In the context of the global trend of designing sustainable structures, the attention towards high-rise timber buildings of 8 to 25 storeys has been increasing in recent years. Balloon construction technique using a relatively new heavy timber material, cross-laminated timber (CLT), has been shown to be promising for high-rise building applications, given its compatibility with off-site construction techniques and its desirable mechanical characteristics. To date, tall timber buildings using CLT have been built mainly in non-seismic or low-seismic locations around the world, whereas their application in high seismic regions has been limited to platform construction. More research on the behaviour of CLT structures during seismic events in terms of system behaviour as well as the behaviour of components, particularly connections, is required. The research presented in this paper seeks to initiate the process of seismic design of tall wood buildings using a balloon construction technique. Two buildings, one three-storey fictitious building and one to-be-constructed ten-storey building, both located on the west coast of Canada, were considered and designed based on the NBCC 2015 seismic provisions. The loads on the shear walls, which span over three storeys, were extracted in order to estimate realistic demands on lateral load resisting systems (LLRS) in the balloon construction. Different connections, including base shear connections, panel-to-panel shear connections, as well as high-capacity hold-downs, were designed accordingly. An experimental program was developed to investigate the behaviour of these connections, focusing on yielding and failure mechanisms in each connection category. This paper explains different phases of the experimental program and introduces connection details designed to achieve the research goals. The results of this study will contribute to the body of knowledge on seismic behaviour of prefabricated mass timber buildings, and will benefit engineers and practitioners using timber to design high-rise structures.