Chapter 2 · 8 min read

SimpleAI gives you four ways to work with a contract: Ask, Redline, Draft, and Compare. Each one produces a different kind of output. Choosing the right action before you type your instruction is the single most important habit to develop — it determines whether the AI understands what you're trying to do.

One question before every prompt

Before you type anything, ask yourself what you actually need right now. The answer will always land in one of four places:

• Do I need to understand something about this contract? → Ask
• Do I want to improve or fix language that already exists? → Redline
• Do I need new language that doesn't exist yet? → Draft
• Do I have two documents and need to see the differences? → Compare

Everything fits into these four categories. The rest of this chapter explains each one, shows you when to use it, and helps you spot the boundaries so you don't accidentally send the AI in the wrong direction.

Ask: Understand before you act

What it does

Ask reads the contract and answers your question. It summarizes, explains, identifies risks, spots gaps, maps obligations, and flags inconsistencies. It never edits the document. Its only job is to help you understand what you're looking at.

Use Ask when you want to

• Summarize a clause or the whole agreement
• Find where something is covered in the contract
• Spot risks or issues
• Map obligations by party
• Identify what's missing
• Check how language compares to market norms

Don't use Ask to

Edit the document, propose changes, or create new language. If you want to change something, that's Redline or Draft.

Example prompts

     "What are the top three issues in this indemnity clause?"

     "Summarize all obligations on the Supplier in plain English."

💡 Tip: Ask before you act. Running Ask before Redline or Draft is the most reliable way to get clean output. Understanding the problem first means you can give the AI a precise instruction instead of a vague one.

Redline: Improve what's already there

What it does

Redline proposes changes to language that already exists in the document. It targets a clause, modifies it, and inserts the result as a Word tracked change - exactly as a human reviewer would mark up a contract. You review the proposed change and decide whether to apply it, reject it, or ask for a revision.

Use Redline when you want to

• Strengthen or soften a clause
• Add a missing protection to existing language
• Fix an inconsistency or ambiguity
• Align language with defined terms elsewhere in the contract
• Make an obligation mutual
• Correct a cross-reference error

Don't use Redline to

Create a completely new clause (use Draft instead), or understand what a clause means (use Ask first).

Example prompts

     "Make this indemnity mutual."

     "Add a 10 business day cure period before default triggers termination."

📝 Redline vs Draft - the key distinction. Redline modifies existing text. Draft creates new text. If the clause already exists and needs improvement, use Redline. If the contract is completely silent on the topic, use Draft. When in doubt: if there's something to edit, Redline. If there's nothing to edit, Draft.

Draft: Create what isn't there yet

What it does

Draft generates new contract language. It creates clauses, definitions, alternative versions, fallback positions, schedules, and rewrites, adapted to the style, terminology, and structure of your existing document. You review the proposed language and insert it where needed.

Use Draft when you want to

• Insert a clause that doesn't exist in the document
• Create alternative versions of a clause for negotiation
• Add a new definition
• Rewrite a clause entirely from scratch
• Draft a schedule, exhibit, or annex

Don't use Draft to

Make line-by-line fixes to existing text (use Redline), or understand what a clause means (use Ask).

Example prompts

     "Draft a mutual NDA clause covering all business, technical, and commercial information."

     "Give me a supplier-friendly liability cap clause"

Compare: See exactly what changed

What it does

Compare takes two documents and shows you the differences. It identifies additions, deletions, modified obligations, shifted risk allocation, and hidden edits buried inside long paragraphs. Compare doesn't analyse or rewrite - its only job is to surface what changed between the two versions.

Use Compare when you want to

• Review a counterparty's revised draft
• See what was accepted or reversed after you sent redlines
• Spot hidden edits in long paragraphs
• Check that a contract reflects what was agreed in a term sheet
• Validate negotiation notes against the final draft

You can upload any file format when you use Compare.

Don't use Compare for

Single documents. Compare requires two documents. For analysis of one document, use Ask.

Example prompt

     After running Compare, follow up with Ask: "Which of these changes increase our commercial risk?"

Quick reference: task → action

One action per prompt

Each prompt should contain exactly one action. When you combine instructions - "summarize this and redline it to cap liability at 12 months" - the AI has to guess which instruction matters most. The output becomes unpredictable.

❌ Don't do this: "Summarize the indemnity clause and redline it to make it mutual and also give me an alternative version."

✅ Do this instead: Step 1 - Ask: "What's the issue with this indemnity?" Step 2 - Redline: "Make the indemnity mutual."

The second approach takes an extra 30 seconds and produces dramatically cleaner output. The AI knows exactly what to do at each step because you've removed the ambiguity.

⚠️ Watch out for this. The most common mistake is asking for an explanation while in Redline mode. If you're in Redline and ask "explain this clause," the AI tries to produce an edit, not an explanation. Switch to Ask for any question. Switch to Redline only when you want a tracked change.

Sequencing actions for better results

The four actions can be used in sequence. Running Ask before Redline or Compare before Ask, consistently produces better output than any single action in isolation. These are the three sequences that come up most often in practice.

Sequence 1 - Ask → Redline: diagnose then fix

Ask: "What's weak about this limitation of liability clause?" Redline: "Cap liability at 12 months' fees and add a carve-out for gross negligence."

Sequence 2 - Ask → Draft: identify gaps then fill them

Ask: "What protections are missing for the Customer?" Draft: "Draft a data security clause covering industry-standard obligations."

Sequence 3 - Compare → Ask → Redline: detect changes then respond

Compare v3 to v2. Ask: "Which of these changes weaken our position?" Redline: "Restore the liability cap to the previous version."

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The chapters that follow go deep on each individual action. If you're already clear on which action you need, skip directly to that chapter. If you're still unsure, come back to the decision framework at the top of this one.

Next chapter → Ask Mode: Getting Answers From Any Contract

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