This paper reports on a teaching strategy which aims to help Japanese English as a Foreign Language (EFL) high school students develop their essays to meet readers’ expectations. The author encouraged his students to write their essays sentence-by-sentence by answering three questions, “Why so?,” “Such as?,” and “And then?,” which are provided as springboards to achieve coherence and reader relevance. This strategy is intended to make the transition from one sentence to another accountable to readers, thus enhancing the communicability of the entire passage. In 2023, the author practiced this strategy in class and in an extracurricular on-demand course to confirm its effectiveness and develop teaching materials based on it.