Let’s talk about the “Almost Perfect” first draft.

You’ve done your homework. You used the 5-step TCREI framework. You maybe even stole one of our prompts from the last article. You get a response back from the AI, and it’s… pretty good. It’s a solid B-. But it’s not quite what you had in your head. The tone is a little off, it missed a key detail, or it’s just a bit too long.

Right here is where most people stop. They either accept the B- draft and spend 20 minutes editing it themselves, or, even worse, they get frustrated, close the window, and start a brand new prompt from scratch. This is the biggest—and most common—mistake you can make.

It’s time for a mindset shift.

Stop treating AI like a vending machine where you put in one coin for one result. Start treating it like a brand new, super-fast, incredibly literal-minded intern.

Your first prompt is the initial briefing. Everything that comes after is the feedback that turns your intern’s decent first effort into a brilliant final product. The real magic isn’t in the first prompt; it’s in the conversation that follows.

The Art of the Follow-Up: 4 Conversational Moves to Get What You Want

Think of this as your guide to managing your new AI intern. These are the four most common and powerful conversational moves you can make to guide the output exactly where you want it to go.

1. Refine the Tone & Style

This is for when the AI gets the “what” right, but not the “how.” It’s about changing the feeling of the content.

Simple Follow-Up Prompts:

- "That's a good start, but make the tone more professional."

- "Can you rewrite that to sound more witty and less formal?"

- "Use simpler language. Write it so a 10th grader could understand it."

2. Add, Remove, or Replace Information

Treat the AI’s response like a living document. You are the editor-in-chief, and you can make any changes you want.

Simple Follow-Up Prompts:

- "This is great. Now, add a new paragraph about our 5-year warranty."

- "Remove the second bullet point and replace it with a sentence about our free delivery."

- "Expand on the part about 'sustainability.' What does that actually mean for the customer?"

3. Change the Format on the Fly

This is one of the most powerful, time-saving moves you can make. The content is good, but you need it in a different package.

Simple Follow-Up Prompts:

- "I love this. Now, take these three paragraphs and turn them into a bulleted list."

- "Can you format this information as a two-column table?"

- "Rewrite this as a script for a 30-second video."

4. Ask It to Explain Itself (The “Chain-of-Thought” Primer)

This is a great move for brainstorming, but it’s also your entry point into a more advanced technique. By adding one simple phrase, you can dramatically improve the quality of the AI’s output, especially for complex tasks. That phrase is: “Explain your reasoning step-by-step before you give me the final answer.”

This is a simplified version of a technique called “Chain-of-Thought” prompting. It forces the AI to “show its work” and think more logically, which often leads to more creative and accurate results.

Simple Follow-Up Prompts:

- "Why did you choose those three specific points? Explain your reasoning step-by-step."

- "I need three taglines for my business. Before you give them to me, explain your thought process for how you'll create them."

Canadian AI Guy’s Pro Tip: Want to turn your AI into a strategic sparring partner? Use the “Devil’s Advocate” technique. After the AI gives you an idea you like, hit it with this follow-up: “Now, act as a skeptical customer and tell me three reasons why this idea might NOT work or what concerns I might have.” This is a powerful way to stress-test your own ideas and find weak spots before you go to market.

Putting It Into Practice: A Real-World AI Conversation

Let’s watch our AI intern in action. Imagine you’re Small Business Steve, and you want to write a welcome email for people who just signed up for your hardware store’s newsletter.

Round 1: The Initial Prompt

Steve writes a solid first prompt using the TCREI framework, asking for a welcome email that’s friendly, mentions the store’s history, and offers a small discount.

Round 2: The B- Draft

The AI returns a functional but generic welcome email. It hits all the points, but it sounds a bit like a corporate robot wrote it.

Round 3: The First Follow-Up (Refining the Tone)

Steve replies: That’s a good start, but it sounds a bit corporate. Can you rewrite it in a more friendly, neighbourly tone? And add a bit about how my grandfather started the store in 1978.

Round 4: The A- Draft

The AI returns a much better version. The tone is perfect—warm and welcoming. But it’s a little long. Steve knows people skim emails.

Round 5: The Final Follow-Up (Refining the Format & CTA)

Steve replies: Perfect. Now, just shorten it by about 25% and make sure the final call to action is a clear P.S. that offers them a 10% off coupon for their first visit.

The A+ Result: In three quick, conversational steps, Steve has guided the AI from a generic template to a perfect, personalized email that sounds exactly like him and is ready to send. That’s the power of iteration.

The A+ Move: Turning One Good Draft into Five Pieces of Content

Now for the “aha!” moment. You don’t have to stop with one perfect email. A single, successful conversation can become the source for a week’s worth of marketing content. This is the “Creative Remix,” and it’s a massive force-multiplier for any busy business owner.

Let’s take Steve’s perfect A+ email and remix it.

Follow-Up Prompt #1: The Social Media Remix

This is great. Now, take the core message of this email and turn it into three short, witty Instagram posts. Include relevant hashtags.

Follow-Up Prompt #2: The Blog Post Remix

Excellent. Now, use the theme of "a family-run store that's been part of the community for generations" from the email and brainstorm 5 blog post titles based on it.

Follow-Up Prompt #3: The Video Script Remix

I love those ideas. Take the blog title 'Three Lessons Our Grandfather Taught Us About DIY' and write a script for a 30-second TikTok or Instagram Reel based on it.

In just a few extra minutes of conversation, you’ve turned one well-crafted email into a whole content campaign. That’s not just working smarter; it’s a whole new way of working.

Knowing When to Start a New Conversation

This is the final, crucial piece of the puzzle.

Think of each chat you have with an AI as a single, continuous conversation with your intern. The AI “remembers” everything you’ve talked about in that specific chat. This “memory” is often called its context window, and it’s amazing for refining a single task.

But if you suddenly switch from your email campaign to brainstorming a new product name in the same chat, your intern can get confused. The old context might “bleed” into the new task, leading to weird or irrelevant results.

The rule is simple: One task, one conversation. When you’re ready to start something completely new, just hit that “New Chat” button. This gives your AI intern a fresh, clean slate.

The Ultimate Power Move: Give Your AI a Permanent Brain

Everything we’ve discussed so far is about managing your AI intern on a project-by-project basis. But what if you could give your intern a perfect memory? What if you never had to repeat the basics about your business ever again?

You can. It’s a feature called Custom Instructions (or sometimes a System Prompt), and it’s the single most powerful, under-used tool for any business owner.

Think of it as your intern’s permanent employee file. You write down the core details about your business and your preferences once, and the AI remembers it for every future conversation.

Your Copy-and-Paste Custom Instruction Template

Here’s a template designed for a Canadian small business. Go into your AI tool’s settings, find “Custom Instructions,” and paste this into the two boxes, filling in the blanks.

Box 1: What would you like the AI to know about you to provide better responses?

My name is [Your Name] and I am the owner of [Business Name], located in [City, Province]. We are a [Your Industry, e.g., local hardware store, financial advisory firm, etc.].

Our Mission: [A simple one-sentence mission statement, e.g., "To provide our community with reliable products and friendly, expert advice."]

Our Products/Services: We specialize in [List 2-3 key products or services].

Our Target Audience: Our ideal customers are [Describe your target audience, e.g., "homeowners aged 30-60 in the Fraser Valley who value quality and durability."]

Our Brand Voice: Our tone is [Choose 3-5 adjectives, e.g., "friendly, helpful, trustworthy, and a little bit humorous."]

Box 2: How would you like the AI to respond?

Always adopt the brand voice I described above.

Keep paragraphs short (2-3 sentences max) for easy readability online.

Avoid overly formal language and complex jargon. Explain concepts simply.

When generating marketing copy, always end with a clear call to action.

Structure longer responses with clear headings and bullet points.

Setting this up takes five minutes. It will save you hours every single month.

And this is just the beginning. The next evolution of this concept involves creating specialized “brains” for different parts of your business using tools like ChatGPT’s GPTs, Google’s Gems, or Projects in platforms like Claude. We’ll be diving deep into these advanced tools in a future article in our Playbook.

Conclusion: You Are the Director

The real skill in using AI effectively isn’t just writing that first perfect prompt; it’s about artfully guiding the conversation that follows to turn the AI from a simple order-taker into a true creative partner.

You are the boss. You are the director. The AI is a powerful actor, but you’re the one telling it how to perform. Use these conversational moves to steer the output until it’s exactly what you need, turning B- drafts into A+ assets every single time.

Try having a real back-and-forth conversation with an AI this week. Now that you know how to talk to it, our next article will show you an incredibly powerful way to use that skill with ‘Stop Wasting Time: Using AI to Summarize Reports, Emails, and Meetings.’

Frequently Asked Questions (FAQ)

1. Does ChatGPT remember what I said earlier in a conversation?

Yes, within a single chat session, AI models like ChatGPT have a “context window” that allows them to remember previous parts of the conversation. This is what makes iterative, back-and-forth refinement possible.

2. What’s the best way to ask an AI to revise its own answer?

Be direct and specific. Instead of saying “I don’t like it,” tell it why. For example, “That’s a good start, but can you make the tone more casual?” or “Please remove the third paragraph and add a point about our free shipping.”

3. How do I get an AI to change the tone of its writing?

Use descriptive adjectives. Simple follow-up prompts like “Make it more witty,” “Rewrite this in a professional and formal tone,” or “Make it sound more empathetic” work very well.

4. Why should I start a new chat for a new task?

Starting a new chat for a new task prevents “context bleed.” It ensures the AI’s “memory” from a previous task (like writing a social media post) doesn’t confuse its ability to perform a completely different new task (like brainstorming product names).

5. What if the AI gets stuck on a wrong idea or fact?

If a simple correction (“That date is incorrect, please use 2024 instead”) doesn’t work, it’s often best to start a fresh chat. This clears the AI’s context window and allows it to approach the problem without the “memory” of the incorrect information. Personally though, it might be best to use a prompt for a platform called Perplexity to find a relevant current stat for that section. We’ll cover Perplexity for Research in another blog as well.