How to generate documents in monday.com using PDF Maker AI Skill?

PDF Maker now supports document generation through monday Sidekick. This means you can select a template and generate a PDF for a monday.com item directly through chat.

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Instead of opening PDF Maker, choosing a template manually, and running the document from a separate screen, you can ask Sidekick to do it for you. Sidekick will show the available PDF Maker templates, ask which one you want to use, request approval when needed, and generate the document into your configured output column.

This is useful for teams that create invoices, quotes, contracts, purchase orders, certificates, reports, or any document that already uses monday.com item data.
Good to know
Before using the AI Skill, create your PDF Maker template and configure the automation settings once. After that, users can generate documents from the Sidekick chat.

Before you start

PDF Maker must be installed on your monday.com account.

You should already have at least one PDF Maker template created for the board.
The template should be mapped to the monday.com columns you want to use in the document.
A file/output column should be selected in PDF Maker automation settings.
monday Sidekick should be available in your workspace.
The PDF Maker | Document Generate tool should be enabled inside Sidekick.
Recommended prompt

Use the PDF Maker tool to show available templates for this board. Then generate a PDF for this item using the selected template.

Prompt variants

Show available PDF Maker templates for this board.

Generate a PDF for this item using Invoice Template 2026.
Create the invoice PDF for this item and save it to the configured file column.
Step 1: Select Automate from the template menu

Open PDF Maker inside your monday.com board. Go to Templates, find the template you want to use, click the three-dot menu, and select Automate.

Step 2: Configure and save the document delivery settings

Choose where the generated document should be saved. Select the

output/file column, choose whether the PDF should also be attached to the Updates feed, set a custom document name if needed, and click Save & Exit.
Step 3: Select the item and open monday Sidekick

Go back to your monday.com board and select the item you want to generate a PDF for. Open the item view and click the Sidekick icon at the bottom right.

Step 4: Enable the PDF Maker Document Generate tool

Inside Sidekick, click the plus icon. Go to Manage tools and turn on PDF Maker | Document Generate.

Step 5: Ask Sidekick to use PDF Maker for document generation

Write a clear prompt asking Sidekick to use PDF Maker, show the available templates, and generate the document for the selected item.

Step 6: Approve access when Sidekick asks for permission

When Sidekick asks for permission to use boardId, review the details and click Approve.

Step 7: Choose the template from the list

Sidekick will show the PDF Maker templates available for that board. Reply with the template name or number you want to use.

Step 8: Approve the generation action

Sidekick may ask for approval again before generating the document. Review the action and click Approve.

Step 9: Confirm the success response

Once the document is generated, Sidekick will show a success message with the item, board, and template details.

Step 10: Find the generated file in your configured output column

Return to the board and check the output/file column you selected in PDF Maker. The generated PDF should be attached there.

FAQ

Can I choose the template through chat?

Yes. Sidekick can display the available PDF Maker templates and you can reply with the template name or number.


Where does the generated PDF go?
It is saved in the file/output column selected in the PDF Maker automation settings.


Can this use subitem data?
Yes, as long as your PDF Maker template is already configured to use the item and subitem data you need.


Do users need to configure the template every time?
No. The template and automation settings should be configured once. After that, users can generate documents through Sidekick.
Final note
PDF Maker AI Skill is built for teams that want document generation to feel natural inside monday.com. Pick the item, ask Sidekick, approve the action, and your PDF is generated into the right column.

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