This paper takes a contextual view of “searching as learning” to examine what it entails within the context of workplace learning. Given the intertwined nature of digital technology with any aspect of work in the current workplace, this research asks the question – what does it mean to search for information in relation to learning? Using field study data from a study of IT professionals working in the area of information security, this paper conceptualizes searching as learning as having two components: problem solving which involves the purposeful search for information that assists with problem at hand and exploring which supports knowledge building for broader skill development largely targeted towards the future. Within both these activities that constitute searching for learning, the use of digital resources plays a key role but so do interpersonal relationships. To be effective, professionals reported being adept at utilizing both strategies. This is particularly true in the IT profession where skills requirements are highly dynamic.