This paper aims to tackle challenges of managing projects in highly virtual and fluid contexts, characterized by diversity, dispersion, digital dependence, unstable membership, and dynamic coordination and configuration. We investigate project leaders’ personality and emotion expressed in written expression and examine their impacts on collaboration outcomes. IBM Watson Personality Insights and Tone Analyzer were adopted to assess the leader’s personality and emotion. A computation model to classify collaboration patterns into taskwork-related and teamwork-related communication is under development. We report preliminary findings based on 417 weekly meetings between October 2018 and February 2020 in 8 open-source software teams around WordPress. The research results have the potential to inform researchers and practitioners about what personality profiles and emotions should be considered to foster collaboration in virtual and fluid projects. It is possible to extend the boundary condition of the traits school of leadership for project management in the new context.