Upgrading to Odoo 14 is crucial due to its speed enhancements, with it being three to four times faster than Odoo 13, along with improved features such as automated CRM and Outlook plugins. The migration process is essential for businesses as new versions are released annually, offering better functionalities and user experience. Odoo 14 focuses on simplifying tasks for users, enabling efficient communication, and enhancing sales activities through to-do lists and accurate customer data logging.