The external triggers cause transitions; to stay competitive, organizations create, respond to change, and shape the environment they interact with. The interactions manifest their traits as characteristics. Like biological species, organizations possess memes (or genotypes), memes mature as ideas or innovations, their interactions with the environment manifest as characteristics (phenotypes). IT organizations experience fast changes, for better response to change adopted agile software development (ASD). When phenotypes involve the development of affordances and display plasticity (agility), apart from cost-benefit criteria, it contributes to co-evolution among organizations and the environment. To examine the phenomena of co-evolution with diverse analytic and heuristic views, the author used multiple ASD case-studies from IT product/services organizations. The author noted that organizations increase the height of their fitness landscape, i.e., competitive advantage, by either developing and/or acquiring phenotypes. Acquisition meets cost-benefit criteria, but does not assist in sustaining the height, co-evolution, and/or cumulate as stable designs, thereby, there are inappropriate responses to external triggers.