This research uses heuristic inquiry to provide insight into experiences of generating questions in coaching. Eight experienced coaches, recruited as co-researchers, shared their experiences of generating coaching questions via post-coaching reflections and conversational interviews. Thematic analysis of the data identified that coaches noticed a wide range of elements when forming questions. Questions frequently ‘pop’ into the heads of coaches, accompanied by somatic sensations. When asking questions, coaches used prefacing statements for their own or their client’s benefit. Inner dialogue was experienced, often in the form of meta-questioning. This research highlighted three paradoxes that coaches tried to balance while enquiring of their clients. Suggestions for future research are also proposed.