IBM's Watson Jeopardy system was a significant step forward in our ability to answer questions by connecting factual content in text to the questions it answers. This feat went well beyond the state of the art in information retrieval, and showed the promise of machines that can connect information together to solve users' needs. But the domains that complex organizations and businesses operate in are far more complex than Jeopardy, and present very challenging problems as we seek to give machines the power to offer genuine cognitive assistance. In this talk, I'll outline some of the ways in which IBM's Watson platform is already providing cognitive services that address complex, professional-level challenges, and I'll outline some of the many hard research problems we're seeking to address as we develop assistant cognitive computing systems with professional level competence.