Digital transformation impacts an ever-increasing amount of everyone’s business and private life. It is imperative to incorporate user requirements in the development process to design successful information systems (IS). Hence, requirements elicitation (RE) is increasingly performed by users that are novices at contributing requirements to IS development projects. [Objective] We need to develop RE systems that are capable of assisting a wide audience of users in communicating their needs and requirements. Prominent methods, such as elicitation interviews, are challenging to apply in such a context, as time and location constraints limit potential audiences. [Research Method] We present the prototypical self-elicitation system “LadderBot”. A conversational agent (CA) enables end-users to articulate needs and requirements on the grounds of the laddering method. The CA mimics a human (expert) interviewer’s capability to rephrase questions and provide assistance in the process. An experimental study is proposed to evaluate LadderBot against an established questionnaire-based laddering approach. [Contribution] This work-in-progress introduces the chatbot LadderBot as a tool to guide novice users during requirements self-elicitation using the laddering technique. Furthermore, we present the design of an experimental study and outline the next steps and a vision for the future.