Asking Questions About Your Document with Sidebar in Microsoft Word

Last updated: November 9, 2026

Sidebar is available inside DraftMate in Microsoft Word for all Sidebar customers. Ask questions about the document you have open, whether it is a file on your computer or a contract you opened from SpotDraft, and get answers without leaving Word.

Use case:

Meet Elena. Elena is commercial counsel at a 300-person logistics company in Rotterdam. She negotiates in Word, so checking a renewal date in a 60-page master agreement used to mean uploading the contract into a browser tab and pasting the answer back. Now she asks Sidebar inside Word and gets the dates back in one reply.

Before you start

Things to know

  • Sidebar in Word answers questions about your documents. It does not yet edit, redline, or comment on the document from the panel. These capabilities are coming in later releases.

Opening Sidebar in Word

  1. In Word, open a file from your computer, or open a contract from SpotDraft and hit "Edit in Microsoft Word".

  2. On the Home tab, click DraftMate to open the add-in.

  3. On the DraftMate home screen, click AI Assistant.

You don't need to sign in again. If you are signed in to DraftMate, you are signed in to AI Assistant.

The panel opens with suggested prompts such as Review the selected clause, Flag unusual terms, Check undefined terms, and Find the termination clause. Click Shuffle Suggestions to see others.

Asking about the open document

Sidebar knows it is running in Word and which document is open. Ask "What am I looking at?" and it names the document and suggests what to ask next, such as a summary of key terms. For a contract opened from SpotDraft, Sidebar recognizes it as that SpotDraft contract and answers questions about it the same way it does for a file on your computer.

When you ask a question, Sidebar searches the document and reads only the passages that answer it. A question about a clause near the end of a long agreement is answered without reading the whole document from the top first, and the search covers the full document regardless of its length.

You can also ask Sidebar to find a specific line or clause. It locates the text wherever it appears, including near the end of a long document, and summarizes it.

Sidebar reads the document as it is in Word at the moment you ask. If you changed the text since your last question, Sidebar is told what changed, and the next answer uses the current version.

Sidebar can also draw on your organization's Knowledge Hubs when it answers.

Citations

When Sidebar answers from your document, it underlines the parts of its answer that come from a specific place in the document, such as a section reference. Click the underlined text to jump to that part of the document in Word.

Citations work for documents opened in Microsoft Word. When these chats are opened in another surface (CLM or the Sidebar web app), these citations will not work

Asking about tracked changes

Ask Sidebar about the tracked changes in your document, for example "What changes were tracked in this document?" Sidebar can read tracked changes across the whole document or only in the text you have selected. For each change it reports the type, the text, the author, and the date.

If a document has a large number of tracked changes, Sidebar reads as many as it can and tells you how many it covered out of the total. If your version of Word does not support reading tracked changes, Sidebar tells you so.

Resizing the task pane

Sidebar needs a minimum width to display properly. If you drag the Word task pane narrower than 320 pixels, a message appears over the panel: Expand the window to get a better experience. Widen the task pane to continue. Your conversation stays in place.

What you can ask Sidebar in Word

Ask in plain language. These are the main kinds of questions, with examples.

Understand the document

  • What am I looking at?

  • Summarize this agreement in plain language.

  • Who are the parties, and what is each party responsible for?

  • What is the purpose and scope of this contract?

Find a clause or specific text

  • Find the termination clause.

  • Where does this document mention data protection?

  • Find the paragraph that starts with “The Supplier shall”.

  • Which section covers payment terms?

Pull out key terms, dates and numbers

  • What is the effective date, term, and renewal date?

  • What is the notice period for termination?

  • List all payment amounts and due dates.

  • What is the governing law and jurisdiction?

Explain a clause

  • Explain the selected clause in plain language.

  • What does “Confidential Information” mean in this agreement?

  • What are my obligations under this section?

  • What happens if either party breaches this clause?

Review and assess risk

  • Review the selected clause.

  • Flag unusual or one-sided terms.

  • What are the biggest risks for us in this contract?

  • Is the limitation of liability mutual?

Check completeness and consistency

  • Check for undefined terms.

  • Are there any defined terms that are never used?

  • Do the section cross-references point to the right clauses?

  • Is anything commonly expected in this type of agreement missing?

Ask about tracked changes

  • What changes were tracked in this document?

  • Which changes did a particular reviewer make?

  • Summarize the tracked changes in the selected section.

Ask about your latest edits

  • What did I change since my last question?

  • Does the updated clause still conflict with the termination section?

Draw on your organization’s knowledge

  • Questions that use content from your Knowledge Hubs, for example how a clause compares with your organization’s standard positions.