The method provides for receiving a draft message that includes recipients of the draft message, content of the draft message, and zero of more attachments included with the message, from a sending user. A pre-determined number of properties are determined from the draft message, which include information about the sending user, the recipients of the draft message, a subject and content of the draft message, and a sentiment of the draft message. The draft message properties are submitted to a pre-trained classifier model trained by supervised machine learning techniques to recommend whether a meeting held with the recipients or a delivered communication to the recipients is recommended for the draft message, and responsive to receiving a recommendation of a draft meeting with the recipients from the classifier model, presenting the recommendation of a meeting with the recipients to the sending user.