Developing new technology for artistic practice requires other methods than classical problem solving. Some of the challenges involved in the development of new musical instruments have affinities to the realm of wicked problems. Wicked problems are hard to define and have many different solutions that are good or bad (not true or false). The body of possible solutions to a wicked problem can be called a design space and exploring that space must be the objective of a design process. In this paper we present effective methods of iterative design and participatory design that we have used in a project developed in collaboration between the Royal Institute of Technology (KTH) and the University College of Opera, both in Stockholm. The methods are outlined, and examples are given of how they have been applied in specific situations. The focus lies on prototyping and evaluation with user participation. By creating and acting out scenarios with the user, and thus asking the questions through a prototype and receiving the answers through practice and exploration, we removed the bottleneck represented by language and allowed communication beyond verbalizing. Doing this, even so-called tacit knowledge could be activated and brought into the development process.