Guided by a feminist communicology of organization framework, we examine generational growing pains by analyzing discourses appearing in HR Magazine at three different points in time, which approximately mark the midpoint of Baby Boomers’, Gen Xers’, and Millennials’ initial entry into the workplace. We reconstruct historically situated gendered discourses that encapsulate key concerns expressed by human resource management professionals as they dealt with younger generations of workers: Personnel Man as Father Knows Best (1970), Human Resource Specialist as Loyalty Builder (1990), and Talent Manager as Nurturer (2010). We propose that frustrations expressed by older generations about Millennials may not be because Millennials are necessarily more demanding than their predecessors, but instead because their expectations reflect and effect gendered changes of organizing.