We present a strategy to privacy aimed at stimulating the adoption of privacy-preserving behaviours when sharing images online, with the intention to overcome the so-called privacy paradox. Through a socio-technical approach to privacy, we use design as an actor of change and privacy enhancing technologies as enablers of change. Building on Gordon Pask’s Theory of Conversations, we design an experiential dialogue between people and algorithms to understand what factors impact self efficacy in protecting personal information contained in image data. Through this dialogue we engage participants in thinking abductively to assess their awareness of privacy risks across their past, present and future. Hence, this dialogue becomes a platform to observe participants as a system of reactions to the stimuli developed from conversing with algorithms, and to understand whether these stimuli would trigger any proactive behaviours. Our approach reframes the analysis of human and technology relations through behavioural elements, with the ambition to favour a more inclusive privacy communication.