Observation is a key skill in performing analysis and evaluation activities during development and maintenance of an information system. This paper looks at how this skill can be learnt by investigating the research question: “Can observation learning be improved by introducing a meta-observer?”. This research consists of using a simulation of a real life situation of an observation scenario embracing three different roles: a user, an observer and a meta-observer. The user, while performing a task, is encouraged to ‘think aloud’ by the observer. The meta-observer’s task is to observe the observer and to provide feedback. Findings in terms of strengths and problems concerning the role of the meta-observer are presented.