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Writing with AI

📖 Lesson content

What you'll learn

Estimated time: 50 minutes

By the end of this lesson you'll be able to:

  • Apply Description skills to craft clear, context-rich prompts that guide AI to create or improve written materials aligned with your nonprofit's mission and audience needs
  • Apply Discernment skills to evaluate AI-generated written materials for accuracy, appropriateness, and alignment with your organizational values and communication standards

Writing with AI

(7 minutes)

This video demonstrates the Description-Discernment loop applied to writing, with a focus on maintaining authenticity and human connection. You'll follow James, who runs a small environmental justice organization, as he uses AI to write an emergency grant proposal under a 48-hour deadline. The video shows how to provide rich context through uploaded documents, guide AI's approach with specific instructions, and iterate through discernment to create a proposal he can stand behind.

Key takeaways

  • Upload past successful work to help AI understand your organization's voice and approach—this saves time and improves authenticity
  • Inject the details AI can't know: your track record, partnerships, staff expertise, and actual community relationships
  • Be specific in your revisions: Instead of "make this more compelling," say "add these specific details about our community relationships"
  • Let your expertise guide every revision: AI helps you write faster, but you're shaping the substance
  • Build a cognitive environment: The back-and-forth between human and AI helps align the tool to your specific needs over time
  • Own the final result: When you submit work created with AI assistance, you should be able to stand behind every word because you applied discernment throughout

Exercise 1: Grant proposal

This exercise helps you practice using Description and Discernment to create high-stakes fundraising content that authentically represents your organization.

Part I: Self-reflection

Select a program or initiative you need funding for. Craft a writing prompt that includes:

  • The grant opportunity and what the funder cares about
  • Your program's key details (who, what, where, outcomes)
  • Your organization's voice and values
  • Specific requirements (word count, required elements, tone)
  • What makes your approach unique or effective

Part II: Collaboration

Share your prompt with AI and review the draft. Apply Discernment:

  • Verify all data points and outcomes claimed are accurate
  • Check if the language reflects your organization's actual voice or sounds generic
  • Identify any deficit-based framing or problematic language about beneficiaries
  • Assess whether it addresses the funder's priorities or just describes your program
  • Note what's missing that only you know about your work

Part III: Reflection

  • What context did you initially forget to include that would have improved the draft?
  • What would you revise in your prompt to better capture your organization's unique approach?
  • Which parts of the AI draft are usable versus which need complete rewriting?

Stretch goal: Iterate on your prompt with specific feedback about tone or framing issues you identified, then compare the two versions to see how description improvements affected output quality.

Exercise 2: Social media posts

This exercise applies Description and Discernment to content that requires capturing your organization's authentic voice for public audiences.

Part I: Self-reflection

Choose your content goal:

  • Highlight a program impact or success story
  • Promote an upcoming event or campaign
  • Share educational content related to your mission
  • Thank donors or volunteers

Craft a writing prompt that includes:

  • Platform and format (Instagram carousel, LinkedIn post, Facebook story, etc.)
  • Your audience and what motivates them
  • Key message and call-to-action
  • Your organization's social media voice (professional, playful, activist, etc.)
  • Any visual elements needed (infographic data, quote graphic, photo description)
  • Constraints (character limits, hashtag strategy, accessibility requirements)

Part II: Collaboration

Share your prompt with AI and review the content. Apply Discernment:

  • Check if the tone matches how your organization actually communicates
  • Verify any statistics or claims are accurate and current
  • Assess if language respects the dignity of people you serve
  • Evaluate visual suggestions for accessibility (alt text, color contrast if applicable)
  • Consider whether this content would resonate with your actual followers or feels generic

Part III: Reflection

  • Did your prompt capture what makes your organization's social media voice distinctive?
  • What elements of the draft would you keep versus rewrite completely?
  • If you requested a visualization, does it tell the right story for your audience?

Stretch goal: Ask AI to create 3 variations for different platforms (Instagram, LinkedIn, Twitter/X) and evaluate how well it adapted the core message to each platform's audience and norms.

Lesson reflection

  • How did uploading past work or providing detailed context change the quality of AI's writing output?
  • What strategies will you use to maintain your organization's authentic voice when writing with AI?

What's next

In the next lesson, we'll explore AI Privacy in an attempt to better understand what happens to the data you share with AI.

Feedback

As you progress through the course, we'd love to hear from you about how you are using concepts from the course in your work and any feedback you may have. Share your feedback here.

🎬 Video transcript

Source video: OQzANXIckWo

📜 Click to expand transcript (cleaned + AI-translated)

The Importance of Human Connection in Nonprofit Writing

Almost by definition, human issues are the heart of most nonprofits' missions, whether it's directly supporting people in need, protecting the environments they live in, or performing research or advocacy on their behalf. So naturally, when writing for a nonprofit organization, human connection is essential.

To maintain this connection while leveraging technology, we apply the Description Discernment Loop to writing. This framework allows you to work with AI in a way that supports authenticity and saves time. The Description Discernment Loop is how you work with AI day-to-day: you describe what you want, evaluate what you get, then refine your next request. For writing, this means drafting and then working section by section to produce something of high quality.

Case Study: Emergency Grant Writing

Grant writing is one of the biggest challenges nonprofit leaders face, especially under tight deadlines. You need to move fast, represent your organization well, and demonstrate a genuine capacity to use donor funds effectively.

Consider this hypothetical situation: A severe ice storm just hit Detroit, taking down over 15,000 trees. The damage is worst in lower-income neighborhoods with less tree canopy coverage. Detroit's Office of Sustainability has announced emergency funding: $50,000 grants for rapid tree replacement and debris management. Proposals are due in 48 hours.

James runs the Green Detroit Coalition, a small environmental justice organization. While they have experience in tree planting, they have never handled an emergency response at this scale. James needs to write a compelling proposal quickly so he can return to the field.

Crafting the Initial Prompt

James starts his initial prompt by focusing on three key areas:

  • Product Description: He is clear about the output—four specific sections, 1,000 words total, covering capacity, approach, timeline, and environmental justice.
  • Process: James guides how the AI should approach the task. He provides examples, such as past grant proposals and brand elements like his mission one-pager. This allows the AI to learn the organization's voice, tone, and strengths before it begins writing.
  • Performance Considerations: James specifies that the result must be confident yet community-focused, and data-driven while centering residents' perspectives. He explicitly defines environmental justice for his coalition as power-sharing and community decision-making, not just planting trees.

Providing Context through Documentation

Giving AI examples of past work and style through uploaded documents is essential for information-rich, high-quality writing. As you build a collaborative environment, you can use tools like Claude’s projects, connectors, or styles to provide necessary context.

The Discernment Phase: Reviewing AI Output

Once the AI generates a first draft, the discernment phase begins. This involves reviewing the output for gaps in product, process, and performance. Key questions to ask during this review include:

  • Do the specific grant details look correct?
  • Did the AI consider the voice, tone, and structure from the uploaded context?
  • Does it align with the organizational values outlined in the mission document?
  • Does this reflect actual capacity or make false assumptions?

In James's case, he might notice the "organizational capacity" section undersells their existing relationships, or the "timeline" fails to account for community input—a process error.

Building a Cognitive Environment

The loop continues as James requests revisions and gives further direction. This back-and-forth builds a cognitive environment, aligning the AI to specific organizational needs. Eventually, after several iterations, the human lead takes over to add the final touches. The AI handles the first draft, but the final substance remains the responsibility of the human expert.

Strategies for Effective AI Collaboration

To make this process effective, consider the following strategies:

  • Upload past successful proposals: This helps the AI understand your organization's voice and approach, improving authenticity.
  • Inject unique details: Provide the information AI cannot know, such as your specific track record, partnerships, staff expertise, and community relationships.
  • Be specific in revisions: Instead of saying "make this compelling," say "add these specific details about our community relationships."
  • Let expertise guide every revision: AI helps you write faster, but you are shaping the substance.

By applying discernment throughout the process—verifying claims and ensuring authenticity—you can take full ownership of the final product, ensuring it truly supports the community you serve.

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