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This paper focuses upon a critical aspect implicit in C West Churchman's Hegelian Inquiring System, namely its ability to provide all the necessary ingredients for the emergence of a learning culture. This focus is achieved by articulating certain phenomenological aspects of the Hegelian model. In particular the relationship between subject and object is explored. After its emergence the learning culture then requires a special kind of thinking, which results in certain capacities, to continue its evolvement. This kind of thinking has been defined as Perspectival Thinking and is elaborated in the context of an Information System as a social system bound to technology. In the absence of a learning culture no organization can sustain its learning capacities, yet how often are learning cultures taken for granted? This paper explores a number of ideas that provide the ground for developing and sustaining learning cultures.