Draft Follow-Up Emails for Silent Clients with ChatGPT or Claude

What you’ll get

Two ready-to-send follow-up emails for clients or prospects who have gone quiet after a proposal or pitch. This approach helps you avoid common, ignored phrases like “just following up” and instead adds new value, making it easier for the recipient to reply.

Tools you need

• ChatGPT (freemium): An AI chatbot that can generate human-like text based on your prompts.
• Claude (freemium): Another AI chatbot, similar to ChatGPT, known for its ability to handle longer texts and nuanced conversations.

Steps

1. Choose your AI tool: Open either ChatGPT or Claude in your web browser or mobile app. You can use the free versions of both.

   • What you should see: The chat interface ready for you to type a message.

2. Copy the follow-up prompt: This prompt is for when a prospect hasn’t replied after you sent a proposal or pitch. Copy the entire text below:

   You are a freelancer following up on [MESSAGE_TYPE: a proposal/an email/a DM] sent [TIME_SINCE] ago that got no reply. Inputs: - Original message topic (one line): [ORIGINAL_TOPIC] - Recipient's name: [RECIPIENT_NAME] Write a follow-up under 50 words that: 1. Does NOT say "just following up" or "checking in" (banned phrases — overused and ignored). 2. Adds ONE new piece of value or information not in the original message (an idea, a resource, a short insight related to [ORIGINAL_TOPIC]). 3. Makes replying effortless — end with a question answerable in one word. 4. Assumes positive intent — no guilt-tripping about the silence. Output the follow-up only.

   • What you should see: The prompt copied to your clipboard.

3. Paste and fill in the details: Paste the prompt into the chat window of your chosen AI tool. Then, carefully replace the bracketed placeholders [MESSAGE_TYPE], [TIME_SINCE], [ORIGINAL_TOPIC], and [RECIPIENT_NAME] with your specific information.

   • For [MESSAGE_TYPE], choose one: a proposal, an email, or a DM.
   • For [TIME_SINCE], state how long ago you sent the message, e.g., five days, a week, two weeks.
   • For [ORIGINAL_TOPIC], briefly describe what your original message was about, e.g., "website copy refresh for the product launch".
   • For [RECIPIENT_NAME], enter the person’s first name, e.g., "Maya".
   • What you should see: The prompt with all the bracketed parts filled in, ready to send.

4. Send the prompt and review the email: Press Enter or click the send button. The AI will generate a short follow-up email based on your inputs and the rules in the prompt.

   • What you should see: A concise email, under 50 words, that avoids “just following up,” adds a new piece of value, and ends with a simple question. For example, if your inputs were “proposal,” “five days,” “website copy refresh for the product launch,” and “Maya,” you might see something like:

     Hi Maya,
     
     Hope this finds you well. Just saw a great article on conversion-focused headlines that made me think of your product launch. Could that be helpful?

Original source

This workflow comes from a Reddit post by user /u/lucky3pointer, who shared a prompt template from their “Cleardesk Prompts” pack. The author tested these prompts in ChatGPT and Claude to ensure they work well for real-world freelance client communication.

Notes & variations

• Free-tier viability: Both ChatGPT and Claude offer robust free tiers that are perfectly sufficient for this task. You won’t need to pay for a subscription to generate these emails.
• Common mistake: Don’t forget to fill in all the bracketed placeholders in the prompt. If you leave them blank, the AI might generate a generic response or ask you for more information.
• Tip for better results: If the AI’s suggested “new piece of value” isn’t quite right, you can try running the prompt again or slightly adjusting your [ORIGINAL_TOPIC] to give the AI a clearer direction. For example, instead of just “website copy refresh,” you could say “website copy refresh for a new SaaS product launch targeting small businesses.” This helps the AI generate more relevant ideas.
• Missing prompt: The author mentioned a second scenario for a client who said “let me think about it” and vanished, but the specific prompt for that situation was not included in the excerpt. This entry only covers the “no reply after a proposal or pitch” scenario.