ChabadLabs AI FOR SHLICHUS

Letter Writing & Communications

Fundraising letters, thank-yous, and tone-matching prompts.

On this page

Drafting letters, emails, and short writing in a voice that sounds human, and ideally like you. A foundational use case from the chat's first weeks.

What the group settled on

Use caseModel
Pastoral / emotional / "knowing your baalei batim"Claude
Personality / fun / casual toneGrok
Default workhorseChatGPT
Style-matching past work (uploaded examples)Claude with examples in the chat, a Project, or a Custom GPT

"Claude is better in my experience than ChatGPT. Provide a good outline of what you want the letter to say."

"I find that Grok writes with more personality and a more genuine tone than ChatGPT."

The three workable patterns

1. Upload examples; let it copy your voice

A eulogy workflow:

  • Upload 20+ past eulogies you've written.
  • Add a system message: "Copy this style for future writing."
  • When a new eulogy is needed, take notes with the family, paste them into the same chat, and get a draft that matches your prior style (similar openings, similar closings).

This generalizes to thank-you letters, sponsor letters, condolence notes, and press releases.

2. System-prompt rules

The most-shared writing prompt in the chat, an anti-AI style sheet. The key constraints:

  • No em-dashes ever (use commas, semicolons, or two sentences).
  • No "leverage", "synergy", "tapestry", "delve", "in conclusion".
  • Active voice. Short paragraphs. Vary sentence length.
  • A Flesch reading score of 80 or higher.
  • Avoid adverbs. No clichés. Plain English.
  • Acknowledge with "Got it" and then respond to the actual request.

See the full prompt in Master Prompts.

3. Dia / writing-aware browser

Dia has a built-in AI assistant where you pre-load your writing style and sample authors once, and then everything you write gets ghostwritten in that voice without re-prompting each time.

Specific letter use cases

Fundraising letters at a 6th-grade reading level

The Jeff Brooks technique, adapted:

  1. Write your own draft.
  2. Ask AI: "Rewrite this at a 6th-grade reading level while keeping my voice and main points."
  3. The result is more accessible and historically gets higher response rates.

Press releases

Generating press releases plus media-list customization is a chat specialty. The pattern: write one well-targeted release; generate ten variations per outlet; check before sending.

Grant proposals

Paste the grant questions into AI with your Chabad House context; AI fills out the answers. Then you edit. It saves hours.

Eulogies / hespedim

The pattern above. Also use AI to research the deceased, the names, dates, family members, and public mentions, before the family meeting.

Condolence / yahrtzeit notes

Use the recipient's name and one specific memory; AI writes the connective tissue. Don't trust AI to find the memory, that is your job.

"Sounds too AI": fighting the tells

Common AI tells in letters:

  • Em-dashes everywhere. Strip them.
  • "In today's world, ..." / "In conclusion, ..." Cut these.
  • Triadic sentences. "Faster, smarter, kinder." Three is the AI default.
  • Repeated framings. "Not just X, but Y." "It's not about A, it's about B."
  • Verb-heavy openings. "Imagine." "Picture." "Consider."

The 2026-04 TechCrunch article "AI Writing: It's not just this, it's that" catalogs the patterns at length.

Honest-feedback prompts

When the AI is sycophantic ("That's a great idea! You're brilliant!"):

"Be direct and brutally honest. Stress-test my ideas hard. If something is weak, say so plainly and explain why. Think from first principles, use logic over sentiment, and push until the argument is solid."

"Recently I asked GPT to criticize my output and be 'merciless' about it. It worked."

"After AI response: 'Rate your response out of 10.' If not satisfied, give your own rating, e.g., 'I'd rate that a 6/10.' AI recalibrates its understanding of what you need."

Pre-response clarification

"Ask me clarifying questions to make sure we're on the same page before responding or doing a task."

A small prompt addition that prevents misinterpretations on complicated writing tasks.

ZeroGPT check

"Always paste your text into zerogpt.com or similar before posting to see if it's too much AI."

Last updated May 2026 · Maintained by Hermes AI Agent