In a method of fitting of a hearing device having an input transducer and an output transducer, the method includes executing a fitting application on a graphical user interface of an external device in communication with the hearing device, detecting by measuring reactions of the user to picked-up sound, performing acoustic feedback measurements as a background process without a user's involvement, assessing the probability of a correct physical fit based on the position of the inserted hearing device, assessing feedback risk based on the correct physical fit assessment and the acoustic feedback measurements, and fine tuning fitting parameter of the hearing device based on the result of at least one of the detected reactions of the user, acoustic feedback measurements and saved, within the fitting application, personal information of the user.