One of the main aims of diverse education systems is the development of key competences to improve citizens’ capacity for lifelong learning. However, some authors have signalled the challenge their measurement entails, among them the Learning to Learn (LtL) competence, which has also been shown to be complex to define and is under research. With a pre–post-test design and a variety of assessment instruments, this study compares the effect having an educational technology course and using telecollaboration has on the development of the LtL competence in a content and language integrated (CLIL) learning environment. Four groups of teacher trainees at two different universities took initial and after treatment surveys on LtL. Quantitative and qualitative data analysis indicated that technology boosts LtL but that telecollaboration helps develop LtL reflective concepts further in the form of processes by constructing or accomplishing learning goals in similar contexts.