This paper seeks to contribute insights from an inquiry into how some students at Singapore Polytechnic (SP) viewed Self-Regulated Learning (SRL) strategies in a blended professional communication skills module in relation to their ability to manage their learning and self-development. SRL strategies may serve as drivers of students’ ability to participate and develop in self-directed learning, and our findings indicated that respondents had positive beliefs about their value. However, these beliefs were rooted within conditions relating to the perceived practical value of the strategies for the given context and application, fit with personality, and ease-of-use, which informed or influenced students’ choices of learning strategy. Although this paper did not originate within a CDIO context, and is not specific to engineering students per se, engineering students were among the multi-disciplinary mix of respondents in the study, and we find that our insights may hold relevance for CDIO Standard 2 learning outcomes, as presented in CDIO Syllabus v2.0 (Crawley, Malmqvist, Lucas & Brodeur, 2011) in terms of topic 2.4 (Attitudes, Thought and Learning), specifically 2.4.2 (Perseverance, Urgency and Will to Deliver, Resourcefulness and Flexibility), 2.4.5 (Self-awareness, Metacognition and Knowledge Integration), 2.4.6 (Lifelong Learning and Educating), and 2.4.7 (Time and Resource Management). The insights may inspire us to give attention to how our students think and operate, help us reflect on the roles we play as educators, and offer some ideas as to the learning designs we might consider as well as other on-the-ground work that we need to do to support our students’ cultivation of self-regulatedness, self-directedness and life-long learning.