Infrastructure and operations (I&O) professionals who manage unified communications (UC) must decide how to incorporate public connections based on Skype software. HEROes in today's enterprises routinely take technology into their own hands to solve customer problems. Thus, these empowered employees won't tolerate the barriers to collaborating with external parties that internally deployed UC systems often impose. So what should I&O professionals do? In this report, we lay out four potential approaches to Skype in the enterprise.