Session Engineering: The AI Skill No One Talks About
How to Build Smarter, Faster, and More Efficient Workflows
Everyone’s talking about prompt engineering—how to phrase a question just right so AI spits out something useful. But after months of experimenting with ChatGPT and other tools, I’ve found that one-off prompts are the wrong way to use AI.
The real power? Session engineering.
Instead of starting fresh every time, open a new session, drop in your context, and build on it. Every interaction refines the output. Every response gets smarter. If you’ve ever been frustrated by generic AI answers, this might be the shift you need.
Here’s why it works—and how to make it work for you.
The Problem with One-Off Prompts
Most people treat AI like a search engine. They type in a request, get a response, and move on. And sure, that works—for surface-level tasks like summarizing an article or brainstorming social media captions.
But for anything requiring depth or continuity, it falls apart fast.
Lack of Context → Every time you start a new chat, you wipe the slate clean. AI doesn’t remember what you’re working on.
Generic Responses → Because AI lacks your history, it defaults to broad, middle-of-the-road answers.
Missed Opportunities → The best insights come from refining, iterating, and layering details over time. One-and-done prompting skips that process entirely.
This is where session engineering comes in.
Why Sessions Matter
Think of an AI session as an ongoing brainstorming session. Instead of expecting one perfect answer, you’re building toward the best result—one message at a time.
When you keep a session open, you:
✔ Give AI a memory (sort of). While ChatGPT can’t remember across different sessions, it can recall everything from the current conversation. This means each response is shaped by the history you’ve provided.
✔ Refine and iterate. A first draft is never the best draft. Instead of treating AI like a magic wand, treat it like a sounding board. Ask for revisions, clarify your goals, and fine-tune the results.
✔ Turn AI into an actual collaborator. The best use of AI isn’t to generate something for you—it’s to generate something with you. When you engage in a back-and-forth, you’re steering the output in a way that one-off prompts never allow.
Real-World Examples of Session Engineering
So how does this look in practice? Here are a few ways I’ve used session engineering to get far better results than single prompts ever could:
1. Writing a Long-Form Article (Like This One)
This post didn’t come from a single request. It started with a rough outline. Then, I asked ChatGPT to expand certain sections, refine others, and punch up weak phrasing. By the time I got here, I wasn’t working with AI’s first draft—I was working with something shaped by multiple rounds of input.
2. Developing a Business Plan
A friend of mine wanted to launch an AI-driven service but had no idea where to start. Instead of dumping everything into one massive prompt, we built the plan step by step in a single session—starting with a rough mission statement, moving to market analysis, then financial projections. Each time we added more detail, the AI could incorporate it into the next stage.
3. Iterating on Marketing Copy
If you ask AI for a product description, it’ll give you something passable. But keep a session open, give feedback, and ask for revisions, and suddenly, it starts matching your brand’s voice. The key is treating it like an intern who improves the more you guide it.
Your AI Session Becomes a Custom GPT
One of the biggest advantages of session engineering is that your AI chat becomes a de facto custom GPT. If you’ve spent time refining a task in a session—whether it’s structuring reports, summarizing meeting notes, or generating a specific style of content—you can reopen that session later and pick up exactly where you left off.
Here’s how it works:
🔹 You refine a task. Say you spend time in a session perfecting how AI structures a client proposal, tweaking the language until it’s just right.
🔹 You revisit the session later. Instead of starting from scratch, you simply reopen that session and say, “Now do the same for this: [insert new details].”
🔹 AI already knows your preferences. Because it has the previous back-and-forth, it remembers the style, structure, and level of detail you want—saving you from repeating the long dialogue you originally had to get it right.
Example: Replicating a Repetitive Task
Let’s say you send out weekly newsletters. The first time, you work through multiple drafts, guiding AI on your preferred tone, format, and structure. Once you’re happy with the result, you save the session.
Next week, instead of explaining everything again, you reopen that session and say, “Now do the same for this week’s topic: [insert topic].”
AI instantly applies what it learned from last time, giving you a polished draft from the first response rather than needing extensive back-and-forth.
Turning Sessions into a True Custom GPT
If you find yourself frequently returning to the same types of tasks, you can take it a step further:
1️⃣ Hold onto valuable sessions. Keep them organized so you can return if needed.
2️⃣ Refine them over time. Each time you revisit, tweak, and improve the process.
3️⃣ Use them as a foundation for a Custom GPT. If the task is essential to your workflow, you can upload your refined instructions and sample outputs into a real Custom GPT, eliminating the need for manual adjustments entirely.
This approach turns your AI use into a well-oiled system—one that improves with every session instead of starting over each time.
AI Isn’t an Answer Machine—It’s a Thinking Partner
Most people don’t get impressive results from AI because they treat it like a vending machine: insert a prompt, get a result, and walk away.
The real power comes when you treat AI like an ongoing conversation—one where each message builds on the last.
That’s session engineering.
And once you start using it, you’ll wonder how you ever did without it.
Hopefully, this post will help you get more out of your AI sessions. If it did and you’d like to see more like it, consider subscribing for more tips and tricks.