The success of any collaboration platform depends, in part, on the ability of the system to enable employees with a problem to connect with employees who can solve that specific problem. But so far, collaboration platforms have struggled to deliver on expectations because they exist inside a collaboration paradox — employees typically need to invest their own time to gain the benefit of the tool, but they are reluctant to invest the time without an immediate benefit. Some firms are starting to use machine learning to break free from this collaboration paradox. This report highlights five vendors that are making strides in the right direction and provides CIOs with insights into various approaches to solving the collaboration paradox.