The purpose of this qualitative descriptive study was to explore how educators describe strategies used in contributing to the self-esteem of adolescent middle school girls. It was not known how educators describe strategies used in contributing to the self-esteem of adolescent middle school girls. The theoretical framework for this study was the Transformational Leadership Theory, which is an inspirational and motivational theory, promoting encouragement and trust. The research question for this study was "How do educators describe strategies used in contributing to the self-esteem of adolescent middle school girls." A purposeful sampling approach was used to recruit participants for this study. Data was collected through the use of an online questionnaire and one-on-one interviews. The sample size for this study was 25 participants for the online questionnaire and 10 participants for the one-on-one interviews. Four themes emerged from the analysis supported by the data sources: (a) Educators engage in building relationships through communication, the foundation of building, (b) Educators empower through affirmations, inspiration, empathy, and compassion, (c) Educators enhance self-esteem through programming, helping adolescent girls work through challenges, and (d) Educators encourage through leadership practices of being a role model, mentor, or supporter. The study findings revealed strategies that educators use with adolescent middle school girls in contributing to their self-esteem and align with the tenets of transformational leadership.