Working under constrained conditions can boost or kill creativity, depending on the nature of the constraints (organizational, personal or task-related). However, a design process without clearly identified constraints, which set the project objectives, could lead to inefficiencies and unfruitful iterations. Some of the most acknowledged procedures to support requirement definition are focused on the use of specific checklists. However, notwithstanding the importance of the task, little attention was dedicated to the verification of the effectiveness of these tools. In such a context, the paper presents an investigation aimed at assessing the performance of three checklists that exploit different strategies to elicit requirements. To that purpose, a sample of fifty engineering students was asked to use the checklists to define the requirements for a specific design case. The outcomes of the experiment were assessed according to well-acknowledged effectiveness metrics, i.e. quantity, operationality, validity, non-redundancy, and completeness. The result of the assessment highlights that checklists based on more general questions or abstract stimuli can better support novice designers in making explicit internally felt design constraints that can potentially lead to more innovative design.