Purpose: The purpose of this paper is to illustrate how associationism mistakenly assumes that direct experience is possible; that is, there is expectation-free observation and association without prior expectation. Thus, associationism assumes that learning involves the absorption of information from the environment itself. However, contrary arguments take the position that, for an individual to make a connection between his/her behaviour and its consequence(s), he/she must first have an expectation in order for a connection to be made. Design/Methodology/ Approach: This paper uses a personal experience to illustrate how implicit assumptions and unstated expectations can be found in the corporate world. It offers to answer questions that will lead to an examination of overcoming irrationality through utilization of the Popperian philosophy of associationism. Findings: When evaluating a practice, it is easier to find evidence of some sort to support the practice, especially if we are either disposed to do so or if our colleagues and organizations have recommended that we adopt these practices. However, if we are committed to genuinely improving our practice, Swann (2009) suggests that we become critical and ask, "What are the unintended and undesirable consequences of doing things this way?" (p. 8). Research Limitations/Implications: Popper's approach needs to be developed or learned through stages and with time. We need to be aware that it takes time to master the use of this approach. Merely introducing or having organizations learn the different methods or short cuts have only a limited effect in improving their ability to deal with issues in different contexts. Practical Implications: The examples used throughout this paper illustrate that the adoption of Popper's approach does not necessarily require large-scale experiments. In fact, a well-conducted case study can be effective in casting doubt on existing assumptions. Regardless of the nature of the research strategy and the scale of the experiment devised to test a hypothesis, the task of testing can and will be problematic. Social Implications: Expectations can make us look foolish from time to time, but they can also be very powerful or useful because they are more than mere anticipation. If we are unable to strip away our preconceptions or prior knowledge, we can at least acknowledge our biases and, in doing so, we may not continue to be trapped within our own perspectives, which can blind us to the truth. Originality/Value: The examples used in this paper illustrate that Popper's approach is robust and applicable in a variety of contexts and is not limited to educational organizations. Furthermore, it showcases our irrationality, and helps us understand when and where we may make erroneous decisions.