How to Upload Files So Your AI Assistant Works Properly

By default all AI assistants come with knowledge to answer the typical questions users may have while navigating the member portal. You can add more specific information related to your organization and its rules or anything that may assist your members and reduce the questions you receive from them.  

Your AI support assistant can only give good answers if it has clear, well-organized information to learn from. This guide explains what files to upload, how to prepare them, and what to avoid, in simple terms.

You do not need to be technical to follow these steps.

1. What Kind of Files Should I Upload?

The best files are ones that contain written explanations, just like help articles or instructions you would send to a person.

Good File Types

These work best:

• PDF documents (that you can highlight and copy text from)

• Word documents

• Simple text documents

• Web pages or help articles

If you can read the text, the AI can too.

Files to Avoid

Please avoid uploading:

• Screenshots or images of text

• Scanned documents

• PowerPoint slides with very little writing

• Files that are mostly tables with no explanations

If your information lives in one of these formats, rewrite it as a short document first.

2. Keep Each File Focused on One Topic

Each file should explain one thing.

Good Examples

• “How do I renew my membership”

• “Where can I find my invoices”

• “How do I update my contact details”

Not Recommended

• One large document that explains everything

• Notes that jump between unrelated topics

Clear, focused files help the AI give better answers.

3. Write Like You’re Explaining to a New Person

Pretend you’re explaining something to someone who has never used your system before.

Helpful Writing Style

• Use simple sentences

• Explain steps in order

• Avoid abbreviations unless you explain them

• Say what to do and what to expect

Example:

If your contacts do not appear after an import, check that the membership name in your file exactly matches the name in the system. Even small spelling differences can cause issues.

4. Use Headings and Short Sections

This makes it easier for the AI to find the right answer.

Good Structure

• Clear titles

• Short paragraphs

• Bullet points

• Step-by-step instructions

Avoid long blocks of text with no breaks.

5. Do Not Upload Private or Sensitive Information

Your uploads are for help and instructions only.

Please do not include:

• Passwords

• Credit card numbers

• Personal identification numbers

• Private customer information

If something shouldn’t be shared publicly, don’t upload it.

6. Make Sure the Information Is Current

Out-of-date instructions can cause confusion.

Before uploading:

• Remove old or incorrect steps

• Update anything that has changed

• Add a note at the top like:

“Last updated: March 2025”

7. Give Files Clear Names

Clear names help both you and the AI understand what each file is about.

Good File Names

• “Creating a membership”

• “Event setup guide”

• “Common problems with data imports”

Avoid vague names like:

• “Notes”

• “Instructions”

• “Final version”

8. Test the AI After Uploading

Once your files are uploaded, try asking the AI real questions like:

• “How do I set this up?”

• “Why isn’t this working?”

• “What should I do next?”

If the answer isn’t helpful, the information may need to be clearer or broken into smaller files.

9. Improve Over Time

It’s normal to update your files as you go.

If the AI gives a bad or incomplete answer:

1. Update or improve the file

2. Re-upload it

3. Try again

Each improvement makes the AI smarter.

Quick Checklist Before Uploading

✔ Is this written in plain language?
✔ Does the file cover one topic?
✔ Can someone new understand it?
✔ Is the information up to date?
✔ Does it avoid private or sensitive details?

If yes — it’s ready to upload.