Your first chat
Chatting with Toby works like messaging a capable assistant. Ask in your own words. There are no special commands to learn.
Start a chat
Click Chats in the sidebar, or press ⌘N from anywhere in Toby. Type in the box and press Return to send (Shift+Return adds a new line).

Not sure what to ask? Click a suggestion under the message box to fill it in, then edit it or press Return.
Five things to try
Copy any of these into a new chat. Each one uses an app you connected in the previous step.
- "What's on my calendar today, and do I have any conflicts?"
- "Summarize my unread email. What needs a reply today?"
- "What tasks are due this week? Which one should I do first?"
- "Remind me to call the dentist tomorrow at 10am."
- "Draft a reply to the latest email from Sam saying Thursday works."
Toby shows a collapsed Working… section while it checks your apps. Click it to see each step it took. When it's done, the answer appears below your message.

:::tip Ask for a draft first Toby acts on what you ask. It sends an email if you say "send", so be specific. If you'd like to review something first, ask for a draft. When a request is unclear, Toby asks a quick question and gives you buttons to choose from. :::
Have a conversation
You can follow up without repeating yourself:
You: What meetings do I have tomorrow?
Toby: You have three: Design review at 10:00, 1:1 with Priya at 13:00, and Vendor call at 15:30.
You: Move the vendor call to Friday at the same time and let them know.
Share files and pictures
Click + in the message box to attach a PDF, image, or document, then ask about it: "Summarize this contract and list the key dates." You can also paste a web link and ask Toby to read it.
When Toby creates a file for you, such as a report or a list, the reply includes Download and Open buttons.
Pick a different persona
A persona changes Toby's style and focus. For example, Mailman is tuned for sorting email. To use one, click the arrow next to + in the chat toolbar and choose Chat with Mailman. To change which persona new chats use, click the persona name at the bottom of the sidebar.
Ask Toby about Toby
Toby can answer questions about its own setup: "Which apps are connected?", "How do I set up Jira?", or "What can you do with my calendar?"
Next steps
- Things to try: more ideas, organized by situation
- Toby app tour: find your way around the app
- Memories: teach Toby your preferences