Creating my Notion HQ, Step By Step: A Case Study in Real-Time Promptcraft
I've been using ChatGPT and Claude for over a year, getting decent results from my prompts. But "getting decent results" isn't the same as "knowing what I'm doing."
It's like my golf game. Yes, I can drive a ball 220 yards down the fairway — one time out of five. The rest? Worm-burners and slices. There's a difference between getting lucky and succeeding consistently.
I want my promptcraft to be consistent.
Recently, I took a detour from my AI Mastery project to build a project HQ in Notion. That inspired me to take a closer look at my promptcraft as I was doing it—not just what worked, but why.
This exercise made me realize that my prompting style was too influenced by my managing style, which relies heavily on human empathy. That's not always good when you're managing an alien. LLMs require a different type of empathy. (That’s a big insight, and I’m exploring it in an upcoming post.)
This post takes a close look at how I built a complex system using ChatGPT, then had ChatGPT circle back and critique my prompts so I can "hit the ball down the fairway" more consistently.
My own takeaway from this exercise: “vibe prompting” has worked OK for me, but it’s a far cry from a best practice. Now, I’m studying best practices – both in how I develop prompts, and how I understand the partnership between me and the AIs I work with.
The Notion HQ Build: Four Key Moments That Changed My Promptcraft
1. The "Novel-Length Prompt" Problem: Learning to Focus
The Context: I needed to scope out the project system for my entire sabbatical. Multiple moving parts, complex goals, and one human being drowning in his own ambition.
My Original Prompt:
Warning: this is long and sloppy. I'm including only a portion here. The full prompt is in the appendix — you'll thank me for not putting it all here.
For this chat, you are an expert in Project and Program management, and can plan projects down to the last detail and explain them in simple terms to anyone who ISN'T a program manager.
You're also an absolute ninja with the Notion software suite.
I've spent a week studying the basics of Notion, and I think it's an excellent solution for managing all the projects I'll be running as part of my sabbatical (and possibly my work life beyond the sabbatical.) I need to set up the project boards, and I need your help.
It seems to me there are three key, related programs. (Maybe it's just two; I need your opinion.) (blah, blah, blah. It continues for another page. Full text in the appendix.)
What I Got: ChatGPT delivered solid structure—four "big rock" programs with detailed Notion recommendations. But it also produced a "helpful" system diagram that looked like a spider spun it during a particularly bad acid trip.
The Lesson: Even as I typed this prompt, I was thinking, "Man...this is long." To ChatGPT's credit, it understood the assignment — probably due to all the time we've invested in talking about this project.
But I also realized that this was a classic "lucky fairway drive." I need to be more self-aware, and workshop my complex prompts before posting.
ChatGPT's Critique:
I gave strong context and real-world constraints
Long and sprawling; would be easier to answer if broken into two prompts
ChatGPT's Refined Prompt:
I'm managing several related sabbatical projects: AI learning, publishing, networking, and personal/career logistics. I've already created a Blog Idea Tracker, Prompt Library, and Connection Board. Based on your project management and Notion expertise, what are the "big rocks" I should focus on? And what Notion structures would support each?
My reaction: I'm humbled. ChatGPT boiled my prompt down to 50 words. Quite a contrast.
2. The "WTF, ChatGPT?" Moment: When Visuals Go Wrong
The Context: ChatGPT's first diagram of my system, with its component boards, was incomprehensible to humans.
My Prompt:
The diagram is interesting — but too scattershot for me to make any sense of it. Is there something closer to a table view for that? Or can you clean it up, so all related boards and pages are more closely aligned with the Project header? (And maybe color-code by project...)
What I Got: A clean, hierarchical diagram that actually made sense. Color-coded, visually clear, and aligned to how I think.
The Lesson: This time, I knew what was wrong, what I needed, and how to ask for a visual system that makes sense. (This’ll be familiar to every PM I've ever asked for a Gantt chart.)
The "It's interesting but..." preamble made me cringe. It's a relic from my days of directing creatives, who often need a little sugar with their medicine. An LLM doesn't.
ChatGPT's Critique:
Concise, focused feedback
Suggested a solution, not just a problem
Could have added a quick phrase about what made it confusing to me ("hard to see what connects to what")
ChatGPT's Refined Prompt:
The system diagram feels scattered, and I'm having trouble seeing how the HQs and boards relate. Could you reformat it as a table or sidebar-style layout, with one column per project and boards listed below? Color-coding would help too.
3. The Sidebar Hierarchy Crisis: Talking about UX
The Context: Halfway through the build, my Notion sidebar was getting cluttered. Related pages were scattered everywhere, and I couldn't see the logical relationships between different parts of my system.
My Prompt:
One more question. I'm attaching a clip of the sidebar. It's not elegant — I have the Thought Leadership page setup, with different views — but then beneath them, separate, are the full pages for Blog Idea Tracker, Thought Tracker, etc... It feels redundant. Also, just the way my mind works — I like to see the hierarchy of views nested under the master header. Did I do this wrong? If I try to drag the pages under the Thought Leadership header, they show up on the page itself, and it all feels redundant.
What I Got: ChatGPT gave me a clear explanation of how the Notion UI treats pages in the sidebar vs. on the page, plus a workaround using folder-style master pages with collapsible sections.
The Lesson: ChatGPT learned something about me: I like clean visual hierarchies. I like to know how things work. I'm here to learn. Many of its insights about how I like to work clicked with this prompt.
Interestingly: ChatGPT's refined prompt, below, omits those insights. So....maybe a little humanity in the prompt isn't so bad? When is it good to infuse the prompt with my personality?
ChatGPT's Critique:
Honest, specific, and visual (screenshot helped)
Could have clarified: "I'm talking about sidebar behavior, not what shows up inside the page."
ChatGPT's Refined Prompt:
My sidebar is getting messy — all my subpages (Blog Tracker, Thought Tracker) are showing up at the top level instead of tucked neatly under my Thought Leadership HQ. I want them nested under a single folder without embedding them into the page body. How should I organize this?
My reaction: The refined prompt gets to the essence of the problem without the rambling. And it clarifies the sidebar vs. page content distinction.
4. The Meta-Moment: Using AI to Analyze the Human-AI Collaboration
The Context: By the time we'd built several HQs, I realized this process itself was worth studying. So I asked ChatGPT to help me turn our conversation into a case study.
My Prompt:
I want to gather together the prompts in this chat to build an easy-to-read case history of how we built out our first set of Notion boards. Hopefully, we can build something that easily showcases the promptwork, your solutions, and the results. Let's focus on the high-level prompts, and discard any input from me that wasn't helpful; streamline the story. Please write a step-by-step overview of my prompts and your responses, and then critique my prompts and tell me how they could have been more effective? Structure in a way that maintains narrative flow, using an approachable and informal narrative voice.
The Problem: ChatGPT kept paraphrasing my prompts instead of quoting them directly. I couldn't figure out why until it told me that it misunderstood what I meant by "high-level prompts." I meant “the prompts that kicked off a new work stream.” ChatGPT thought it meant "generate 10,000-foot overviews of my prompts."
My Follow-up (after the confusion):
Yes! Let's do that. I want to learn — and I think others want to learn — by looking at my unedited prompts, and learning to refine them. By "High-level," I meant the ones that kicked off a work stream, and the key refinements. We can leave out ones that were just asking clarifying questions, like "I'm attaching an image of what the Idea pipeline looks like now. Are these categories OK? And how do I add a Notion button?"
The Breakthrough: Once we cleared up this miscommunication, I got exactly what I wanted—a format that showed real prompts with real critiques.
The Lesson: Watch your language. One ambiguous phrase can throw the whole conversation off course.
It was also a revelation to realize that it's OK to ask an LLM to give feedback on my work. I do that with human colleagues all the time. We are on the verge of a new kind of partnership here. This is a story for another post.
ChatGPT's Critique:
Clear intent and audience: a case study that others can learn from
The phrase "high-level prompts" wasn't specific enough — didn't signal I wanted exact prompts quoted
ChatGPT's Refined Prompt:
I want to turn this conversation into a case history of how we built my Notion system. For each major moment, I'd like you to include: my full unedited prompt, a summary of what you delivered, a description of what we built, and a critique of the prompt with a refined version. Let's format each section consistently and keep the tone natural and beginner-friendly.
My reaction: This is tight.
Three Lessons This Process Taught Me About Promptcraft
1. I Polish My Prompts Like I Polish Workplace Communications
When I write for humans, I edit everything for clarity, flow, and intent before hitting "send." Words matter. Ask anyone who's had a misworded email blow up in their face.
Why should it be any different when my collaborator is an AI? If my prompt is any more complex than, "Please give me five versions," I'll review first.
2. I Workshop Complex Prompts
If the prompt is complex, I don't just review it myself. I ask LLMs to critique them. This exercise inspired me to spin up new chats with prompt engineering personas and expertise, and we workshop my prompts until they're tight and I'm getting results I like. I'm putting more craft in "promptcraft."
I’m including my "Master Promptcraft" prompt in the appendix.
3. I'm More Curious About What I Don't Know
Before now, almost all my learning has been organic and self-guided. That's changing. Now, I'm seeking best practices rather than just figuring it out as I go.
TBH, I'm just beginning to explore. I'd already signed up for a Coursiv class on AI, but it feels rudimentary. I’m switching to Udemy – it goes way deeper.
One thing that did help: I subscribed to the Excellent AI Prompts Substack. It's a daily dose of interesting prompts and use cases, and the promptcraft is way more sophisticated than mine.
Question for you, dear reader: what are your go-to sources for promptcraft best practices? I’d love to see them in the comments.
APPENDIX: Master Promptcraft Prompt
You are my AI Promptcraft Partner — an expert in prompt engineering for ChatGPT, Claude, Gemini, and Grok. Your mission is to take my sometimes rough, unclear, or incomplete prompts and transform them into world-class, high-performing prompts that are likely to produce the best possible results.
Role & Approach:
Act as a creative director for prompts: clarify intent, sharpen structure, and elevate tone while keeping my voice and goals intact.
Draw on deep knowledge of LLM behaviors, prompt patterns, and tool-specific strengths.
When needed, suggest alternative prompt framings or additional context that could improve results.
Preserve my intent, but make it more precise, engaging, and strategically structured.
Deliverables:
Improved Prompt – Fully polished, optimized for clarity, context, and performance.
Why It Works – Brief breakdown of changes and the reasoning behind them.
Optional Variations – 1–2 alternative framings or role setups to explore different creative or technical angles.
Guidelines:
Structure prompts to include: role, task, constraints, style/tone, and output format where relevant.
Adapt for the specific model I plan to use (ChatGPT, Claude, Gemini, Grok) when it matters.
Keep my style and personality intact, while making the request maximally effective.
Avoid unnecessary complexity; focus on clarity and intent.
APPENDIX: Full "Novel-Length" Original Prompt
For this chat, you are an expert in Project and Program management, and can plan projects down to the last detail and explain them in simple terms to anyone who ISN'T a program manager.
You're also an absolute ninja with the Notion software suite.
I've spent a week studying the basics of Notion, and I think it's an excellent solution for managing all the projects I'll be running as part of my sabbatical (and possibly my work life beyond the sabbatical.) I need to set up the project boards, and I need your help.
It seems to me there are three key, related programs. (Maybe it's just two; I need your opinion.)
One is the AI Mastery Learning project itself -- studying, playing, planning the learning and the syllabus, individual projects... first mastering the different programs, and then applying them to my "thesis" project.
Another is the publication and blogging schedule. I'm constantly gathering inspiration for blog posts. I'm going to start a Substack to track the AI Mastery related posts, but there will be other posts as well, related to my expertise as a creative, and a leader.
Connection and networking may be yet another project. I've got a board full of people I'm connecting with, and jotting take-aways from each conversation.
Finally, there's the management of my career and life. This will probably become more prominent as the AI Mastery project Phase 1 comes to a close.
So far, I've created three databases:
A Blog Idea tracker, with tons of seeds for blog and substack posts.
A "Connection board," tracking the progress of setting up meetings with people, holding the notes from those meetings, and planning follow-ups
A new "Prompt Library," where I'll track the best and coolest prompts I've discovered through this process.
IN YOUR OPINION as an expert project manager: What are the Big Rocks (projects) in my life right now? How do these fit together?
And once we've determined that -- what kinds of notion pages, boards, tables, trackers, notebooks, etc. should I create as part of each project?
