In recent years, technology has played an increasing role in many sports, including swimming. Far beyond the stopwatch and hand marked events, detailed biomechanical attributes can be measured using technology such as instrumented blocks, wire tethers and underwater/dolly cameras. With the advent of micro-technology, there has been an increasing trend toward the use of wearable sensors such as heart rate monitors, cadence aids and - more recently - activity monitors. The micro-electromechanical system (MEMS)-based inertial sensor class of activity monitor is of particular interest to the CWMA (Centre for Wireless Monitoring and Applications) at Griffith University. Due to the intensely competitive nature of professional sport, the difference between winning and not winning can be as little as a few hundredths of a second. An improvement to any single physiological or psychological parameter could potentially give one athlete a 'winning edge' over his or her competitors. This paper provides a context-driven needs assessment to illustrate the use of technology in various situational contexts related to swimming. The end goal is to improve training outcomes by allowing the strategies and requirements of stakeholders to be targeted.