Chat with an Agent

Everything you need to know about chatting: selecting Agents, uploading files, using tools, voice mode, and more.

Cassidy’s Chat interface is where you interact with AI Agents, access your Knowledge Base, and run Workflows — all in one place.

To start a new chat, click New Chat in the sidebar or on Home. The Chats tab on Home is where you can find and reopen previous conversations.

You can also chat from your phone, through the Chrome extension, Outlook extension, Microsoft Office extension (Word, Excel, and PowerPoint), and external deployments like Slack, Microsoft Teams, Google Chat, email, embed, and API.

Find chats and resources

Click Search in the sidebar, or press Command + K on a Mac or Ctrl + K on Windows. You can search your chats, meetings, Agents, Workflows, projects, Skills, files, and Cassidy help articles from one place. Use the tabs at the top when you want to narrow the results.

Search only shows resources you can access. Draft Agents, Workflows, and Skills do not appear because they are not ready to use.

Choosing a result takes you to the most useful next step. Agents start a chat, Workflows open in the Run view, Skills are added to a new chat, projects filter the Chats tab, and files open in a preview. You can also search for destinations such as Account Settings → Notifications.

Select an Agent

Every chat uses an Agent. You can switch between custom Agents, foundational models, and Cassidy’s pre-built Agents at any time.

1. Open the Agent dropdown

   Click the Agent dropdown at the top of the chat or in the text box to see your options.

   
2. Browse and choose an Agent

   You’ll see three categories:

   • Custom Agents — built by your team, trained on your Knowledge Base with tailored instructions
   • Default Agents — foundational models like GPT, Claude, Gemini, and Open Source models without your business context
   • Pre-built Agents — Cassidy’s ready-made options like the Data Analyst and Cassidy Help Agent

   Default Agents don’t have access to your company’s Knowledge Base or custom instructions.

   
3. Pin an Agent

   Hover over a published Agent, open its … menu, and select Pin to sidebar. Pinned Agents appear in the Pinned section of your sidebar and near the top of the Agent list. Draft Agents must be published before you can pin them.

   
4. Switch mid-conversation

   Need a different Agent? Click the dropdown again and select a new one. The chat continues with the new Agent — no need to start over.

When chatting with a Q&A Agent, responses include source citations that link back to your Knowledge Base so you can verify the information.

Personalize your chat

Tell Cassidy your name, role, and response preferences so every chat is tailored to you, no matter which Agent you use. Open Customize → Personalization from the sidebar or from the top-right corner of a new chat.

See Personalize your chats for the full walkthrough and where your preferences apply.

For organization-wide AI behavior rules that apply to every Agent and Workflow, see Global instructions.

Agents can also remember useful context from your private chats and search your past chats when you refer back to earlier work. See Memory to learn how it works and how to manage it from Customize → Memory.

Reference your Knowledge Base

You can pull specific items from your Knowledge Base directly into a chat to ask targeted questions.

1. Type the # key

   In the chat text box, type # to open a search dropdown for your Knowledge Base.

   
2. Search and select an item

   Start typing keywords to filter results. Click the item you want to reference — it appears as a tag in your message.

   
3. Ask your question

   Send your message with the referenced item. The Agent uses that specific document as context for its response. For example:

   • “Can you summarize the main points of this employee handbook?”
   • “How many vacation days am I entitled to according to this policy?”
   • “What is the process for requesting time off?”

The # reference is useful when you want to point the Agent at a specific document for a single question. To have an Agent always search certain Knowledge Base items, add them to the Agent’s configuration — see Build and configure an Agent for details.

The # picker can include recorded meetings, not only Knowledge Base items. To search across your meeting library in chat (with citations back to recordings), add the Meetings Connector to the Agent — see Chat with your meetings.

Upload files and media

Share files, images, videos, and audio directly in chat to ask questions about their content. These uploads are temporary — they are not saved to your Knowledge Base.

1. Click the + button

   In the bottom-left corner of the text box, click + to open attachment options.

   
2. Choose your upload type

   Select Attach a File or Attach an Image from the menu. You can also drag and drop files directly into the chat window.

3. Ask questions about the content

   Once uploaded, the Agent can analyze the content. Try prompts like:

   • “Summarize the key findings in this report”
   • “What text is visible in this screenshot?”
   • “Extract the data from this chart”

   

Uploaded files are temporary and tied to the chat session. If you need to store a file permanently, upload it to your Knowledge Base first, then reference it with #.

Use the tools picker

Click Tools at the bottom of the text box to see everything available in the current chat. From here you can turn capabilities such as Web Search, Image Generation, Artifacts, and Browser Use on or off for the chat.

The menu also lists your Connectors. Your own Connectors follow your account settings rather than per-chat toggles. Select Add connector to browse apps or Manage connectors to reconnect, change action permissions, or turn a Connector off. Connectors the Agent’s builder added appear under Enabled on Agent. A warning icon means you need to reconnect.

Code Execution & File Creation is configured on the Agent itself. New custom Agents have it enabled by default. If it is missing, edit the Agent and enable Code Execution & File Creation under Customize > Advanced Settings.

Use voice mode

Voice mode lets you have a spoken conversation with your Agent instead of typing. Click the microphone icon in the text box to start speaking. The Agent transcribes your speech, processes it, and responds — both in text and, optionally, with audio playback.

Use the writing editor

The writing editor is a side-by-side panel where you can draft and refine content while chatting with an Agent.

1. Open the editor

   Click Open editor in the top-right corner of the chat interface.

   
2. Write alongside your chat

   Type directly in the rich text editor while chatting with the Agent. This is useful for researching ideas, drafting content, or getting real-time writing assistance.

   
3. Add Agent responses to the editor

   When the Agent generates something you want to keep, click Add to Editor on the message. The content is automatically added to your document.

   
4. Save to your Knowledge Base

   Click File then Save to Knowledge Base to store your document permanently. Choose a name and folder location, then click Save.

   

   

   You can also export to Microsoft Word or PDF format.

   Once saved, changes sync automatically between the writing editor and the Knowledge Base document.

The writing editor is tied to each individual chat. Save your work to the Knowledge Base before closing if you want to keep it.

Run a Workflow in chat

You can execute Workflows directly within a chat conversation to automate tasks without leaving the interface.

1. Open the Workflow menu

   In the text box, click the Workflows button to see available Workflows.

   
2. Select a Workflow

   Choose the Workflow you want to run from the list.

3. Fill out the form

   A form replaces the text box with input fields for the Workflow. Fill in the required information.

   
4. Generate and review results

   Click Generate to run the Workflow. Results appear directly in the chat.

   
5. Continue the conversation

   After the Workflow runs, you can ask follow-up questions, refine inputs, or explore the results further in the same chat.

Use a Skill

Skills give Agents reusable procedures, files, and tools for specialized tasks. Installed Skills are available across your chats, while Agent-attached Skills are available whenever you use that Agent.

Agents choose relevant Skills automatically based on each Skill’s name and description. To select one yourself:

1. Open the slash menu

   Type / in the chat box.

2. Select a Skill

   Choose a published Skill under Current Agent’s Skills or My Skills.

   
3. Describe the task

   Continue writing your request and send the message. The Agent reads the selected Skill before responding.

See Use Skills in chat and Workflows to install Skills and understand automatic selection.

Use the prompt library

The prompt library lets you create reusable prompt templates so you can quickly apply consistent instructions across chats.

Manage your prompts

1. Open the prompt library

   In the chat text box, type / and click Manage prompt library from the menu.

   
2. Create a new prompt

   Click + New prompt. Describe what you want, and Cassidy generates a refined prompt for you. Or click Create prompt manually (advanced) to write it yourself.

   

   

   When writing prompts manually, you can:

   • Use [brackets] for placeholders that change each time (e.g., [professional] or [witty] for tone)
   • Type # to reference Knowledge Base items
   • Add example outputs so the Agent matches your preferred style

   
3. Save and use

   Click Save to store it. You can then click Use prompt to apply it immediately.

   

Prompts created in the library are visible to everyone in your organization.

Apply a prompt in chat

1. Type / to open the prompt menu

   The menu shows Cassidy’s default prompts (like Improve writing and Summarize) and your custom prompts.

   
2. Insert and customize

   Click a custom prompt to insert it. Replace any placeholders with your actual values — these edits do not change the saved template.

   
3. Send and get results

   Send the message. The Agent generates a response using your prompt template.

   

For default prompts like Improve writing or Summarize, a quick form appears where you paste your text and click Generate.

Analyze data

Upload spreadsheets or data files and let the Agent create charts, run calculations, and extract insights.

1. Select a data-capable Agent

   Choose the Data Analyst default Agent, or use a custom Agent. New custom Agents have Code Execution & File Creation enabled by default.

   
2. Upload your data

   Click + and attach a CSV or Excel file, or drag and drop it into the chat.

   
3. Ask questions and request visualizations

   Describe what you need:

   • “Create a bar chart showing sales by region”
   • “What are the key trends in customer behavior?”
   • “What was the total revenue for Q1?”

   
4. View the code behind the analysis

   Click Analyzed sources in the results, then click the code icon (</>) next to any step to see the Python code the Agent used to process your data.

   

   

How to format your data for best results

• Use CSV or Excel format — these are the only supported file types for data analysis
• Organize data in rows and columns — each row is a record, each column is a variable
• Include descriptive column headers in the first row — avoid blank rows above the headers
• Keep data consistent — no empty rows between entries, no multiple tables in one file, avoid multiple worksheets

Beyond traditional data analysis

Code Execution & File Creation can also:

• Manipulate branded templates — fill out forms, convert reports to presentations, edit Word documents and PDFs
• Create synthetic data — generate sample datasets for testing or demonstrations

For more on generating files, see Create files in Cassidy.

Edit and regenerate messages

You can modify a sent message and have the Agent generate a new response.

1. Hover over your message

   Move your cursor over the message you want to change. An edit icon appears on the right.

   
2. Edit and re-send

   Click the edit icon, modify your text, and press Enter. The Agent generates a new response based on your updated message.

   
3. Browse response versions

   Click the left and right arrows at the top of the Agent’s response to cycle through all generated versions.

   

You cannot edit Agent messages directly, but you can click Regenerate to produce a new response with the same prompt.

Branch a conversation

Branching creates a copy of a conversation up to a specific message, so you can explore a different direction without losing the original thread.

1. Find the branching point

   Open a chat and scroll to the message you want to branch from.

2. Branch in a new chat

   Click the … menu below the message and select Branch in new chat.

   
3. Continue in the new chat

   A new chat opens in a separate tab with the full conversation history up to that message. The original chat remains unchanged. The new chat is labeled “Branched from [Chat Title].”

   

   

Share and organize chats

Chats use the same sharing model as Agents and Workflows — you can share with specific teammates, groups, or your whole organization, and set each person’s access to View (read-only) or Edit (can send messages).

Share a chat

Open the … menu on any chat and select Share, or click the Share button in the chat header. Choose who can access it and set their permission level. Sharing a chat does not notify the recipient — you’ll need to send them the link directly.

Organize chats with projects

Projects keep related chats together, like everything for a customer account, hiring process, or quarterly planning. Chats in a project share the project’s instructions, memory, and access. Open a chat’s … menu and select Move to project to add it to one.

See Projects to create, customize, share, and delete projects.

Chats that teammates share with you appear in Recents once you open them. To see them right away, open the … menu beside Recents, choose Chats shared with me, then select Always show.

Keep these things in mind when sharing chats:

• Chats inside a project use the project’s sharing settings and cannot be shared individually
• New messages added to a shared chat are visible to everyone with access in real time

Use Cassidy in multiple languages

While the Cassidy interface is in English, the AI models can understand and respond in virtually any language. Type your message in the language you prefer, and the Agent responds in the same language.

If the Agent doesn’t consistently use your preferred language, add a specific instruction to the Agent’s settings — for example, “Always respond in Spanish.”

For more on customizing Agent behavior, see Build and configure an Agent.

Next steps

Build and configure an Agent

Create a custom Agent with tailored instructions and Knowledge Base access.

Choose the right AI model

Compare GPT, Claude, Gemini, and Open Source models to pick the best model for each task.

Prompt engineering guide

Write effective prompts for better, more consistent AI outputs.

Create files in Cassidy

Generate documents, spreadsheets, and presentations through chat.