Through the Chat tab:
Click on the Chat tab in the left navigation bar.
Click on Browse chat then select Direct Messages
You can search for the person's name by typing in the search bar or by scrolling through the list of names
Click on the name to start sending direct messages.
Once you have started a conversation, the person's name will appear under the Recent messages.
Through the Message tab:
Click on Message tab at the bottom left corner of the screen.
Search for the name of the person you would like to chat to and click on it.
A chat box will open at the left side corner where you can start sending direct messages.
Through Task Properties
Click on a Task
Click on the Assignee/Member you want to chat with
Select Send a Direct Message