The automation and systemisation of the next generation of cognitive assessment approaches have the potential to change how clinicians assess and interact with patients. This may be especially pertinent in the case of delirium, as current methods often rely on the subjective opinion of clinicians and specialists, with potential for the condition to be overlooked or misdiagnosed. Currently, one of the most commonly used tests, is the clock-drawing test, which has relatively wide appeal as a cognitive screening instrument due to its clinical utility and psychometric properties. However, there are a number of inconsistencies associated with its use and interpretation. In this paper, we describe a new assessment methodology that we have developed, facilitated by the advances in tablet technology. In trials, our "Letter and Shape Drawing (LSD)" tool, involving both an automated scoring capability and a simpler user interaction, has demonstrated correlation with other conventional cognitive test methods although some optimisation requirements remain.