After one of my workshops in August, I told the room to go home and create context documents.
The idea is straightforward. Instead of re-explaining yourself every time you open a new AI chat, you build a set of reusable files — your communication style, your business priorities, how you like decisions laid out. Load them into any AI tool, and the outputs get noticeably better. Less correcting. Less re-explaining. The AI actually knows you.
Most people heard this and nodded. A few followed through.
One of them came back a week later and told me he had completed all six of his.
But he had not written a single word.
The Blank Page Problem Nobody Talks About
Writing a context document sounds easy on paper. “Just describe yourself. Your work style. Your priorities. Your communication preferences.”
But sit down to actually do it and most people freeze. What do I even include? Where do I start? How much detail is enough?
It is the blank page problem. And it kills a lot of otherwise good intentions.
My client Evan ran into the same wall. He has been using Airtable for over a decade, so he understood the idea of structured information — he just could not figure out how to get it out of his head and into a document.
So he flipped the approach.
Dialoguing Instead of Writing
Instead of writing to the AI, Evan let the AI ask him questions.
He opened a chat and typed something like: “I want to create a context document about how I work. What do you need to know to give me consistently good outputs?”
The AI asked him questions. He answered them out loud using Whisperflow (a voice dictation tool he picked up from the workshop). No typing. No blank page. Just a conversation.
By the end of one session, he had six context documents. Communication style. Decision-making patterns. Business priorities. Weekly rhythms. How he handles conflict.
And one that surprised even him.
The Life Philosophy Context Doc
The last one Evan built was what he called his “personal philosophy context.”
What does he actually believe? What does he optimize for in his life and work? What would he never sacrifice, no matter the upside?
He said it felt more like a therapy session than a work task. Cathartic was the word he used.
I have thought about that a lot since he told me. There is something about the AI asking you questions — good, probing ones — that surfaces things writing alone does not. When you have to write, you edit yourself. When you are answering questions out loud, you are just thinking.
That is the real unlock here. Voice removes the filter that writing adds.
Why This Works (and Why Most People Are Still Doing It Wrong)
When I teach AI workflows, I talk a lot about context files as reusable assets. A good context file is like a well-written brief that you only have to create once and then load everywhere. The investment in building it pays off across every future interaction.
But there is a gap between understanding that idea and actually sitting down to build the files.
The interview method closes that gap. It turns “write a document about yourself” (hard, undefined, blank-page) into “answer these specific questions” (easy, concrete, conversational).
And here is the part that matters: voice gives you better raw material. I have been using Whisperflow for most of my own prompting. When you type, you edit as you go. When you talk, you are less filtered. The thinking is more honest, more complete. The AI picks up on that and gives you better outputs to work with.
How to Try This Today
You do not need special software. Any AI tool works.
Open a chat with ChatGPT, Claude, or Gemini and say something like:
“I want to build a context document about my work style and communication preferences. Please interview me — ask me whatever you would need to know to give me consistently useful outputs.”
Then answer the questions. Out loud if you can (Whisperflow or your phone dictation works great). In text if that is easier.
When the conversation feels complete, ask the AI to synthesize everything into a clean context document. Save it. You now have a reusable asset you can load into any workflow.
Do this for your communication style first. Then your business priorities. Then your decision-making patterns. You will have a solid set in a few sessions.
And if you want to go deep like Evan did… ask the AI to help you build one for your personal philosophy too.
You might be surprised what comes up.
Want to go deeper on context docs and AI workflows? Check out the Productivity Academy — it includes a full module on building your AI context library.
