When an old coffee grinder stops working properly, it endears itself to the author by seemingly trying to get itself going again—revving its motor as he continually presses the start button until it gets back up to regular grinding speed. This affords a potent little design lesson: sometimes a product’s shortcomings create opportunities to bond with a user. In the case of conversational design, a chatbot or intelligent digital worker (IDW) can make overt attempts to solve problems outside its abilities, just to let a customer know that it’s trying its best to help. Even though the IDW can’t deliver the desired outcome, before it passes the interaction on to a human agent, it can create an enduring sense of empathy that will carry forward