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Overview of Ask AI Sidekick (AI Sidekick Chat)

Your in-the-flow research librarian—ask a question, get an accurate, cited answer, without leaving your workflow.


1. What is Ask AI Sidekick?

Ask AI Sidekick (also known as AI Sidekick Chat) is an intelligent, in-the-flow enablement assistant designed to provide instant, accurate answers and guidance directly within the applications you use daily. It functions like a research librarian for your company's internal knowledge.

  • Instant Answers: Ask questions directly in the chat sidebar, and the AI will synthesize a concise, accurate response based exclusively on your company's vetted internal content (Speks and files).
  • Grounded in Trust: It uses a Retrieval-Augmented Generation (RAG) pipeline to ensure answers are derived only from your internal materials, preventing the use of unverified external data.
  • Permission-Aware: The system strictly respects your existing user permissions; it will never surface a document or answer that you are not authorized to view.
  • Actionable & Cited: Every response includes source citations, so you can verify the information and explore the original source materials further.
AI Sidekick chat.gif

2. How do I use Ask AI Sidekick?

Type your question into the chat box in the Sidekick sidebar (or pop it out into a floating window). Unlike Content Recommendations, chat is available on any page while the extension is active — it isn't limited to a specific set of apps.

You can also use quick commands:

  • /search [keywords] — search your Spekit content by keyword
  • /google [query] — search the web (only available if your admin has turned this on)
  • /help — get tips for getting better answers

Each response shows its sources, and you can copy a response or give a thumbs up/down to help improve future answers. Questions are limited to 1,700 characters, and the conversation continues across multiple follow-up questions until you navigate away or close the tab.


3. What can Ask AI Sidekick help me do?

  • Get instant answers to sales, product, and process questions without searching or waiting on a teammate.
  • Draft content like follow-up emails or messaging on the fly.
  • Find specific content by asking directly or using /search.
  • Get external context (competitor info, market news) via /google, if enabled for your org.

4. What are the limitations of Ask AI Sidekick?

  • Ask AI Sidekick is currently in Beta, and AI may occasionally produce inaccurate results.
  • It answers only from your company's internal content by default — it won't access the open web unless your admin enables /google.
  • It can draft and recommend content, but can't take actions in other systems (e.g., it can't attach a file or send an email for you).
  • Conversations aren't saved long-term — navigating to a new page, refreshing, or closing the tab starts a fresh conversation.
  • Currently available in the Chrome extension only; not yet available in the Outlook add-in.
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