PURPOSE : The plight of dissatisfied employees has become a recurring theme. A question often asked by management trainees is “How do I handle my difficult boss?” Hence, this paper aims to address the difficult boss problem successfully from the perspective of the subordinate. DESIGN/METHODOLOGY/APPROACH : The conceptualized legacy framework had been presented to participants and who verified its accuracy by their experiences. They could apply the framework with relative ease. Workshops, interview and online questionnaires informed the development of the framework. FINDINGS : The framework proposes four legacy effects on subordinates that bosses leave after interaction, namely, tense, dark, false and calm legacies. The legacies assist subordinates in classifying their bosses as either a hammer, flat battery, fire-lighter or dynamo. Once the boss is categorized, strategies to assist subordinates in handling their difficult boss flow from the framework. RESEARCH LIMITATIONS/IMPLICATIONS : While extremely useful for subordinates, bosses are limited in the use of the legacy model as it requires very high trust levels to exist. The nature of the difficult boss problem suggests that such trust does not exist. PRACTICAL IMPLICATIONS : Benefits of understanding the legacy framework has two benefits: subordinates can use the legacy tool to classify their bosses and find strategies for how to handle difficult bosses. For bosses, subordinate evaluation of their legacies presents an alternative avenue to seek feedback and improve “self-learning” through reflection. ORIGINALITY/VALUE : The legacy matrix was shown to be applicable to all bosses at all levels in virtually all organizations. The value of the framework was also observed at the informal level.