Many association executives sit on decades’ worth of strategic intelligence — and barely use it.

IRS Form 990 and audited financial statements are public, structured, and richly detailed, yet most organizations treat them as compliance artifacts rather than decision-making tools. As leadership teams navigate digital transformation, AI adoption, and shifting member expectations, they need insight that is role-aware, fast, and strategically aligned.

Generative AI has the potential to fill that gap — but only when paired with intentional prompt and context design. This article shows how a structured prompting system, applied to Form 990 and audit data, can generate executive-ready briefings tailored to roles like CIO, CFO, or board chair. Through persona-aware prompts, structured prompt design, and cross-model testing, associations can turn overlooked data into an asset for strategic onboarding, planning, and governance.

We’ll explore a hybrid approach — combining prompt engineering¹ and context engineering²— to create structured, persona-driven briefings.

You’ll see the practical utility of prompt-system architecture in nonprofit strategic contexts and how this repeatable model for data reuse supports digital transformation, transparency, and institutional knowledge continuity. A cautionary note, though: Associations always need to exercise discretion when using ChatGPT or any other AI model since data used with these tools can be resourced in the future by other users³.

The Humble 990 – A Missed Strategic Asset

IRS Form 990 is often seen as a compliance requirement — an annual box to check for regulators and watchdog groups. But beneath its columns and checkboxes lies a longitudinal record of an organization’s operational heartbeat: where money comes from, how it’s spent, what resources are allocated to mission-critical activities, and how priorities shift over time.

For many association leaders, the 990 lives in the finance department, surfacing only during audit season or donor due diligence. It’s a lesser-used asset for strategic planning, executive onboarding, or internal performance alignment.

This mindset leaves high-value insight untapped as a leadership resource, especially for new C-suite leaders who are asked to navigate shifting program portfolios, digital transformation, and cross-functional decision-making without a reliable map of how the organization operates.

That’s where AI comes in. When paired with structured prompting techniques, tools like ChatGPT or Gemini can ingest a decade’s worth of 990s and surface actionable intelligence. They can track the evolution of unrestricted funding, flag cost drift in specific programs, detect patterns in staffing or outsourcing, and correlate investment gains with risk exposure. In short: AI can turn a static financial disclosure into a living map of organizational behavior. Flagging, for instance, a steady rise in program costs despite stagnant funding.

This transformation — from passive compliance form to strategic instrument — starts with asking better questions. What if your next CIO briefing began not with a mission statement, but with an AI-synthesized pattern report drawn directly from your last 10 Form 990s?

Structured Prompting as a Lens

Turning raw data into strategic insight demands intentional structure. That’s where prompt and context engineering enter the picture.

At the core of our approach is persona-based prompting, a technique that tailors the AI’s response to the needs, language, and goals of a specific stakeholder. For this project, we began with a defined audience: the incoming chief information officer at a scholarly society. We asked ourselves, “What would a CIO need to know about this organization in the first six months?” and shaped the prompt and context accordingly.

The result is a role-aware, executive-aligned prompt that synthesizes IRS Form 990s and other public documents into a structured, onboarding-ready briefing. In a nonprofit environment where strategic bandwidth is thin and onboarding timelines are compressed, prompts like this offer a replicable way to turn compliance-driven records into clarity-driven intelligence.

This type of prompt is more than a question — it’s a structured lens. It guides the AI to focus on what matters to the CIO, aligning output with key themes of nonprofit digital transformation: data visibility, tech modernization, operational alignment, and governance transparency.

It also represents a powerful hub-and-spoke model for repurposing public data. At the hub: IRS Form 990s and audited financials — data-rich but underleveraged. Use of this modular model means every leadership role can receive data in its most useful format, no new data required. Our potential spokes might include:

• CIO strategic briefing: infrastructure, data strategy, and modernization priorities
• Board oversight dashboard: governance and fiduciary alignment
• Enterprise risk summary – cybersecurity, regulatory, and data exposure
• Interdepartmental map – cross-functional gaps and synergies

Each output uses the same data source but different persona prompts, decomposition steps, or framing techniques — what we’ve termed prompt strategy layers. These layers include persona targeting (who the AI is answering to), structured decomposition (how the request is broken into components), and response formatting (how the output is shaped for readability and use).

By combining multiple techniques, we created prompts that were not only informative, but strategically aligned and reproducible across models.

The Prompt – Development and Testing

In exploring whether we could extract meaningful strategic insight from IRS forms, we ultimately developed two prompts, each suited to a specific audience:

• “SP_PROMPT” is aimed at senior financial leadership. It extracts and analyzes nonprofit financial data to produce concise, one-page executive briefings. It emphasizes funding trends, cost efficiency, and risk, using IRS Forms 990 and 990-T. The tone is factual, data-driven, and optimized for boardroom clarity.
• “TM_PROMPT” is designed for a newly arrived CIO and generates strategic onboarding briefings based on public organizational documents. It focuses on digital transformation, IT modernization, data governance, and platform strategy. The output is structured, high-level, and aligned with executive technology leadership priorities.

The differences between these outputs stem directly from how each prompt is structured and framed. SP_PROMPT is tightly formatted and directive-driven, making it well-suited for fast, precise financial analysis. TM_PROMPT, on the other hand, takes a more flexible, narrative approach that supports strategic thinking from a CIO’s perspective. Together, they show how prompt design can be tailored to serve very different roles within a nonprofit.

Conclusion: Toward Prompt-Driven Strategy

Prompt engineering isn’t just a technical skill — it’s a strategic one. As this project shows, the ability to structure AI output with clarity and role-awareness can transform static disclosures into dynamic decision tools. For association leaders facing time constraints, turnover, and digital transformation, prompt-driven insight offers a scalable path to continuity, accountability, and better decisions.

To review the full prompt sets (SP_PROMPT and TM_PROMPT) and test data, contact the authors.