While measuring the performance of collaborative research and development (R&D) projects is critical for both practitioners and academics, it is rarely straightforward in practice. Based on first-hand experience of the performance measurement practice within an extensive, long-term, Swedish innovation programme named Smart Built Environment, this chapter provides a reflective account of the setup and challenges experienced. The programme was launched in 2016 and is a long-term initiative of up to 12 years. Backed by three state research agencies, it is, to date, the single largest investment in innovation, R&D in digitalisation made in the Swedish built environment sector. This chapter is written as a collaborative autoethnography, with three out of the five authors having had first-hand experience of the specific measurement initiative analysed. The chapter describes how the visionary objectives of the programme, related to sustainability, time, cost, and business logics, were developed and operationalised in practice. Furthermore, it is explained how several emergent challenges related to ambiguity in goal formulation, adaptation to contingencies of moving targets and temporal scope, and development of a multiplicity of assessment methods, were managed.