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Ask Tiff

Your AI legal assistant built directly into ProPlaintiff.ai. Tiff works alongside your cases, files, contacts, and other case data to help you research, analyze, draft, organize, and complete legal work faster. Ask Tiff anything & see what she can do.

Ask Tiff Full Walk-Through

Ask Tiff Video Transcript

The AI paralegal serves as your go-to assistant for drafting, research, and document analysis within ProPlaintiff. From the home screen, you’ll find a familiar chat interface where you can enter prompts or choose from suggested requests. You can ask it to create motions, subpoenas, batch draft interrogatories, or draft mediation letters. It also supports document uploads, allowing you to attach files such as PDFs from your computer or connected apps like Google Drive. By using @mentions, you can reference specific cases and prompt the AI to return detailed case information instantly.

The AI paralegal is especially effective for starting new cases, editing existing ones, drafting legal documents using case data, conducting legal research through a case law database, and managing tasks, calendar events, time entries, and expenses. With built-in agentic AI capabilities, it can also handle more complex, multi-step tasks. For example, you can prompt it to draft a demand letter for an existing case and suggest an appropriate demand amount. The AI will execute a sequence of actions, which you can monitor in the chat log, and once complete, you can review its work, ask follow-up questions, or request revisions in real time.

To get the best results, it’s important to write clear and specific prompts. Providing context—such as who the task is for, what you need, and why—helps the AI generate more accurate outputs. Using @mentions to reference cases and assigning tasks to team members further improves precision. Be explicit about the format, style, and jurisdictional requirements of the document you need. If you want content written in a particular tone or for a specific audience, clearly define those characteristics in your prompt. By refining how you communicate with the AI paralegal, you can significantly improve the quality and usefulness of its responses.

Where to Find Ask Tiff

  1. Log in to ProPlaintiff.ai

  2. Open the main navigation panel on the left side of the screen

  3. Select Ask Tiff

The Ask Tiff workspace gives you a central place to work with Tiff, access previous threads, reference cases, upload files, and submit new requests.

Quick Access to Tiff

Tiff is also available from the Ask Tiff button in the lower-right corner throughout ProPlaintiff.ai.

This allows you to ask Tiff a question or get assistance without leaving the page you're currently working on.

Use it while reviewing a case, working with files, managing your calendar, or completing other tasks throughout the platform.

What Can Tiff Do?

Tiff is designed to assist with work across your cases rather than perform only one specific task.

Here are just a few things you can ask Tiff to do:

  • Answer questions about a case or its files

  • Review and summarize documents

  • Research case law and legal issues

  • Draft legal documents and correspondence

  • Create Demand Letters and Medical Chronologies

  • Analyze case information

  • Help identify important dates or information

  • Create and manage case information

  • Work with uploaded files and images

  • Save generated documents directly to Case Files

These are only examples. If you're not sure whether Tiff can help with something, ask her.

Work Within a Case

Tiff can work with information already stored in ProPlaintiff.ai, allowing her to provide assistance based on the context of your case.

Use the @ symbol to reference a case in your request.

Example:

“Summarize the medical treatment for @Brown v Smith.”

Referencing the case gives Tiff access to the relevant case context and files so you don't have to repeatedly provide the same information.

Organize Your Work with Threads

Threads allow you to organize your conversations with Tiff and return to them later.

Instead of starting a new conversation every time you have a question, you can create a dedicated thread for a case, topic, or project and continue working from the same conversation.

For example, you might create a thread for a specific case and use it to:

  • Ask questions about the case

  • Review medical records

  • Discuss liability

  • Draft correspondence

  • Analyze damages

  • Generate documents

  • Continue previous research

As you continue working within the thread, Tiff can use the conversation's existing context to better understand what you're working on. This allows you to build on previous messages instead of starting over with every request.

Create Threads Around Your Workflow

Threads don't have to be limited to individual cases. You can organize them in whatever way works best for your firm.

You might create threads for:

  • Individual cases

  • Legal research

  • Document drafting

  • Medical record review

  • Settlement preparation

  • Ongoing case strategy

Keeping related work in the same thread makes it easier to return later and continue where you left off.

💡 Pro Tip: Create a dedicated thread for complex or active cases. As you continue asking questions and working through the case in the same thread, Tiff has more context to assist with future requests.

Upload Files and Images

You can provide files directly to Tiff when additional information is needed for your request.

Tiff can use uploaded documents and images to help:

  • Summarize information

  • Locate important details

  • Answer questions

  • Analyze content

  • Incorporate information into generated documents

You can then continue asking follow-up questions about the information without starting a new conversation.

Generate and Save Documents

Tiff can help create legal work product using your case information, files, and instructions.

Depending on what you need, this may include Demand Letters, Medical Chronologies, Pleadings, Communications, and other legal documents.

For more robust, structured AI-generated documents, use the dedicated Tiff Generations tools located in the left navigation:

  • Pleadings

  • Communications

  • Video Analysis

  • Demand Letter

  • Medical Chronology

These tools provide a guided generation process designed specifically for each type of work product, giving Tiff additional structure and context to produce more comprehensive results.

Once a document has been generated, you can save it directly to the appropriate Case Files, keeping the finished work product connected to the case without having to download and manually re-upload it.

💡 Pro Tip: Use Ask Tiff for conversational drafting, questions, research, and quick assistance. When you need a more comprehensive legal document, use the appropriate tool under Tiff Generations.

Paralegal Prompts

Paralegal Prompts give your team one-click access to frequently used Ask Tiff requests.

Each prompt includes:

  • A Chip Label, which is the title displayed on the Ask Tiff page

  • AI instructions that tell Tiff exactly what to do when the prompt is selected

Examples might include:

  • Demand Letter

  • Letter of Representation

  • Last Date of Service

  • Create a New Case

  • Lien Reduction

When a user selects one of these prompts, the saved instructions are inserted into the Ask Tiff composer so Tiff knows how to handle the request.

Creating Paralegal Prompts

You can create Paralegal Prompts in two places.

Option 1: From Settings

  1. Open Settings.

  2. Under the Organization section, select Paralegal Prompts.

  3. Click Add Prompt.

  4. Enter the Chip Label you want users to see.

  5. Enter the AI instructions describing what Tiff should do when the prompt is selected.

  6. Click Add Prompt.

Custom prompts appear before the standard ProPlaintiff prompts.

Team members can see up to four prompts directly below the Ask Tiff composer, with additional prompts available from the browse menu.

You can also drag and drop your custom prompts in Settings to control the order in which they appear. Hover over the 6 dots and move in the desired order you would like to see on the Ask Tiff page.

Option 2: From Ask Tiff

You can also create a new prompt without leaving the Ask Tiff page.

  1. Click the + next to the prompts below the Ask Tiff composer.

  2. Select Add New Prompt.

  3. Enter your Chip Label.

  4. Enter instructions explaining what Tiff should do when the prompt is clicked.

  5. Click Add Prompt.

The new prompt will then become available from the Ask Tiff composer.

Writing Good Prompt Instructions

The instructions should clearly tell Tiff what you want her to do when someone selects the prompt.

For example:

Chip Label:
​Last Date of Service

AI Instructions:
​Review the case files for the mentioned case and identify the client's most recent date of medical service. Provide the provider name and source document when available.

Or:

Chip Label:
​Lien Reduction

AI Instructions:
​Draft a lien reduction letter for the mentioned case using the available case details, lien information, settlement information, and supporting documents.

The more specific the instructions are, the more predictable and useful the prompt will be.

💡 Pro Tip: Create Paralegal Prompts for tasks your team performs repeatedly. This reduces repetitive typing and helps everyone use consistent instructions when working with Tiff.

How to Ask Tiff

Working with Tiff is conversational. You don't need to learn special commands or create a perfect prompt before getting started.

  1. Tell Tiff what you want to accomplish.

  2. Reference the appropriate case with @ when needed.

  3. Add relevant files or additional context.

  4. Submit your request.

  5. Continue the conversation with follow-up questions or instructions.

You can ask Tiff to revise, expand, shorten, explain, or approach the task differently until you have the result you need.

Best Practices

  • Reference the appropriate case when your request involves case-specific information.

  • Keep related work together in Threads so you can build on previous conversations.

  • Provide clear instructions when you have specific requirements for tone, structure, or output.

  • Upload relevant supporting documents when they aren't already available in the case.

  • Ask follow-up questions instead of starting over when you want to refine a result.

  • Review AI-generated work product before final use.

Key Takeaway

Tiff is your AI legal assistant inside ProPlaintiff.ai. She can work alongside your cases and files to help research, analyze, draft, organize, and complete everyday legal work.

Use Threads to build ongoing context, reference cases when you need case-specific assistance, and save completed documents directly to Case Files.

Not sure where to start? Ask Tiff anything and see what happens.

Need Help?

👉 Check out our YouTube video - ProPlaintiff.ai V3 Tutorial Walkthrough

If you need additional assistance, please don’t hesitate to reach out to our support team via chat or email us at cx@proplaintiff.ai. We're here to help!

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