In this paper we investigate how to efficiently empower teachers to implement and orchestrate a mathematical learning activity supported by digital technologies. The particular learning activity in this study is intended to facilitate learners’ transition from the Pythagorean Theorem to the distance formula and the equation of a circle. The activity comprises structured and guided inquiries involving laptops with GeoGebra and traditional resources. It has been tested with 38 upper secondary students and two mathematics teachers. Our results indicate that a singular discussion with the teachers, based on the researcher’s prospective analysis of the activity with main focus on threshold constructs and self-regulating skills, suffices to support the teachers’ implementation and orchestration of the activity.