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Letter Writing & Communications

Thank-you notes, appeals, eulogies, press releases and emails with AI: give it your own past writing, strip the AI tells, check every fact, and send only after you read it.

On this page

Drafting letters was one of the first things shluchim used AI for, and it is still one of the most common. The draft is fast. Making it sound like the shliach, and not like a chatbot, is the work.

Which model

Members' preferences shifted over the year, so treat this as the group's experience, not a ranking:

  • Claude: preferred by many for pastoral letters, condolence notes and grant narratives (2025 and 2026).
  • ChatGPT: by July 2026 a group admin said ChatGPT "has caught up majorly" and recommended it to beginners. One member finds it best for letters because it remembers his history and style across chats.
  • Grok: some members in 2025 liked its more casual, personal tone.

Any of them works if you give it good material. The difference between a flat letter and a good one is usually what you paste in.

Make it write like you

Upload your own writing

A eulogy method from 2025 that generalizes to everything:

  1. Upload 20 or so of your past eulogies (or thank-you letters, or sponsor letters).
  2. Tell it: "Study my style and use it for future writing."
  3. After meeting the family, paste your notes into the same chat and ask for a draft in your style.

A Claude Project, a custom GPT or a Gemini Gem keeps those samples and instructions for every future chat. For social media posts after an event, members did the same with a few sample posts.

Give it rules

The group's most-shared writing prompt is an anti-AI style sheet. Its main rules:

  • No em dashes.
  • No "leverage," "synergy," "tapestry," "delve," "in conclusion."
  • Active voice, short paragraphs, mixed sentence lengths.
  • Plain words; aim for an easy reading score.

The full prompt is in Master Prompts, and the short how-to is the guide How do I get AI writing to sound like me.

The tells to strip out

  • Em dashes everywhere.
  • "Not just X, but Y" and "It's not about A, it's about B."
  • Lists of three: "faster, smarter, kinder."
  • Openers like "In today's world" and closers like "In conclusion."
  • Every paragraph the same length.

In August 2026 a vendor's AI-personalized emails to shluchim, each with a paragraph about the recipient's family, drew replies like "it's obviously AI" and "turns me off." People notice.

Online AI detectors are not a reliable check. Independent tests, including a 2023 Stanford study, found they often flag human writing as AI, especially from people writing in a second language. Read the letter aloud instead.

Specific jobs

Fundraising appeals

Write the draft or dictate notes, then ask for a version at about a sixth grade reading level that keeps your voice and every fact. Fundraising writer Jeff Brooks recommends a fourth to sixth grade level for appeals. More in Fundraising.

Grant proposals

Paste the funder's questions and your program details, and answer one question at a time. Models miscount words; write "hard cap of 300 words" and check the count yourself (July 2026).

Eulogies and condolence notes

Use the method above. AI can also help you organize names, dates and family members before the family meeting. The one specific memory that makes the note personal has to come from you.

Press releases

Write one well-aimed release, then ask for versions for each outlet. Check every name and date before sending.

Speeches

Ask AI to tighten a talk to under five minutes, or to mark pauses and emphasis for delivery (January 2026). For a sermon, a member split it into two steps in September 2026: transcribe, then ask for feedback on clarity.

Honest feedback

When the AI just praises your draft:

"Be direct and brutally honest. Stress-test my ideas hard. If something is weak, say so plainly and explain why."

Two other habits from the group: ask it to rate its own answer out of ten and say what would make it a ten, and give your own rating ("that's a 6 out of 10") so it knows what you want. Before a complicated task, add: "Ask me clarifying questions before you start."

Email: draft, do not send

Claude and ChatGPT can both connect to Gmail. The group's rule (October 2026): let the AI create drafts, then read and send them yourself. A member who asked ChatGPT to design and send a test email through ChabadOne Communicator saw it go out in under a minute without waiting for approval. Say "show me the draft, do not send." See Privacy & Data.

Last updated October 2026 · Maintained by ChabadLabs AI Agent