Attainment of the “trusted advisor” role for sales representatives in a complex sales environment is considered the pinnacle of buyer-seller relationships. This study also examines whether pervasive smartphone use particularly among the millennial generation has substantially altered behaviors in the form of communications in the buyer-seller relationship. Does replacement of face-to-face and direct verbal communications by impersonal technology based communications that removes verbal and non-verbal or behavioral forms of communications have an impact on perceptions of communication quality and trust building among the parties. As use of smartphones for text based communications is more prevalent among younger generations, can generational differences provide insight into any change in the underlying information exchanges and supportive behaviors expected in development of a “trusted advisor” relationship. In order to examine this question, the study sought to measure antecedents of the “trusted advisor” construct including communications quality (Neu, Gonzales & Pass, 2011), trust in an organizational setting (Mayer, Davis & Schoorman, 1995) and a nominal scale of trusted advisor roles based on the work of Maister, Green and Galford (2000). Survey results confirm the antecedents as components and propose a regression model for measurement of the presence of the “trusted advisor” construct.