AI-Powered Document Checklists use artificial intelligence to generate draft checklists for clients, saving time while ensuring nothing gets missed.
Feature Scope
The AI checklist generator only works with tax-related documents at this time.
It is best used to request standard items for individual or business tax prep.
Non-tax scenarios (e.g., bookkeeping, payroll, advisory) are not supported yet.
The AI checklist generator is in beta, so keep an eye out for future updates and improvements!
Why it matters
AI-powered checklists help practitioners collect the right files faster during tax season prep. The tool generates draft requests for common tax-related documents, which you can edit before sending to clients.
Prompt Bank (Examples)
Here are sample prompts you can use when drafting a checklist:
“Generate a document checklist for 2025 tax preparation based on this client’s prior year submissions.”
“Draft a request for the documents this client will likely need to provide for their 2025 taxes.”
“Put together a starter list of documents this client will probably need for 2025 tax prep.”
“Give me a draft list of the docs this client is likely to need for their 2025 return.”
💡 Tip: Keep prompts short and focused on tax preparation. The AI will generate a checklist you can edit before sending.
Table of Contents
Required Setup
Plan/Permissions: Document Management License and Permissions
Enablement:
Click the Profile icon.
Select Settings.
Go to Experimental features.
Toggle on AI Document Checklist Generation.
Also toggle on Document Checklist Beta.
Create an AI-Powered Document Checklist for a Single Client
Click the Global + icon in the navigation bar.
Select Document Checklist from the menu.
In the modal, toggle Draft using AI.
Keep toggled off to create a manual checklist.
Toggle on to generate with AI.
Enter a prompt to describe the checklist (see Prompt Bank for ideas).
(Optional) Upload a file to guide AI generation (e.g., prior tax return, completed questionnaire).
You can upload a file from your computer hard drive, or select an existing file stored in the client record.
(Optional) Select a Document Checklist template if you want to apply an existing format.
Link the client.
Complete additional fields:
Assignee(s)
Client due date
Client reminder
Client-facing description (optional)
Click Create.
The checklist will take a moment to generate.
Edit and Preview an AI-Generated Checklist
Once the draft is generated, you can:
Edit the title.
Edit file upload titles and descriptions.
Use the settings icon next to each file upload slot to:
Toggle Required on/off.
Toggle the description field on/off.
Use the 3-dot icon to duplicate or delete a file upload slot.
Drag and drop file slots to reorder.
Click + Add checklist item to add another slot.
Preview includes:
Bulk Upload: Clients drag and drop multiple files.
Upload file: Upload files individually per slot.
Not applicable: Clients mark a file slot as unnecessary.
Provided elsewhere: Clients indicate they already sent a file (with comment field).
Additional attachments: Clients can add extra files at the bottom.
Send an AI-Powered Document Checklist
After reviewing, click Send.
Choose Send now or Save as draft.
If sending now, select the contacts.
A notification confirms the checklist was sent.
Send AI-Powered Document Checklists in Bulk
Go to Clients > Client List.
Select checkboxes next to the clients.
Click the 3-dot icon in the bulk actions menu.
Select Send document checklist.
In the modal, fill out checklist info and enable AI draft.
Note: Bulk checklists do not allow file uploads (since they are client-specific).
Click Create.
A notification confirms generation is in progress.
Review and Send Bulk Checklists
Once generation is complete, click the Profile icon.
Select Notifications > Unread > Document Checklist drafts.
Open the draft modal:
Select each client on the left to review/edit their checklist.
Edit titles, descriptions, required toggles, order, and slots as needed.
Click Preview to view client-facing version.
Send options:
Send to [client] one at a time.
Send all to send all drafts at once.
A notification confirms the checklists have been sent.
Track Document Checklists
Go to Work > Task List.
Filter by Task Type = Document Checklists.
(Optional) Save as a preset filter for easier access.
Note: Document Checklists can also be managed for individual clients in the Task list within the Client Record.
Summary
AI-Powered Document Checklists simplify tax document collection by generating drafts from prompts and client context. You can review, edit, and send individually or in bulk, and track all checklist tasks from the Task List.
Need help?
Contact Support or ask Penny, our AI Support Bot, for assistance.