The present technology provide a mechanism for displaying and initiating actions and workflows for objects with a single drag-and-drop operation in association with a content management system. Drag operations may be monitored to trigger monitoring of a pointer performing the drag operation to detect whether the pointer is within a threshold distance from a chosen aspect, such as a system tray icon, and/or an area of a temporary invisible window. Upon detection, the drag operation of the objects may seamlessly trigger a presentation of a menu window. The menu window may display one or more icons representing different actions and workflows for which the object may be dropped, via a drop operation, upon to indicate a selection.