Recently many works have proposed to cast human-machine interaction in a sentence generation scheme. Neural networks models can learn how to generate a probable sentence based on the user's statement along with a partial view of the dialogue history. While appealing to some extent, these approaches require huge training sets of general-purpose data and lack a principled way to intertwine language generation with information retrieval from back-end resources to fuel the dialogue with actualised and precise knowledge. As a practical alternative, in this paper, we present Lilia, a showcase for fast bootstrap of conversation-like dialogues based on a goal-oriented system. First, a comparison of goal-oriented and conversational system features is led, then a conversion process is described for the fast bootstrap of a new system, finalised with an on-line training of the system's main components. Lilia is dedicated to a chitchat task, where speakers exchange viewpoints on a displayed image while trying collaboratively to derive its author's intention. Evaluations with user trials showed its efficiency in a realistic setup.