As organizations collect an increasing volume of data, their employees and vendors are tasked with making sense of it. This is done for a multitude of reasons – to create future strategy, develop products, understand customers, and a myriad of others. But data for data’s sake can lead to confusion. Without a clear vision or idea, being given troves of data without instruction can lead to bad analytics, flawed insight, and ineffective strategy. In this paper, we will provide examples, based on our experience with the US Air Force (USAF) Air Education Training Command (AETC) Pilot Training Next (PTN) initiative, of what happens when too much data is presented, and common pitfalls that arise when analysts are not given a clear mission or guidance. We will discuss PTN’s data driven system architecture and analytic strategy as it evolved, while providing a state of the art learning platform to new student pilots. Lastly, we will provide recommendations for organizations to prevent these mistakes, as well as provide best practices and behaviors to nurture better data literacy, strategy, and mission creation which will help accelerate training system adaptation and innovation to an unexpected future. This paper is intended for program managers and leaders, and no data analytics background is assumed.