The authors reveal the sign nature of the text which requires creating certain pedagogical conditions for better understanding. The article represents the hermeneutic perspective of studying process as the pedagogical process represents the text of culture created by its direct participants. The movement to pedagogical understanding through the sequence of text reading is shown: decoding of values, their interpretation, sense meaning, and the creation of the «counter» text by students. Attention is paid to the necessity of distinction between introductory, studying, searching and reflexive reading. The authors underline the dialogical nature of understanding, which allows the interpreters to find the hidden questions of the text, to look for answers to them, to analyze various positions, to allocate a concept, to create their own reflexive product. The understanding is shown in a circle: through the interpretation of subjects contents the people cognize themselves and the world around. Hence the interpretation of the text becomes personal-valued. Pedagogical conditions of understanding of the text in the learning process are the following: creation of situations of success; teachers’ commitment to implement the authors’ own position; use methods of self-expression: theater and game pedagogy; hermeneutical methods; understanding of the text through the decoding of signs, their interpretation and valuation of personal meaning. The hermeneutic orientation in the process of studying allows the teacher and the student to enter the world of culture.