Understanding human interaction with a machine is a complicated task. Humans are creatures of nature and have spontaneous and irrational behaviors while machines are logical and process oriented. It is easy to see why interactions between humans and machines are a challenge for designers, developers, and engineers. Advances in technology have increased the capacity of machines to respond to humans in natural dialogue and everyday environments. This study hopes to contribute in understanding effective communication strategies between users and machines with the development of an instrument that incorporates best practices in user evaluation in human factors, cognitive response, and post evaluation surveys. This study will also evaluate participatory and cognitive computing metrics to understand their effectiveness and opportunities to increase efficient communication between a user and a machine.