Workbench guide
How to Write Better Cold Emails With Research and AI
Research a business properly, write a first message that is actually useful, and follow up without being a pest. With prompts, examples, and the legal basics on consent and opt-outs.

In this piece
Why it matters
Most cold emails are ignored because they could have been sent to anyone. Ten minutes of real research is what makes yours worth reading.
A good cold email is short, specific, and useful to the person who gets it, even if they never reply. This guide shows how to research one business, write one message, and follow up once or twice. It also covers the rules you must follow.
It will not tell you how to send thousands of emails. That approach hurts your sender reputation and annoys people, and it is not what this method is for.
What you need
| Tool | Cost | What it is for |
|---|---|---|
| The business's own website and public pages | Free | Understanding what they do and what they care about |
| An AI assistant such as Claude or ChatGPT | Free plans available, with limits | Summarizing research and drafting, never sending |
| Your normal email account on your own domain | Varies | Sending one message at a time |
| A simple spreadsheet | Free | Tracking who you wrote to, when, and who asked you to stop |
Step-by-step
Step 1: Choose prospects responsibly
Pick a small number of businesses where you have a real reason to write. A good reason sounds like "they just launched a booking page and it is slow on phones," not "they are in my target industry."
- Use a business contact address the company publishes, or the address of the person whose role matches your message.
- Do not buy email lists, scrape personal addresses, or guess addresses by pattern.
- Keep a record of where you found each address.
Step 2: Understand the business
Spend ten minutes on their own website before you write a word. Then use AI to organize what you found, not to invent what you did not.
Below are notes and text I copied from [BUSINESS NAME]'s own website and public pages. Using ONLY this material, tell me:
1. What they sell, and to whom, in two sentences.
2. Anything that looks recent: a launch, a new location, a hiring post, a changed page.
3. One problem they might have that relates to [WHAT I OFFER], and the exact line in my notes that suggests it.
4. What you could not tell from this material.
If something is not in my notes, say "not in the notes." Do not guess, and do not add facts from elsewhere.
MY NOTES
[PASTE WHAT YOU COPIED]
The fourth question matters most. It shows you where you would be guessing.
Step 3: Write a useful first message
A useful first message does four things: says who you are, shows you looked at their business, offers one specific thing, and makes saying no easy.
Write a first email from me to [NAME, ROLE] at [BUSINESS].
About me: [ONE SENTENCE ON WHO I AM AND WHAT I DO].
The one specific observation: [FROM YOUR RESEARCH, WITH WHERE YOU SAW IT].
The one thing I can offer: [A CONCRETE, SMALL OFFER, FOR EXAMPLE: a short list of three fixes, free].
Rules:
- Under 120 words. Plain text, no images, no tracking links.
- A subject line that describes the email honestly. No "Re:" or "Quick question" tricks.
- Mention only facts from my observation. Do not invent compliments, numbers or results.
- One clear question at the end that is easy to answer yes or no.
- A last line saying they can reply "no thanks" and I will not write again.
- Simple American English. No hype words.
Here is an example of the kind of message this produces. The business is made up.
Subject: Your new booking page on phones
Hi Maya,
I'm Sam, a web developer in Austin. I tried the new booking page on Riverside Pilates from my phone, and the date picker took about eight seconds to appear on a normal connection.
I wrote down three changes that would likely speed it up. They are free, with no strings attached. Would you like me to send them over?
If this isn't useful, just reply "no thanks" and I won't write again.
Sam Lee, Lee Web Studio, 120 Example St, Austin, TX
Step 4: Check personalization before you send
Read the draft out loud and check every claim against your notes. AI drafts often add a friendly detail that is not true, such as praising a project the business never did. Delete anything you cannot point to.
Step 5: Follow up, once or twice
If there is no reply after about a week, one short follow-up is reasonable. After a second follow-up with no answer, stop.
Write a follow-up to my email below. Under 60 words. Do not repeat the whole pitch, do not guilt them, and do not pretend they replied. Offer the same one thing, and repeat that they can reply "no thanks" and I will stop.
MY FIRST EMAIL
[PASTE IT]
Rules on consent, opt-outs and sending
This is a summary, not legal advice. The rules depend on where you and the recipient are.
United States. The [1] applies to commercial email, including business to business. Among other things, it requires accurate sender details, a subject line that is not deceptive, a valid physical postal address, a clear way to opt out, and honoring opt-outs within 10 business days. The FTC says each violating email can carry a penalty of up to $53,088.
Gmail and other inboxes. Google's [2] require every sender to authenticate their domain with SPF or DKIM and keep spam reports low. Senders of more than 5,000 messages a day to Gmail need SPF, DKIM and DMARC, plus one-click unsubscribe for marketing email.
UK, EU and Canada. These places have stricter consent rules for some types of recipients. In the UK, the [3] treats sole traders differently from companies. Canada's anti-spam law generally requires consent before you send, as the [4]. Check before you write to people there.
Where AI helps, and where a person must decide
| AI helps with | A person must decide |
|---|---|
| Summarizing what you collected | Whether you have a real reason to write |
| A first draft in plain language | Whether every claim is true |
| A shorter follow-up | Whether to follow up at all |
| Spotting hype words and long sentences | Sending, one message at a time |
Common mistakes
- Writing about yourself first. Start with their business, not your résumé.
- Fake personalization. "I love your work!" with nothing specific reads as a template.
- Asking for a 30-minute call. Offer something small and useful instead.
- Too many follow-ups. Two is plenty.
- No easy way out. Always tell people how to stop hearing from you, and keep a list of those who asked.
- Sending from a brand-new domain in bulk. This is how sender reputations get damaged.
Frequently asked questions
Can I use ChatGPT or Claude to write cold emails?
Yes, for research summaries and first drafts. Check every claim against your own notes, and send each message yourself. Never let a tool send emails for you.
How long should a cold email be?
Short. Under 120 words for a first message, and under 60 for a follow-up. If it does not fit on a phone screen, it is too long.
How many follow-ups should I send?
One or two, about a week apart. After that, stop.
Is cold email legal?
In the United States, commercial email is allowed if you follow the CAN-SPAM rules: honest sender details and subject line, a postal address, and a working way to opt out. The UK, EU and Canada have stricter consent rules. This is not legal advice, so check the rules where your recipients are.
Tools and resources
- CAN-SPAM Act compliance guide The FTC's plain-language rules for commercial email in the United States. ftc.gov
- Google email sender guidelines What Gmail expects from anyone sending email to its users. support.google.com
Sources
- CAN-SPAM Act: A Compliance Guide for Business, Federal Trade Commission (ftc.gov)
- Email sender guidelines, Google Workspace Admin Help (support.google.com)
- Business-to-business marketing, Information Commissioner's Office (ico.org.uk)
- Frequently Asked Questions about Canada's Anti-Spam Legislation, CRTC (crtc.gc.ca)
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