Stop Re-Explaining Yourself to AI: Build a Context File in 30 Questions

Every new AI conversation starts from zero. You explain your role, your company, your clients and how you like things written, and then you do it again the next day. A context file fixes that.

What a context file is

A context file, often saved as Context.md, is a short document about you and your work. It gives the AI the standing background it needs, so you can paste it in at the start of any conversation and get to the real question right away.

Let the AI interview you

The easiest way to build one is to have the AI interview you. You paste in a set of instructions, answer one question at a time, and the AI assembles the file at the end. The interview works best when the AI follows a few simple rules:

• Ask one question at a time and wait for the answer.
• Go through the categories in order and announce each one.
• Ask a follow-up when an answer is vague or thin.
• Keep questions short and conversational.
• Let the person say "skip" or "move on" at any point.

The six categories

The interview covers 30 questions across six areas:

• Who you are: your name, role, company, location and day-to-day responsibilities.
• Your work: this quarter's priorities, active projects and recurring deliverables.
• Your people and clients: who you work with, who you report to, and names or terms the AI should recognize.
• How you work: your tools, your workflow, how you make decisions and what slows you down.
• Your preferences: the tone, format and length you want, and what the AI should always or never do.
• Your goals: what success looks like in the next 6 to 12 months and what you are building toward.

When the interview is done, the AI summarizes what it heard, asks you to confirm or correct anything, and outputs a clean Context.md with a header for each category.

Keep it safe

A context file is meant to be reused, so treat it like anything else you share with an AI tool. Describe your clients and work in general terms, and keep passwords, Social Security numbers, financial account details, health information and confidential client data out of it. Use it with company-approved AI accounts, not personal ones.

Free download: Context File Interview

Our guide includes the full interview instructions and all 30 questions, ready to paste into Claude, ChatGPT or your AI tool of choice. Download the Context File Interview from our free resource library.

Want AI working this way across your team?

A context file makes one person faster. Making AI safe and useful for a whole business takes approved accounts, clear rules and the right settings. Get your free Cyber and AI Risk Score to see where your team stands.