Supporting data entry by clinicians is considered one of the greatest challenges in implementing electronic health records. In this paper we describe a formative evaluation study using three different methodologies through which we identified obstacles to point-of-care data entry for eye care and then used the formative process to develop and test solutions to overcome these obstacles. The greatest obstacles were supporting free text annotation of clinical observations and accommodating the creation of detailed diagrams in multiple colors. To support free text entry, we arrived at an approach that captures an image of a free text note and associates this image with related data elements in an encounter note. The detailed diagrams included a color pallet that allowed changing pen color with a single stroke and also captured the diagrams as an image associated with related data elements. During observed sessions with simulated patients, these approaches satisfied the clinicians' documentation needs by capturing the full range of clinical complexity that arises in practice.