I Used to Hate AI-Generated Emails

Early on, I tried using ChatGPT to write cold emails. As a web developer who didn't know how to sell my services, I thought AI could help. I pasted in a URL, asked it to write a personalized outreach email, and got this masterpiece:

"Dear Valued Business Owner,

I hope this email finds you well. I was thoroughly impressed by your website and believe there are tremendous opportunities to enhance your digital presence and maximize your online potential...

Looking forward to synergizing with you!"

Yeah. "Synergizing." That's a real word that real humans definitely use in casual emails.

I sent it anyway (don't judge me, I was curious). Zero responses. Not even a spam folder confirmation.

The Problem With Most AI Email Tools

Here's what I learned: AI isn't the problem. How people use AI is the problem.

Most people treat AI like a magic button. Paste URL, click generate, copy-paste the output, send to 50 people. Then they wonder why nobody responds.

The emails sound like they were written by a corporate marketing bot because, well, they were. AI defaults to this overly professional, buzzword-heavy tone that screams "I didn't actually write this."

The Right Way to Use AI for Email Personalization

Think of AI as your research assistant and first draft writer, not your final copywriter. Here's my current workflow:

Step 1: Let AI Do the Heavy Lifting (Research)

AI is actually incredible at analyzing websites and finding specific details. It can scan a homepage in seconds and identify:

Technical issues (slow load times, broken links, mobile problems)
Missing features (no online booking, outdated copyright, no SSL)
Industry-specific opportunities (SEO gaps, conversion issues)
Business context (who they serve, what makes them different)

This part used to take me 30-60 minutes per prospect. Now it takes less than 5 minutes. That's where AI shines.

Step 2: Get the AI First Draft

Let AI write the initial email based on what it found. But here's the key: you need to give it constraints.

Good AI prompt:

"Write a casual, 100-word cold email to a local contractor. Mention the specific mobile speed issue you found. Sound like a helpful human, not a salesperson. No buzzwords like 'leverage' or 'synergize.' Get to the point fast."

Bad AI prompt:

"Write a professional email about this website."

Step 3: Humanize It (The Most Important Part)

Here's what I always change in AI-generated emails:

Remove corporate speak

AI writes: "I hope this email finds you well"

I change to: "Hi Jennifer," (just start, no fluff)

Kill the buzzwords

AI writes: "Enhance your digital presence and maximize online potential"

I change to: "Fix your site so more people actually book appointments"

Add contractions

AI writes: "I noticed you are not using..."

I change to: "I noticed you're not using..."

Make it conversational

AI writes: "Would you be interested in discussing this further?"

I change to: "Want to hop on a quick call about it?"

Step 4: Add One Personal Touch

This is what separates you from the 99% of people just copy-pasting AI outputs. Add ONE thing that AI couldn't possibly know:

"I was actually searching for local plumbers and came across your site..."
"Saw your post about [recent event] on LinkedIn..."
"A colleague recommended your services..."
"I'm based in [same city] and noticed your office on Main St..."

That one sentence proves you're a real person who actually looked at their business, not a bot sending 1,000 emails.

Before & After: Real Example

What AI Generated (First Draft):

Dear Business Owner,

I hope this email finds you well. I recently had the opportunity to review your website and was impressed by your comprehensive service offerings. However, I noticed several areas where technical optimization could significantly enhance your user experience and conversion rates.

Specifically, your mobile page load time is currently 8.4 seconds, which research indicates results in a 40% bounce rate impact. I specialize in performance optimization for local service businesses and would be delighted to discuss how we might collaborate to maximize your digital presence.

Would you be available for a consultation to explore these opportunities?

What I Actually Sent (After Editing):

Hi Mike,

I was searching for a local electrician and found your site. Good reviews, but heads up: your site takes 8 seconds to load on my iPhone. That's probably costing you a lot of calls from people who give up and go to the next Google result.

I help local contractors fix these kinds of tech issues. Want to hop on a 15-minute call this week? I can show you exactly what's slowing it down.

Corey

Same information. Same offer. Completely different tone. The second one got a response in 4 hours.

Red Flags That Your Email Sounds Too AI

If your email has any of these, rewrite it:

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Starts with "I hope this email finds you well" or "I hope you're doing well"

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Uses words like "leverage," "synergize," "maximize," "optimize," "enhance"

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Says "Dear [Title]" instead of just using their first name

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Longer than 150 words (AI loves to ramble)

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Uses "I would be delighted" (nobody talks like that)

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Multiple exclamation points trying too hard to sound enthusiastic!!!

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Ends with "Looking forward to synergizing" or similar corporate nonsense

The Read-It-Out-Loud Test

Here's my #1 rule before sending any AI-assisted email:

Read it out loud. If you wouldn't say it to someone's face, rewrite it.

Seriously, try it. Read your email out loud like you're talking to someone at a coffee shop. If it sounds weird or overly formal, your recipient will think it sounds weird too.

When AI Actually Makes Things Worse

Don't use AI for:

Follow-up emails: These need to reference specific details from previous conversations. AI doesn't have that context.
Responding to replies: If someone responds to your cold email, write back yourself. Don't AI-generate a response. That's lazy and obvious.
Emails to people you actually know: If you've met them before or had any previous contact, write it yourself.
Apology or sensitive emails: If something went wrong or you're addressing a complaint, AI will make it worse with generic corporate apology language.

How I Use AI Now (ThawMail)

After 3 months of building and experimenting, I built ThawMail to solve exactly this problem. It does the research and writes a solid first draft, but with guardrails:

Analyzes websites for specific, real issues (not generic observations)
Writes in a conversational tone (no "synergizing")
Keeps emails under 150 words
Focuses on one problem and one solution
You still review and add your personal touch before sending

Saves me hours per week targeting local small businesses, and my response rate actually went up to 12-15% because the AI finds problems I'd miss doing manual research. Built with Next.js, TypeScript, OpenAI API, and Puppeteer for automated website analysis.

Try ThawMail Free (3 Credits)

The Bottom Line

AI is a tool, not a replacement for thinking. Use it to save time on research and first drafts, but always add the human touch before hitting send.

The web developers and freelancers who succeed with AI-assisted outreach aren't the ones using it to send 500 emails a day to everyone. They're the ones using it to send 20 well-researched, personally-reviewed emails to local small businesses that sound like a real human wrote them.

Because at the end of the day, people hire people. Not bots.