As technology becomes smarter and smarter, designers are faced with a dilemma … do we make decisions on behalf of users, or do we advise users but leave the decision up to them? Automation is inevitable, but what is the responsibility of a designer to automate decisions for users? If our lives become more automated, what happens to us as a society. In this talk, we explore automation with examples from the auto industry and the impact of robots in factories as well as auto-pilot in the aviation industry and the phenomenon of “de-skilling” as pilots are losing their ability to react and respond when crisis occur. Automation is unavoidable, but as designers, we need to find the balance between automating decisions and anticipating decisions on behalf of our users.