Draft Cold DMs for Freelance Outreach with ChatGPT or Claude
Job to be done: Draft client communication for awkward freelance moments
🇳🇬 Ways to use this in Nigeria
Ideas to get you started, adapt to your situation.
- Entrepreneur
Draft a personalized LinkedIn DM to a potential investor referencing their recent company announcement, asking a genuine question to start a conversation.
- Student
Create a casual Instagram DM to a potential collaborator for a school project, referencing their recent art post and asking about their process.
- 9-5 employee
Draft a concise LinkedIn message to a potential client, referencing their company's new product launch and asking a specific question about it.
What you’ll get
Ready-to-send messages for initial client outreach, designed to open a conversation without immediately pitching your services. This approach uses AI to draft professional, concise, and human-sounding communication, saving time and reducing stress for freelancers.
Tools you need
- ChatGPT (freemium): An AI chatbot for generating text and conversations.
- Claude (freemium): Another AI chatbot known for its conversational abilities and longer context windows.
Steps
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Open your AI chat tool: Go to either ChatGPT (chatgpt.com) or Claude (claude.ai) in your web browser or mobile app. You will need to sign in or create a free account.
You should see the chat interface ready for you to type a message.
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Draft a cold DM opener: Copy the prompt below. Replace the bracketed placeholders
[PLATFORM],[PROSPECT_NAME],[OBSERVATION], and[YOUR_FIELD]with your specific details. Then, paste the complete prompt into the chat tool and send it.You are a freelancer writing a first-touch DM to a potential client on [PLATFORM: LinkedIn/Instagram]. You are NOT pitching yet — only opening a conversation. Inputs: - Prospect's name: [PROSPECT_NAME] - Something specific and real you noticed about them (a post, their business, a recent launch): [OBSERVATION] - Your area of work (one line, no pitch): [YOUR_FIELD] Write a DM under 40 words that: 1. References [OBSERVATION] specifically — not a generic compliment. 2. Asks ONE genuine question related to [OBSERVATION]. 3. Does NOT mention your services, price, or availability. 4. Sounds like a real person typing on their phone, not a copywriter. Output the DM only.You should get a short, personal message under 40 words, ready to send to a potential client without sounding like a sales pitch. The author mentioned sharing three prompts, but only this one was included in the provided excerpt.
Original source
This workflow is adapted from a Reddit post by user /u/lucky3pointer, shared on August 2, 2026. The author developed these prompts as part of ‘Cleardesk Prompts’ to help freelancers with tricky client communications.
Notes & variations
- Common mistake: Not being specific enough when filling in the bracketed information. Generic inputs lead to generic outputs. Ensure
[OBSERVATION]is a real, unique detail about the prospect. - Tip for better results: Experiment with the tone. If the output sounds too formal, you can add a line to the prompt like “Make it sound more casual” or “Use a friendly tone.” Always review the AI’s output to ensure it matches your personal style before sending.
- Free-tier viability: Both ChatGPT and Claude offer robust free tiers that are perfectly capable of handling this text-based workflow without needing paid upgrades.