Many of the best companies to work for in the US have found that they are benefiting from implementing flexibility and family friendly policies for their employees, but they also found some challenges with their implementation. Of course, generational attitudes, COVID-19, globalization, and other types of environmental and economic dynamics have propelled organizations to increase these types of offerings and policies within all types of workplace settings. And, in many cases their enactment has been more complex than expected. And, for implementation of such policies, it is important to understand the possible available options and their benefits and challenges. This article will highlight the challenges.