Masking and compensation frequently obscure ADHD in girls and women, delaying recognition and shaping profoundly different developmental trajectories. This interactive workshop presents a structured mother–daughter dialogue model to illuminate how ADHD presents, evolves, and is recognized across generations. Through a live, guided conversation contrasting early diagnosis in adolescence with late diagnosis in adulthood, participants will examine how high achievement, relational sensitivity, emotional overregulation, and self-imposed compensation can conceal executive dysfunction. At key inflection points, the dialogue pauses for clinical analysis, highlighting what facilitated early identification in one pathway and what prolonged concealment in the other. Participants will explore how gendered expectations, internalized standards, and assessment language influence disclosure and diagnostic timing. Small-group reflection will invite attendees to identify masking narratives in their own clinical or personal contexts. The workshop integrates lived experience with applied clinical insight, offering practical tools including dialogue-based inquiry techniques, validation strategies, and structured prompts that help differentiate competence from overcompensation. By examining how timing of diagnosis shapes identity formation, emotional outcomes, and coping strategies, participants will leave with concrete strategies to support earlier recognition of ADHD in girls and women and to refine assessment practices across the lifespan.