Reflective practices are crucial to responsible action. Despite increasing calls for technology entrepreneurs to “be responsible”, very little attention has been given to startups’ reflective practices. Technologies are shaped by the values of entrepreneurs and their organisations and there is potential for both positive and negative impacts of the technologies entrepreneurs are creating. Of particular concern are “dark side” technologies - those that disempower, discriminate and dehumanise; in other words, technologies that undermine, thwart and/or violate our human dignity. This in-progress dignity-centred reflection prototype uses a plurality of ways of thinking about dignity as well as a cybernetic approach to test what reflective practices could look like for technology entrepreneurs who wish to be responsible but are unsure of where to start. Future work will continue to test how centring dignity in reflective practices may provide a fruitful avenue for entrepreneurs responsibly shaping future technology products that value our humanity.