Ask is the AI Assistant's analytical engine. It helps you understand a contract before you touch anything. You can ask about obligations, risks, definitions, gaps, inconsistencies - anything you'd normally ask a colleague to look up or a junior lawyer to summarize. Ask never edits the document. It interprets, explains, maps, and highlights. Everything that happens after - every redline, every draft - works better when you've used Ask first.

How to use Ask

1. Open your contract in Word and launch the SimpleAI sidebar
2. Select Ask from the action selector
3. Type your question or instruction
4. Hit send

You don't need to highlight anything. SimpleAI reads the full document automatically. If you want the AI to focus on a specific clause, highlight it before submitting, but for broad questions, leave the selection empty and let it read the whole agreement.

What Ask is built for

Ask handles four categories of work better than any other action.

Understanding the contract

The most common use. Before you start editing anything, Ask gives you a clear picture of what you're working with.

     "Summarize the payment terms in plain English."

     "Where are the termination rights located?"

     "List all Supplier obligations."

     "Does this clause contradict anything else in the agreement?"

Preparing for review

Use Ask as pre-work before you start redlining. It gives you a precise map of where to focus instead of reading the whole document linearly.

     "Which clauses need the most attention and why?"

     "Is anything missing compared to a typical SaaS agreement?"

     "What protections are missing based on typical market practice?"

Supporting negotiation

Ask becomes a second chair during live negotiations. Paste in counterparty language, test proposed changes, and generate talking points in real time.

     "What would be the impact of accepting their proposed limitation of liability clause?"

     "If I can't get a mutual indemnity, what's a commercially reasonable fallback?"

     "Give me negotiation talking points for the SLA section - strict, balanced, and friendly versions."

Communicating after review

Once you've finished redlining, Ask turns your analysis into something you can share. It drafts internal summaries, stakeholder updates, and plain-English explanations of complex clauses.

     "Summarize the key risks and proposed changes for the commercial team."

     "Explain in plain English why each redline was proposed."

     "Give me a list of decisions the business needs to make before we send this back."

Prompts that work well in practice

The prompts below are ready to use. They're grouped by the stage of review you're in.

Before you start editing

     "Give me a high-level summary of this agreement."

     "What are the five clauses I should pay most attention to and why?"

     "Identify the key risks to the Customer in this agreement."

     "What obligations fall on the Supplier vs the Customer? Summarize them separately."

     "List all defined terms that are not actually defined."

     "Map all references to 'Service Levels' across the contract."

During review

     "Is this limitation of liability reciprocal or one-sided?"

     "Summarize our confidentiality obligations and their duration."

     "What's the process for dispute resolution under this agreement?"

     "Are there any personal data transfer restrictions in this contract?"

After editing

     "Will this new clause conflict with anything else in the agreement?"

     "Does this change affect the definition of 'Fees'?"

     "Does this interact with the SLA section? How?"

During negotiations

     "What risks does their proposed exclusivity right create for us?"

     "Is this clause typical? What's missing? Where might it be risky?"

     "Does their proposed wording contradict anything else in the agreement?"

     "Summarize our position on the IP clause in a way I can send to the counterparty."

How to get better output from Ask

Be specific. The more precise your question, the more useful the answer.

     "Explain this clause" works.

     "Explain what each sentence of this clause does and flag any ambiguity" works better.

Ask follow-up questions. Treat it like a conversation. If the first answer gives you 80% of what you need, ask the follow-up directly instead of rephrasing the original question.

Ask for structure when you need it. If you want the output in a particular format, say so.

     "Summarize this in bullet points."

     "Give me a risk map by clause."

     "Explain this in plain English for a non-lawyer."

Use Ask for second opinions. It's not just for summarizing — it's for pressure-testing your own thinking.

     "Is this clause typical?"

     "What would a Supplier push back on here?"

     "What's the hidden risk in this provision?"

💡 The best Ask prompts start with a clear goal. Before you type, ask yourself: do I want a summary, a risk assessment, a gap analysis, or a specific answer? Each of those needs a slightly different prompt, and naming the goal upfront produces much cleaner output.

What Ask won't do

Ask will not edit the document. If you type an editing instruction - "fix this clause," "make this mutual," "add a cure period" while in Ask mode, you'll get an explanation or analysis in return, not a change. That's Redline's job.

This is the most common source of frustration for new users, and it's easy to fix: check the action selector before you submit. If you want a change, switch to Redline or Draft first.

⚠️ Ask analyzes. It does not act. If you find yourself wanting to change something based on what Ask tells you, that's the signal to switch modes.

Ask as part of a workflow

Ask produces the most value when it's the first step in a sequence, not a standalone action.

Ask → Redline

Understand the problem, then fix it precisely. Once Ask has identified the issue, highlight the relevant clause in your document, switch to Redline, and give your instruction.

Ask: "What's the issue with this indemnity clause?"

Highlight the indemnity clause, switch to Redline: "Make this clause mutual and add a carve-out for gross negligence."

Ask → Draft

Identify what's missing, then create it.

Ask: "What protections are missing for the Customer?"

Draft: "Draft a data security clause with industry-standard obligations."

Ask → Explain → Communicate

Understand the clause, then turn it into something shareable.

Ask: "Summarize the key commercial risks in this agreement."

Ask: "Rewrite that summary in non-legal language for a product manager."

The pattern is the same every time: use Ask to get clarity, then act on that clarity with the right tool.

Next chapter → Redline: Making Targeted Edits

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