the founder of Planned Giving Interactive (PGI), I’ve dedicated the past several years to creating solutions like Frank, an AI research strategist, and Max, a donor-facing chatbot, to help charitable professionals unlock the full potential of AI.

The Origins of Generative AI

Generative AI emerged from researchers’ efforts to improve natural language processing. Early developments focused on tools like autocorrect and predictive text, but creating large language models (LLMs) unlocked the ability to generate coherent responses from the bots at scale.

An unexpected breakthrough occurred when these models began to exhibit emergent properties, such as generating creative content and engaging in human-like conversations. Generative AI quickly advanced into a transformative technology capable of producing written content, code, and much more.

For charitable planning, generative AI enables professionals to simplify estate planning concepts, draft personalized donor communications, and enhance donor research. But to fully understand its potential, it’s essential to recognize its strengths and limitations.

Key AI Concepts for Advisors

Advisors working with AI should familiarize themselves with the foundational technologies driving its capabilities:

• Generative Pre-trained Transformer (GPT): The architecture behind tools like ChatGPT, designed to process and generate text.
  Example: Advisors can use GPT to generally compare tax implications for donor-advised funds (DAFs) versus charitable remainder trusts (CRTs).
• Machine Learning (ML): A subset of AI that improves performance by learning from patterns in data.
  Example: Advisors can use ML to proactively identify clients at risk of underutilizing tax-advantaged strategies (e.g., not maximizing charitable deductions or missing QCD opportunities). By analyzing historical behaviors, income patterns, and demographic indicators, ML models can surface timely planning opportunities—allowing advisors to deliver more personalized, anticipatory guidance.
• Natural Language Processing (NLP): AI designed to understand and generate human language.
  Example: NLP tools can summarize complex tax or regulatory documents for advisors.
• Prompt Engineering: Crafting specific instructions to achieve desired outputs from AI models.
  Example: An advisor could ask an AI to “Generate a 500-word explanation of Qualified Charitable Distributions (QCDs) for donors aged 70½ and older.”

The Future of Donor Websites: Inspired by Apple’s Minimalism

Generative AI is revolutionizing how donors and advisors interact with websites. Too often, nonprofit websites feel cluttered, forcing visitors to navigate page after page to find the necessary information. It’s a time-consuming experience, and often, information is outdated.

The websites of the future will draw inspiration from Apple’s retail philosophy. Like Apple Stores—sleek, minimalist, and intuitive—they will create a streamlined experience where visitors can quickly find what they’re looking for. Instead of countless pages of information, these websites will feature AI-powered tools capable of answering donor questions in real time.

Imagine a donor visiting a nonprofit’s website and asking: “How can I leave a legacy gift for cardiovascular research?”

The AI responds instantly with actionable options, such as using a QCD or funding a CRT tailored to the donor’s goals. This intuitive, conversational approach builds trust and deepens donor engagement.

Instead of wading through web pages, the AI tool instantly provides a clear, tailored recommendation. Seeking out nonprofit websites that embrace this interactive model will draw donors to their estate planning pages—just as Apple’s stores do—while leaving visitors with a sense of actionable clarity and purpose.

Agentic AI: A Proactive Partner for Advisors

Agentic AI is revolutionizing how financial advisors and estate planning attorneys operate by proactively analyzing data, identifying opportunities, and automating routine tasks. This technology helps professionals deliver more strategic, personalized, and efficient services.

For example, platforms like Conquest Planning’s Strategic Advice Manager (SAM) can analyze client data to construct comprehensive financial plans, saving time and offering proactive recommendations. Similarly, Wealth.com’s ‘Ester’, an AI-powered estate planning legal assistant, can read and summarize documents, enabling attorneys to manage complex estate plans more efficiently.

By automating tasks such as identifying tax-saving opportunities, preparing draft documents, or tracking client milestones, agentic AI tools allow professionals to focus on building stronger client relationships and delivering high-value strategic advice—the integration of these tools positions advisors and attorneys as forward-thinking leaders in their fields.

Max™ and Frank™: Tools Built for Estate Planning

AI’s effectiveness hinges on the data it’s trained on. General-purpose tools like ChatGPT rely on open internet datasets, which can lead to “hallucinations”—outputs that sound plausible but can be factually incorrect. In contrast, tools trained on contained, expert-vetted content are far more reliable for professional use.

At PGI, we developed Frank and Max to address this need. Both are trained on a curated 6–7-million-word database focused exclusively on planned giving, including IRS regulations, private letter rulings (PLRs), and the latest tax updates.

• Frank™ is a technical strategist designed for advisors. It provides precise, fact-checked answers to complex tax laws, charitable vehicles, and estate planning questions.
• Max™ uses the same curated data but translates it into plain English for donors. Instead of technical jargon, Max offers clear, conversational responses that guide donors through their giving options.

For example, if a donor asks Max about legacy giving, she might suggest: “You could fund a charitable remainder trust, which provides income during your lifetime and leaves the remainder to the nonprofit of your choice.”

This blend of accuracy and accessibility ensures that advisors and donors receive the insights they need, tailored to their unique perspectives.

Looking Ahead: AI in 2025 and Beyond

In 2025 and beyond, AI adoption in charitable planning will continue accelerating. Here’s what to expect:

• Wider Adoption: Smaller nonprofits will embrace AI tools, leveling the playing field with larger organizations.
• Greater Accuracy: Contained systems like Frank™ and Max™ will aid in setting trust and reliability standards.
• Deeper Integration: AI will connect donor data, financial tools, and communication platforms, enabling seamless workflows for advisors and nonprofits.

Conclusion: The Human-AI Partnership

AI is not here to replace advisors but to enhance their expertise. By combining generative AI’s creativity with agentic AI’s proactive capabilities, advisors can focus on what they do best: building relationships, providing measured advice, understanding donor motivations, and crafting meaningful legacies.

About the Author

Paul Caspersen
President and Founder of Planned Giving Interactive & Vice President, Charitable Solutions, LLC

Paul is the Founder of Planned Giving Interactive (PGI), a charitable planning software and consulting firm. He also serves as Vice President at Charitable Solutions, LLC, where he acts as a technical advisor to donors, charities, and financial professionals on advanced charitable planning strategies, particular with non-cash assets and charitable trusts.

The opinions expressed in this article are solely those of the author and do not reflect the views or endorsements of the American Heart Association (AHA). The AHA does not endorse or assume responsibility for any information or opinions presented in this article.