This paper aims to show the koan as a literary genre in Milan Dekleva's collection of poems Preseženi človek (The Transcendent Man). The koan, a Zen Buddhist saying, is a terse, paradoxical text. Its main goal was a test of enlightenment, which had to be attained by every Zen disciple. The test was conducted through a dialogue between a master and a disciple in the linguistically compact form of the paradox. Dekleva's koans show that he belongs to Zen thinking, since it is through a paradox that the poet tries to clarify essential questions of existence which are unknown to Western metaphysics: question of emptiness, silence, enlightenment and the identity of all that exists. Dekleva's koans involve problems of Slovene contemporary literature: the end of the subject and metaphysical dualism, the problem of language in terms of original emotion and the question of a new ethics of compassion for all sentient beings. This paper also considers the French modernist René Char, to whose poetry of sayings Dekleva has devoted attention.