The article discusses the practice of dialectical questions in coaching and the associated basic methodological approaches that can be applied during coaching psychology work. The investigation concentrates on a description of three basic elements: 1) how to collect knowledge through questions 2) the importance of viewing knowledge from different angles in collaboration with the coachee, 3) to encourage the coachee to create a plan for future actions. Through a case study, a number of considerations related to dialectical questions are illustrated