This thesis explores how digital communication can support compassionate leaders and compassionate workplaces. Through grounded theory methods, exploration and understanding emerged from compassionate leader semi-structured interviews. Emergent themes maintain digital communication can support the evolution of compassionate workplace connectedness and collaboration leading to a compassionate workplace experience. Compassionate leaders stimulating workplace compassion build an atmosphere of trust culminating in increased productivity and a joyful culture where one-on-one to multi-way interaction is supported by digital communication tools.