Building software, like building almost anything, requires people to understand a common goal and work together towards it. In large software companies, a VP or Director will have an idea or goal and it is often the job of middle management to distill that lofty, general idea into manageable, finite units of work. How do organizations do this hard work of setting and measuring progress towards goals? To understand this question, we undertook a mixed methods approach to studying goal setting, management dissemination of goals, goal tracking and ultimately software delivery at a large multi-national software company. Semi-structured interviews with 47 participants were analyzed and used to develop a survey which was deployed to a multi-national team of over 4,000 engineers. The 512 responses were analyzed using thematic analysis, linear regressions and hypothesis testing, and found that tracking, measuring and setting goals is hard work, regardless of tools used. Middle management seems to be a critical component of the translation of lofty goals to actionable work items. In addition, attitudes and beliefs of engineers are critical to the success of any goal setting framework. Based on this research, we make recommendations on how to improve the goal setting and OKR process in software organizations: invest in the data pipeline, increase transparency, improve communication, promote learning communities, and a structured roll out of OKRs.