Education and training is widely acknowledged as being one of the key factors for leveraging organisational success. However, it is equally acknowledged that skills development and the acquisition of learning through managed cognitive approaches has yet to provide a "perfect" match. Whilst it is argued that an ideal learning scenario would be one that is distinctly tailored to meet individual learner preferences (learning styles), and customisable to meet pedagogic needs; in reality, there are a few more steps needed. For example, the specific context of education and training per se, through "traditional" education and training delivery approaches are now going through a paradigm shift in order to provide learners with a better overall learning experience. Personalised Learning Environments (PLEs) are now being used to address learners' needs and preferences through mature technological solutions such as managed Virtual Learning Environments (VLEs). Evidence highlights that learners can learn better with a bespoke (tailored) PLE's, as the deployment of teaching and learning material is augmented towards their individual needs. Moreover, from an organisational perspective, efficiency gains have also been acknowledged using this approach, as learners using managed learning environments are generally more engaged with the learning process. In this respect, there is an exigent need for organisations to evaluate how managed learning can be more effectively aligned to organisational strategy, so that business goals can be more purposefully executed. This requires decision-makers to not only understand the core business functions, processes and critical success factors (organisational need); but also the training, learning and development needs of staff within the organisation (intellectual capital). For example, it is important to appreciate how organisational strategy "drives" education and training through organisational systems and procedures in order to procure organisational success. This paper reports the findings from the development of a conceptual Diagnostic Learning Styles Questionnaire (DLSQ) Framework. This framework highlighted six interrelated dependencies (Business Strategy; Pedagogy; Process; Resources; Systems Development; Evaluation). The pedagogical effectiveness of this and core organisational drivers needed to help organisations augment their strategic priorities and resources to this framework are discussed. Research findings note that whilst pedagogical effectiveness can be improved by tailoring learning styles to learner preferences, there are other dominant drivers that can also enhance (or hinder) learner effectiveness within organisational settings