Making AI Approachable with a Custom Newsletter Assistant—GIPNA

AI Tools & Training • Product and Service Design • Content and Instructional Design

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The Greater Independence Park Neighborhood Association (GIPNA) is a 501(c)(3) nonprofit focused on improving quality of life in Chicago’s Independence Park neighborhood through community engagement and neighborhood enrichment. The association serves residents across the 30th and 45th Wards.

GIPNA publishes a bimonthly print newsletter, the Independence Park Community Voice (nicknamed The Voice), which reaches 750 households and businesses per issue—about 4,500 printed copies annually. The newsletter shares local updates, event promotions, civic information, and neighbor-submitted stories, and is also archived digitally at gipna.org/newsletter.

The challenge.

Producing a high-quality community newsletter with a team of over 20 rotating volunteers requires both consistency and speed. Contributors bring a wide range of writing styles, experience levels, and comfort with deadlines. When I became the Editor-in-Chief in 2023, I realized that team members often spend significant time rewriting for tone, fixing grammar, and handling last-minute content just before layout. Proofreading and translations introduce additional delays. These efforts, while important, take time away from broader engagement and storytelling goals. As a result, coverage can feel uneven and time-sensitive events may be missed. Without new tools to support the team, we risk burnout, slower production, and a loss of participation over time.

The approach.

Select the image above to see News Laddy in action (you’ll just need a free ChatGPT account, if you don’t have one already).

I created a custom GPT—nicknamed the News Laddy—and trained it on past issues of The Voice, style guidelines, content categories, and publishing schedules. I also supported the editorial team and GIPNA board by leading training, gathering feedback, and iterating the tool for daily use. To do this I:

1. Mapped the newsletter workflow to identify where the greatest time and energy were being spent

2. Built a custom GPT using OpenAI’s tools, trained newsletter archives and tone/style prompts

3. Created role-based scenarios (e.g., “help me rewrite this article,” “suggest a title,” “translate this calendar”) to guide use

4. Extensively tested and refined the GPT configuration

5. Provided live training sessions and written guides for editors and contributors

6. Integrated the tool into the editing and planning process during active production cycles

7. Iterated based on real-world use, including formatting workarounds and fine-tuning prompt behavior

The results.

The News Laddy has become a trusted assistant for newsletter production, helping contributors generate drafts, editors clean up tone and grammar, and planners quickly generate ideas or adapt to late-breaking news. It's also encouraged new participants to contribute content by lowering the barrier to entry.

In the first few issues using the News Laddy:

• First-time contributors submitted full-length features with GPT assistance

• Detailed event write-ups were print-ready within 24 hours of happening, something rarely possible before

• Calendar translation turnaround dropped from several days to less than 15 minutes

Part of my role as Editor-in-Chief is supporting and growing our team of staff writers and special contributors. Since taking over this role at the end of 2023 the number of writers has increased substantially, with an increase of over 42% overall in 2024, and an increase of over 70% in special contributors (those who contribute 1-3 articles a year). This is largely due to my improvement of our process and the introduction of AI tools and training.