The AI Optimist
The AI Optimist
🚀 Engage, refine, and iterate – AI Case Study: Co-creating Powerful Emails - Ep 5

🚀 Engage, refine, and iterate – AI Case Study: Co-creating Powerful Emails - Ep 5

Asking the right questions to transform vague emails to conversational email with ChatGPT. Avoid common mistakes that undermines what you create with any content!

How does an old tool like email even last in the time of AI? Because everybody has an email, and as all the Creator Economy have recently discovered, it’s a powerful way to keep in touch that you control.

So you build a following on social media. You see others with thriving businesses driven by email, so you start. —staring blankly at an email draft, fingers hovering over the keyboard, unsure of how to begin, what to say?

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Go to ChatGPT, right, but what questions do you ask beyond writing me an email? What is so important to understand about AI? It would help if you asked the right questions.

A common misconception is that the AI’s marketing language, taken from the vast trove of emails others have written (often poorly), is the gold standard. 

And it reflects what’s most common, not what’s most effective. If you want your emails to stand out and resonate, you’ve got to infuse them with more than just ChatGPT’s initial suggestions.

One of the challenges in creating any content, especially marketing, is understanding what an excellent AI-generated email should include. Many make this mistake, having negative ideas about marketing.

It’s like setting off on a road trip. Sure, you’ve got the car (ChatGPT) that can take you anywhere, but you—the driver—need to decide the destination and the best route to get there. 

By actively interacting and directing the conversation, you can guide ChatGPT away from the ‘main roads’ of average language and onto the ‘scenic routes’ of tailored impactful communication.

But why is asking the right questions so critical? The answer is simple. ChatGPT responds based on the cues you provide. 

Vague questions might lead to generic answers—like expecting a chef to create a gourmet dish without specific ingredients. So, to truly leverage this AI’s potential, you’ve got to dig a little deeper, refine your approach, and sometimes even challenge its first responses.

ChatGPT is a tool, a treasure trove of data and language patterns. But it doesn’t know the best way to communicate your unique message. That’s where you step in. Your guidance and strategic questioning mold its responses to perfectly fit your vision.

So, as we delve into this interactive email case study, remember you’re not just a bystander. You’re an active participant, a co-creator. Together with ChatGPT, you begin crafting emails that convey information and capture essence and intention.

Ready to start? The power is in your hands—let’s put it to good use!

Craft your email as a conversation, not a monologue. By blending AI’s breadth with your straightforward questions, create tailored messages that resonate deeply and stand out compared to generic emails that sound like everyone else.

Questions have the potential to guide thinking, stimulate curiosity, and promote more profound understanding.

The type of question you ask will affect the way ChatGPT responds.

  • It is essential to be aware of your own biases when asking questions.

  • Weak emails are standard because people don’t understand what a good one is, which is why this case study will help.

  • Questions should be clear, concise, and free of jargon.

Case Study Overview: Writing an AI-generated Email to Contact a Possible Partner to Promote an SEO Tool

For partnerships, outreach involves contacting busy people who have little time. You need to get to the point in the subject line, and first two sentences, as that is all people will read before deciding to delete your message or respond.

What follows is how I used ChatGPT to create an email, the inadequate responses I had to improve with follow-up questions, and applying this same method to anything you make with AI.

Here’s my detailed initial prompt, which also created a mediocre ChatGPT, as you’ll see below.

The email involves a Subject Line and the actual words used in the email. The Subject Line is what you see before you open the email and is one of the deciding parts of whether anyone even reads the email. Remember this importance as you proceed.


Acting as an affiliate manager for an SEO tool company creating search content with AI, write a 3 paragraph email in a friendly and professional voice, inviting a longtime SEO expert who rarely recommends tools into the affiliate program and offering a private trial to make sure the expert likes the SEO AI Tool. Be sure to include that both the affiliate program and the SEO expert are quite picky about who they choose to partner with, and encourage a follow up meeting or questions so both sides can see if it’s a fit. 

ChatGPT First Response

Subject: Exclusive Invitation to a Unique Partnership with Our AI-powered SEO Tool

Dear [SEO Expert’s Name],

I hope this message finds you well. I’m reaching out to you today because I deeply admire your expertise in the field of Search Engine Optimization. As an authority in this domain, your insight and discernment have been invaluable to the industry, and we appreciate your judicious approach to recommending tools.

I’m writing as the Affiliate Manager for [Your Company], a leading SEO tool company that’s revolutionized the field with advanced AI-powered technology. We’ve been quite discerning in our choice of collaborators, much like you’ve been with your endorsements. Given your profound understanding of SEO and our shared commitment to quality, I’m excited to extend an invitation to you to join our exclusive affiliate program. I’d also like to offer you a private trial of our SEO AI Tool, allowing you to experience firsthand the innovation and efficiency our tool can bring to any SEO work.

We understand the importance of ensuring a fit that aligns with both our values, and hence, would welcome an opportunity to discuss this partnership further. If you’re open to exploring this potential collaboration, or if you have any questions about our tool or the affiliate program, please don’t hesitate to reach out. I’d be more than happy to arrange a follow-up meeting at your convenience to address any inquiries you may have and to walk you through the unique features of our SEO AI Tool.

Looking forward to hearing from you soon, and I truly believe this partnership can bring about incredible value to both our audiences.

Best regards,

Readability Stats mean how easy is this to read? It reads at a 12th grade level when 5-7th grade is preferred. Notice the words per sentence, too much!

And the Flesch Reading Ease is 44.8, too low!

This email is long and starts with the words many uses, which gets you put into spam: 

“I hope this message finds you well.”

I hope this message finds you well….snore.

Yes, it’s good to care, but this is not nice when reaching out and seeing this or a similar line (see the bottom of this article to see what not to do).

It’s trying to prove you’re a nice person. Google will often immediately put emails with this or similar opening sentences into spam because spammers use it.

Like creating anything with ChatGPT or any AI, you must ask follow-up questions to get the best content. Please read this and know that I know how to connect with people using email for over 20 years, so read my instructions to understand what a good email should contain. 

Follow-Up Question

Rewrite this to be half the length, using bullets to outline key elements and avoid polysyllabic words and sales sounding language.

This needs to be more genuine, personal, and approachable, and less of the verbose language and praise for the SEO expert....

Inject curiosity language to encourage exploring and gaining feedback from the SEO expert, even if they don’t partner.

2nd ChatGPT Response

Subject: Invitation: Try Our AI SEO Tool & Possible Affiliate Partnership

Hello [SEO Expert’s Name],

I hope you’re doing well. I’m [Your Name], Affiliate Manager at [Your Company]. I’ve seen your work, and it’s impressive. We’d like to talk about a potential partnership.

Here are the key points:

● We’ve developed a new AI SEO tool.

● We’re being selective about who we partner with, just like you are with your recommendations.   

If you like it, we’d be thrilled to have you join our affiliate program.

Let’s chat about it and answer any questions you might have. I’m available for a call or video meet whenever you’re free.

Look forward to hearing from you, 

Readability Stats mean how easy is this to read? It reads at a 7th grade level, better!

And the Flesch Reading Ease is 67, much better!

I made a mistake by not instructing it not to include that awful first sentence.

Follow-Up Question 3

Do not use “hope you’re doing well” or anything like it for the first sentence, avoid saying who the sender is and company name, treat this more like a text message than an email.

Add a sentence on how the SEO AI tool isn’t full of hype like most AI and has been around for 7 years, and we’d like to earn the SEO expert’s trust by showing them the tool, giving them a monthly recurring commission of 25% on any sales, with a 60- day cookie and last click attribution.

Rewrite and inject curiosity language to encourage exploring and gaining feedback from the SEO expert, even if they don’t partner. We learn and the SEO expert learns in a quick review, with the goal to be affiliate partners.

Rewrite in a casual and conversational tone.

3rd ChatGPT Response

Subject: Invitation: Private Pass🔹Test Drive AI SEO Tool & Link Up?

Hey, as you review SEO tools, what about one that cuts tedious SEO content creation by 40% or more?

Our AI Tool has been delivering SEO results for 7 years, minus the AI hype. The net result is content that Google eats up like (digital) candy.

👉 We’re picky about our affiliate partners, just like you’re selective about the SEO tools you endorse.

And your experience and savvy is why we’re reaching out:

🔹 Please take a free spin with this Private Pass; see if it earns your trust. - URL

🔹 Like it? Consider joining our affiliate program.

🔹 Perks include a 25% recurring commission on any sales, 60-day cookie click attribution.

Keen to talk more and answer any queries you might have....

This is the best it could get with ChatGPT; I did some rewriting, but it’s not bad. This email is short, focuses on the person being contacted.

This email could be improved by being more personal, and less talking about the SEO tool. Talk to the person getting the email, what’s important to them, and get them to reply or respond so THEN you can share what’s important about you.

Remember it’s always about who you are sending it to, and not about you. That’s a key to any email, marketing or otherwise - even someone you work with.


1. Good Questions, Good Responses: be specific, let ChatGPT know what role to play – in this case, the one sending the email - to gain focus.

2. Set the tone: AI needs to know what you want the response to sound like. Be clear. Details!

3. Ideas are where you save time – get new ideas and angles to create your content. 

My best advice is to take what you get and personalize it in your voice, who you are, that’s what sets you apart.

Conclusion & Recommendations for Writing Content with ChatGPT - Emails and all

• Begin with a clear intent for what you want to know.

• If you’re unhappy with an answer or find it too general, rephrase or specify further.

• For contentious or subjective topics, request multiple perspectives to get a rounded view.

• Always fact-check critical information. ChatGPT can provide a lot of information but isn’t infallible.

•Remember, the model is as good as the clarity of the question. A well-phrased question is more likely to yield a comprehensive answer.

Merging AI and Authenticity in Email Mastery

This case study in the art and science of email writing in collaboration with ChatGPT shows how to make it work for you. Let’s revisit the cornerstones of our discussion:

  1. Start with Authenticity: Crafting an email should feel like a dialogue. On this two-way street, genuine connection takes priority over broadcasting a one-sided message.

  2. AI as a Tool, Not a Crutch: ChatGPT offers rich information and linguistic patterns. However, guiding and refining its responses is essential to ensure they align with your unique brand voice.

  3. The Importance of Question Precision: Make sure your questions are well-defined. A vague question may lead to a generic answer, whereas specificity can be the key to tailored insights.

  4. Blend the Breadth and the Unique: While ChatGPT provides knowledge, your individual touch and perspective make emails resonate.

  5. Challenge the Initial Response: Don’t just settle for the first answer. Dig deeper, ask follow-up questions, and steer the AI toward the nuanced response you’re aiming for.

To harness the power of email, work as a copilot with ChatGPT. The real magic happens in the dance between human creativity and tech prowess. 

Next time you write an email draft, remember: Don’t just throw a question into the abyss and hope for brilliance. Engage, refine, and iterate. 

The key isn’t in asking a question—it’s in the art of the follow-up. With this partnership approach, you craft emails that inform and inspire.

BONUS – Email Best Practices to Understand for ChatGPT

  1. Your Subject Line: When someone gets your email, the first thing they do is ask, why is this important?

    This is where the subject line comes in; most businesses focus all their time on the email’s copy and look/feel, not realizing that if the subject line stinks, no one reads it. 

  2. Make Your Email Like a Postcard: One of the common questions I get is how long an email should be.

    While long emails can sometimes work, keeping it brief, like a postcard, is most often recommended. Be sure to put a blue link at the top and bottom of the email, and don’t rely on graphics.

    Often these images are hidden from people up front, and the email should work with and without graphics.

  3. Your Subject Line; Do I repeat myself? Of course, I do, because you need to think about this first. So many send an email at the last minute and rush to write a subject line as if it’s the last chore.

    It is the first task, the defining moment of whether your email is opened, the real test you are facing. Check out subject lines constantly and play with them to encourage people to open by adding value.

    Tricking them is easy, but if you trick and disappoint them, they will hit the Spam button on you quickly.

  4. Your First Sentence: This is a lesson from journalism and direct marketing. Your first sentence is the second barrier and should flow from the subject line.

    Just like someone searches for a keyword at Google and looks for that keyword on the page they go to, a person who sees a good Subject Line wants that headline immediately reinforced in the first sentence.

    Lose them here, and you not only lose their interest, but boredom also leads to hitting the Spam button, which hurts your chances of getting delivered to others.


Bad (and Most Common) Email Ledes (first sentences)

DO NOT use these, and see how often you see them!

Hello my name is FIRSTNAME from COMPANY TAGLINE)

Hope you are doing great!

I hope you don’t mind me being direct but I just had to ask

I hope all is well with you

Hope your week is off to a great start

Hope you had an amazing weekend

(HOPE: To wish for a particular event that one considers possible.)

The AI Optimist
The AI Optimist
Moving beyond AI hype, The AI Optimist explores how we can use AI to our advantage, how not to be left behind, and what's essential for business and education going forward.
Each week for one year I’m exploring the possibilities of AI, against the drawbacks. Diving into regulations and the top 10 questions posed by AI Pessimists, I’m not here to prove I’m right. The purpose here is to engage in discussions with both sides, hear out what we fear and what we hope for, and help design AI models that benefit us all.