The C.I.G.A.R. Method: Stop Writing Prompts, Start Rolling Them
Everyone has an AI guide. Nobody has a hum-AI-dor. Here is how premium tobacco taught me to tame the algorithm.
Everyone is using AI now. ChatGPT, Claude, Gemini... they are everywhere.
But here is the problem: most people are getting terrible results.
They type vague questions and get vague answers. They ask for “content” and get generic slop. They treat AI like a magic box and wonder why the magic never happens.
The issue isn’t the AI. It’s the prompt. And most people have no idea how to construct one properly.
Here is where things get unconventional: I figured this out because of cigars.
I stream a cigar show called Meet in the Middle Cigar Show with my wife Hyacinth and our friend LeeMack912. We smoke, we talk, and increasingly, we experiment with AI live on stream. Watching Leander chat with his AI bot in real-time, listening to Hyacinth research tobacco origins, and using it myself, it all clicked.
AI prompts work exactly like premium cigars.
Bad construction? The whole thing falls apart. Miss a critical component? You get a terrible experience. But roll it correctly, and you get something exceptional every time.
I broke this down into a framework I call C.I.G.A.R., and once you understand it, your AI outputs will transform.
The Anatomy of a Perfect Prompt
Think about a well-constructed cigar. It isn’t just tobacco leaves thrown together. There is a Box, a Band, Filler, a Wrapper, and a Binder, each serving a specific purpose.
Your AI prompt needs the same precision.
C: Context (The Box)
“Set the Stage”
When you grab a cigar box off the shelf, it tells you everything before you even open it. A dress box signals luxury. A cabinet suggests age and care. The packaging sets expectations.
In AI: Context is your background information. Don’t just ask a question, set the scene.
❌ Bad: “Write about productivity.”
✅ Good: “I’m writing for mid-level managers at SaaS companies who are drowning in meetings and looking for practical time management strategies.”
The second prompt gives the AI a world to work within. It knows the audience, the pain point, and the environment.
On our show, Hyacinth doesn’t just review a cigar, she researches the farm, the family, the region. That context transforms a simple smoke into a story. AI works the same way.
I: Identity (The Band)
“Define the Voice”
The band tells you what you are smoking. A Padrón 1964 Anniversary. An A.J. Fernandez New World. It establishes authority and sets expectations for quality.
In AI: This is your persona. Who should the AI be?
❌ Bad: “Explain machine learning.”
✅ Good: “Act as a patient university professor explaining machine learning to business students with no technical background.”
The persona shapes everything: word choice, complexity, tone.
Think about our show: I analyze construction and deduce origins. Hyacinth brings nuanced historical research. Leander gives blunt, contrarian takes with zero fluff. Same topic, three completely different voices. Tell the AI which voice you need.
G: Goal (The Filler)
“The Substance”
The filler is the meat of the cigar, ligero for strength, viso for flavor, seco for burn. Without quality filler, you are smoking air.
In AI: This is your task. What do you actually want?
❌ Bad: “Help me with email.”
✅ Good: “Write a 150-word follow-up email to a potential client who went silent after our demo three weeks ago. Acknowledge the gap, provide value, and suggest a specific next step.”
Vague goals produce vague outputs. Specificity is everything.
When LeeMack912 uses AI on stream, he doesn’t say “tell me about this cigar.” He asks specific questions: “Compare the Nicaraguan tobacco in this blend to similar puros from Estelí.” Well not always, he usually messes with it, (it’s entertainment) but specificity gets results.
A: Atmosphere (The Wrapper)
“The Flavor Profile”
The wrapper provides up to 80% of a cigar’s flavor. Connecticut shade tastes creamy and mild. Habano wrapper brings spice and complexity. The wrapper determines how everything else is experienced.
In AI: This is your tone and style. How should the output feel?
❌ Bad: Generic corporate-speak.
✅ Good: “Write in a conversational, slightly irreverent tone. Use short sentences. No jargon. Sound like you’re explaining this to a smart friend over coffee.”
The wrapper changes everything about how content lands with readers. Hyacinth doesn’t say “this cigar is good”, she describes it like a sommelier describes wine. The wrapper is the flavor. Tell AI what flavor you want.
R: Restrictions (The Binder)
“Hold It Together”
The binder is the unsung hero of cigar construction. It holds the filler bunch together and ensures an even burn. If the binder fails, the cigar tunnels, canoes, or falls apart completely.
In AI: These are your constraints, the guardrails that keep output focused.
❌ Bad: Letting AI ramble for 1,000 words.
✅ Good: “No corporate buzzwords. No bullet points. Under 300 words. Use active voice only.”
Constraints force clarity. They eliminate what doesn’t belong.
I use deductive reasoning to analyze cigars, eliminating what doesn’t fit until I identify the tobacco, the origin, the construction. The binder does the same thing for prompts. It keeps structure tight so your output burns clean.
Let’s Light It Up: Full Example
Here is how I would use the C.I.G.A.R. Method to generate content for this very blog:
Context: I’m writing for business professionals subscribed to my tech blog who value creative, humanized approaches to AI.
Identity: Act as an experienced technologist who teaches through unconventional metaphors and real-world examples.
Goal: Write a 200-word explanation of why AI “hallucinations” happen and how to reduce them.
Atmosphere: Conversational and clear. No academic jargon. Use analogies that click immediately.
Restrictions: Under 200 words. No bullet points. Don’t use the phrase “large language model.”
The AI Output:
“AI doesn’t ‘know’ things the way you do. It predicts what word comes next based on patterns it saw during training. When you ask it something obscure or give it zero context, it fills gaps with plausible-sounding nonsense, that’s a hallucination.
Imagine asking someone to describe a restaurant they’ve never been to. They might say ‘it probably has tables and serves food,’ which is technically true but completely useless. To reduce hallucinations: be specific, provide context, and ask the AI to cite sources or admit when it doesn’t know. The more constraints you give it, the less room it has to improvise badly. Think of it like this, if you hand someone vague instructions and expect perfection, you’ll be disappointed every time. AI is powerful, but it’s not psychic.”
See that? Perfectly structured. On-brand. Ready to publish.
The Bigger Picture
You just learned prompt engineering through cigars. That is the point.
The best learning doesn’t always come from the expected places. Sometimes a hobby teaches you more about your profession than another certification course. Sometimes sitting with friends, smoking, and experimenting with AI on a livestream reveals patterns you’d never notice staring at a screen alone.
Next time you open ChatGPT or Claude, don’t just type and hope.
Set the Context. Define the Identity. Nail the Goal. Flavor it with Atmosphere. Bind it with Restrictions.
C.I.G.A.R. it.
Roll it right, and you’ll get a perfect draw every time.
Venga!
Mark (VengaDragon)
I co-host Meet in the Middle Cigar Show with Hyacinth LaPanatela and LeeMack912, where we explore cigars and the unexpected place where the AI and cigars intersect.
🔧 Manage Your Subscription
Remember, VengaDragon is a magazine, not a newsletter. You are the editor of your own inbox.
I publish across five distinct columns. If you love the Tech Stack stuff but hate the AI stuff, you don’t have to unsubscribe. You can simply “mute” specific sections in your account settings.
🥅Big Goal
The Mission: I have a wildly ambitious goal to hit 500 by January 1st.
I am building this in public, starting from zero. No ads, no tricks. Just this lab report.
Enjoy your week! Share this someone who would enjoy it…
THIS is mad cool! My favourite is "I." Making sure that you get AI to recognise and understand the tone of your project/writing is the difference between success and failure. The same can be said of cigars. Master blenders know what they want to achieve when blending a cigar and only occasionally step into that happy accident.