Ask Chiefy about your inbox and calendar
Ask Chiefy is the chat where you talk to Chiefy in plain language. Ask it to find an email, explain a thread, check what’s on your calendar, or take an action like archiving or labeling — and it answers using your real inbox and, when connected, your calendar.
Ask Chiefy is the assistant chat. Instead of digging through your inbox yourself, you describe what you want and Chiefy does the work — finding the right messages, reading them, and answering in context. It keeps track of the conversation, so you can ask a follow-up without repeating yourself.
Where to find it
Ask Chiefy lives in two places, and it’s the same assistant in both:
- In the Chiefy side panel next to Gmail, opened from the extension.
- In the Chiefy web app, where the chat opens as a panel you can dock to the side or pop out.
You just type a message and send. Chiefy works through whatever you ask and replies in the chat.
What you can ask
Ask Chiefy in your own words — there’s no command syntax to learn. Common things to ask:
- Find an email. “Where’s the invoice from the venue last month?” or “Show me everything from Maria about the August booking.”
- Understand a thread. “What’s the latest on this thread, and what do they need from me?” Chiefy reads the messages and gives you the short version.
- Check your calendar. “Am I free Thursday afternoon?” or “What’s on my schedule next week?” (Calendar Integration must be connected — see below.)
- Take an action. “Archive this,” “label this as Invoices,” or “mark these as read.” Chiefy carries out the request in your inbox.
- Draft a reply. “Reply that we can confirm both rooms” — Chiefy prepares a draft in your voice for you to review. This is Smart Drafts working through chat.
I read the booking thread and drafted a warm reply confirming a 1pm early check-in is fine at no extra charge. It's saved to your drafts — want me to send it?
Search by meaning, not just keywords
When you describe what you’re looking for, Chiefy can search your inbox semantically — by the meaning of your request, not only the exact words. So “the email about the broken booking link” can surface the right thread even if it never used those words. If a keyword search fits better, Chiefy can do that too, and it chooses the right approach for what you asked.
Search-by-meaning is part of full access — it’s on during your free trial and on Pro. On the free plan, Chiefy still searches your inbox by keyword and filters.
Conversations remember context
Ask Chiefy is multi-turn. Within a chat session, Chiefy keeps the context of what you’ve already said, so follow-ups just work:
You: Find the latest email from the venue. Chiefy: (shows the thread) You: Draft a reply confirming Friday. Chiefy: (drafts a reply to that thread, no need to name it again)
Start a new chat any time you want a clean slate. Your past chats are kept, so you can reopen an earlier conversation from the history.
Using calendar features
Calendar questions — availability, what’s scheduled, event details — need Calendar Integration connected first. It’s a separate connection from your inbox. Until it’s connected, Chiefy can still help with everything in your email; it just can’t see your calendar.
If you ask a calendar question before connecting, Chiefy will let you know your calendar isn’t connected yet. See Connect and use your calendar to set it up.
Once connected, you can mix the two in one request — for example, “What did they propose, and do any of those times work for me?”
What you need
Ask Chiefy is part of every Chiefy account, but how much you can do depends on your plan. During your free trial and on Pro, you get full access. On the free plan, Ask Chiefy is more limited — you can still chat about your inbox, but with a weekly cap on messages, and search-by-meaning is a Pro feature. See Plans and your free trial for the details.
To use Ask Chiefy in Gmail, you’ll need the Chiefy extension installed and your inbox connected. The web app chat works once you’re signed in — no extension required. New to Chiefy? Start with Getting started first.
Was this helpful?
Thanks for the feedback.