How to Give Your AI A Fighting Chance

It’s hard to overstate how little your typical AI knows about your work when you first send it a prompt. Most AI tools start with almost no understanding of your firm, your jurisdiction, your clients, or the task you’re trying to complete.

Think of it this way: if you hired a new paralegal and told them nothing about your practice, you’d get useless generic work back. The same is true for AI.

The good news is that most AI tools give you several ways to tell the AI who you are and what you do — so you’re not starting from scratch every session.

Here are the three main layers of instructions, from broadest to most specific.

1. Account-Based Custom Instructions

Custom instructions are usually found under Settings in most AI tools. This is the 30,000-foot view of who you are and what you do. The AI reads these instructions before starting a new conversation.

Keep this section general. For example:

I am an attorney in Ohio. My practice is primarily probate and family law in Cuyahoga County. I work with small-firm tools and prefer plain-language drafts I can edit, not finished filings.

That’s enough. Don’t try to cram in every detail of your practice.

2. Project Settings

Most AI tools now let you create projects — a workspace dedicated to one matter, one client, or one ongoing task. Each project can have its own instructions describing what you are trying to accomplish.

For example:

This project is for a family law brief involving custody and visitation of two children, a brother and sister, both under 14. The opposing party is pro se. Follow Cuyahoga County local rules.

Now the AI has both the big picture — you are an Ohio family law attorney — and the specific assignment: this brief, these children, and this court. You’ll find that the quality of the first draft usually improves significantly.

3. Files

Files give the AI the raw material it needs to do useful work. You can use them in two ways.

In a regular chat, you can upload a file such as a contract, transcript, form, pleading, or letter. The AI can then review that file and answer questions about it. This is useful for one-time tasks.

Within a project, files can be added to a reusable knowledge base. You might add pleadings, templates, prior orders, client intake forms, or court-specific materials. The AI may not read every file every time, but you can refer to a file directly in your prompt, or the AI tool will often use it when the file name or context makes its relevance clear. This saves you from having to upload the same materials repeatedly.

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What Are Markdown Files?

If you are using more advanced AI tools such as Claude Code, CoWork, or Codex that can access folders on your computer, there is another useful layer: markdown files — that is, files saved with the .md extension.

A markdown file is a plain text file where you write instructions, preferences, or reference information you want the AI to have on hand. Think of it as a standing memo to the AI: here is how I work, here are the rules I follow, here is what I expect. Instead of typing the same background into every session or uploading a Word document, you save the information once in a lightweight text file, and the AI can read it whenever it’s relevant.

AI tools handle markdown especially well because the format is clean and easy to read.

Some tools automatically read a default markdown file, often named something like CLAUDE.md, whenever you work in a folder that contains it. You can also create separate markdown files for specific purposes, such as:

• brief-formatting-rules.md
• email-templates.md
• standard-intake-checklist.md
• court-specific-filing-requirements.md

You write these once, and the AI can use them repeatedly.

How To Make A Markdown File

The good news: a markdown file is just a plain text file. Notepad, which comes free with every copy of Windows, is all you need. Open Notepad, type your content, and when you save the file, change the Save as type dropdown to All Files and give it a name ending in .md — for example, brief-formatting.md. That’s the whole trick. Files ending in .md will be recognized by your AI, which will open and read them when they are relevant.

The one piece of formatting worth learning is headings. In a Word document, you’d make a heading by changing the font size or clicking a Heading 1 button. In a plain text editor like Notepad, you can’t do that, so a markdown file uses pound signs — also called hash marks — at the start of a line to mark headings.

One pound sign (#) is the biggest, top-level heading. Two (##) is a sub-heading. Three (###) is a sub-sub-heading. So a file might look like this:

# Brief Formatting Rules

## Captions Always use the full case caption from the most recent filing.

## Citations Use Bluebook format. Ohio cases first, fed next.

Headings are not just layout decoration. They matter more than you might think because the AI uses them to navigate the file.

When you ask a question about citations, the AI can jump straight to the Citations heading instead of reading the whole document and guessing what’s relevant. A well-organized markdown file with clear headings produces noticeably better answers than a wall of unbroken text.

Bonus tip: If creating the file yourself feels like a chore, just ask your AI tool to do it for you. Describe what you want:

Create a markdown file called email-templates.md with my standard responses for new client inquiries, scheduling, and fee questions .

Your AI tool will write it for you.

The Bottom Line

Context is the difference between an AI that feels like a generic chatbot and one that feels like a colleague who understands your practice.

Spend an hour setting up your custom instructions, project descriptions, and a few well-chosen files. You’ll get that time back many times over — because your AI won’t have to relearn everything each time you use it.