This ~25-minute webinar from WestEd focuses on ways in which educators and education leaders can think critically about adapting technologies that help rather than distract students. The speaker contextualizes this topic by recognizing that many education technology tools have historically failed to achieve lasting impact in classrooms. As school districts question whether or not to invest in Generative AI, the speaker calls attention to patterns of uneven use of previous technologies and the abandonment of such tools despite initial enthusiasm. In this webinar, she offers a potential solution by suggesting that decisions be made with a “cultural-fit” lens. This lens encourages education leaders, educators, and education technology developers to reflect upon whether education technology or Generative AI tools reflect the culture and values of classrooms and schools. The webinar concludes with calls to action for all stakeholders to ask value-based questions and consider culture in decision-making processes regarding the adoption of new technology.