Discourse analysis is a promising qualitative research approach across social science disciplines for analyzing the construction of reality in a variety of organizational and institutional arenas. However, conducting empirical discourse analyses remains challenging. In this paper we identify four key challenges involved in doing discourse analysis and then recommend several “tools” derived from empirical practice to address these challenges. We demonstrate these recommendations by drawing on examples from a discourse analysis study we conducted, of strategic management discourse in public education. Our tools and recommendations aim to facilitate conducting and writing up discourse analyses and may also contribute to addressing the identified challenges in other qualitative methodologies.