Nice read, Sam.
Quick question — Is the assumption that people would be using voice to invoke Cortana in the workplace? My understanding is that Cortana works with all the forms of input and all the form factors, and that is precisely why it would work in the workplace — because people can interact it with mouse, keyboard, touch etc., in addition to voice.
So on a Desktop form factor, Cortana is no different than any other bot that can be interacted with using a keyboard., As long as it gives contextually relevant information in a given work environment for a given form factor, voice invocation doesn’t really matter. Perhaps a broader discussion should be around the relevance of virtual assistants in the modern information workplace and how they could evolve to facilitate the existing work flows.
As an extension, among the 4 dominant voice interfaces (Alexa, Siri, Google Now and Cortana), Cortana is probably still more of an “it” than a “her”. This is partly because Microsoft hasn’t offered a compelling voice experience with Cortana yet, and people are probably not conditioned to associate tradition mouse and keyboard interactions in a box with a gender.
Therefore, if the end goal is to have voice interfaces in the workplace, that would inevitably require new form factors and new experiences that completely transform the way we use information tools at work. Next 10 years are going to be very exciting!