SimpleAI is a Microsoft Word Add-in that supports every stage of contract review and drafting, all without leaving your document. It combines structured review through Playbooks with on-demand AI assistance for queries, redlines, drafting, and summaries.

But what makes SimpleAI truly different is its integration with Law Insider - a database of millions of real-world contracts. This means SimpleAI isn’t just “AI-powered.” It’s data-backed AI, anchored in how contracts are actually drafted and negotiated in practice.

How SimpleAI Works 

SimpleAI gives you a complete contract review assistant. There are two predominant ways to use SimpleAI 

1) Targeted review and edits - AI Assistant 

Use SimpleAI when you already know what you’re looking for.

• Ask specific questions about a clause or concept
• Make precise redlines or improvements to selected language
• Validate or strengthen provisions without re-reviewing the whole document

2) End-to-end contract review - Playbooks 

Use SimpleAI to run a full review against structured playbooks.

• Scan the entire agreement for issues, gaps, and deviations
• Apply internal or standard playbooks consistently
• Surface both legal and non-legal issues in one pass

SimpleAI Assistant 

Sitting alongside the contract, the SImpleAI Assistant responds in real time to questions, drafting requests, redlining instructions, and comparison tasks. It reads the full agreement, understands clause context, and produces structured, contract-aware outputs while leaving all decisions and final edits firmly with the user.

The SimpleAI Assistant supports four core contract tasks:

• Ask: Get clear, clause-aware answers to questions about the agreement, including summaries, issue spotting, and obligation mapping.
• Redline: Propose edits to strengthen, soften, align, or insert provisions—always requiring user approval before any change is applied.
• Draft: Generate new clauses, alternative language, definitions, summaries, or rewrites that match the style and terminology of the existing contract.
• Compare: Instantly compare two versions of a document to identify additions, deletions, structural changes, and shifts in legal or commercial risk.

SimpleAI Playbooks 

AI Playbooks define how contracts are reviewed. They capture your legal standards, negotiation positions, and risk tolerances as structured rules that the AI can apply consistently across agreements. They turn Legal expertise into repeatable logic, so the same issues are spotted, assessed, and handled the same way every time.

What AI Playbooks Are Designed to Do

AI Playbooks support four core functions in contract review:

1. Identify Review Issues Playbooks scan contracts to detect missing provisions, non-standard positions, and risk issues based on substance, not keywords. Rules are clause-aware and trigger based on how the agreement is actually drafted.

2. Apply Pre-Defined Legal Logic Each Playbook rule encodes a specific position or check, including:

• what to look for in the contract
• how to assess the language against your standards
• whether an issue should result in a Redline or a Red Flag action

This ensures review outcomes don’t depend on who happens to be doing the review.

3. Drive Consistent Outputs
When a rule is triggered, Playbooks can:

• insert missing protections
• revise unclear or weak drafting
• propose alternative language aligned to fallback positions
• surface guidance without editing the document

All actions remain subject to user approval.

4. Standardize Contract Review at Scale
Playbooks allow Legal teams to:

• apply consistent review logic across large volumes of contracts
• reduce variance between reviewers and teams
• embed internal policy directly into the review process
• scale without diluting legal quality

The Contract Intelligence Layer

What makes SimpleAI different is not just what it can do but what it knows. SimpleAI is powered by a Contract Intelligence Layer that combines three sources of real-world context:

• the Law Insider database
• your own contract repository
• established contract Standards

Together, these form the grounding layer behind every output, ensuring the AI is anchored in real contract practice rather than generic language or abstract rules.

Law Insider Index: Market Reality, Not Theory

Law Insider brings over a decade of clause-level contract data into the review process. Instead of relying on narrow public filings or unstructured internet sources, the AI can assess language against millions of real agreements used in practice across industries and jurisdictions.

Law Insider Index enables the AI to:

• recognise familiar and established drafting
• identify unusual or non-standard language
• surface missing or uncommon provisions
• benchmark clauses against how contracts are actually written

The result is outputs that are recognisable, credible, and grounded in market reality.

Standards: Codified Best Practice

With over 55 Playbooks grounded in real data and community consensus, Standards bring open, widely adopted contract positions directly into the review process. These are not abstract guidelines - they are concrete, clause-level standards such as oneNDA, built collaboratively by the legal community and used in real transactions.

By integrating Standards into SimpleAI, the platform can:

• anchor reviews to publicly documented, consensus-driven positions
• accelerate agreement by reducing unnecessary back-and-forth on settled issues
• provide a credible reference point when pushing back on non-standard drafting

Used together with Playbooks and the Law Insider Index, Standards allow SimpleAI to balance flexibility with consistency: standardising what should be standard, while preserving judgment where it matters.

Your Own Contracts: Internal Precedent and Policy

SimpleAI can also draw on your own contract repository - your signed agreements, templates, and negotiated outcomes.

This allows the AI to:

• align reviews with your historical positions
• reflect internal policy and risk tolerance
• draft language consistent with how your organisation contracts in practice
• reduce divergence between “policy” and precedent

Over time, this turns your contract history into a living source of intelligence.

How the Contract Intelligence Layer Works in Practice

When SimpleAI drafts, reviews, or redlines a contract, the intelligence layer provides comparative context rather than prescriptive answers.

The Assistant reads the document and identifies the relevant clauses or issues. The intelligence layer then allows users to see how that language aligns with:

• similar agreements in the broader market
• their own previously signed contracts
• community Standards that reflect established best practice

This gives lawyers immediate visibility into where the contract sits relative to real-world precedent.

What This Enables

For drafting. When the AI proposes new language, whether a clause, fallback position, or rewrite, that language is benchmarked against real precedent. Users can see that the output reflects language that has actually been used before, reducing the risk of fabricated or unrecognisable drafting.

The result is AI-generated language that is credible, familiar, and defensible rather than speculative.

For review. Instead of reviewing in a vacuum, users gain instant insight into how a clause compares:

• Is this position common or unusual?
• Is it stronger or weaker than what we usually accept?
• Does it align with community standards or diverge from them?

This context allows lawyers to assess risk and make decisions faster, without manually hunting for comparables or relying solely on memory. 

How SimpleAI Fits Into Legal Work

SimpleAI is designed to work the way lawyers already do:

• You stay in Word
• You control every edit
• Outputs are fully editable
• Follow-up questions are instant

And whereas most legal AI tools operate in isolation generating language without understanding whether it is recognisable, appropriate, or grounded in real contracts. SimpleAI’s contract intelligence layer changes that. It brings context, history, and market reality into every interaction so AI outputs are not just fast, but defensible, consistent, and commercially credible.

The goal is not to replace legal judgment, but to remove friction from review, drafting, and negotiation.

What This Manual Covers

This manual explains how to use SimpleAI’s interactive features through practical guidance, examples, and workflows, showing how they can be used individually or combined to streamline contract work end to end.