I agree deadlines are a necessary evil to ensure we hold ourselves accountable to both customers and internal non-eng stakeholders who need to know when things will ship in order to make plans around them and collaborate with us effectively.
One approach to develop a healthy culture around deadlines I've been thinking about lately:
Plan the deadline around the minimal lovable product, while spec'ing out the minimal shippable product, and ensure there's enough of a delta between the two so we can have a large degree of freedom w.r.t. scope.
Without this freedom to vary scope, _when_ (not if) our estimates invariably fail, our only options would be to extend the deadline (defeating the purpose of setting deadlines in the first place if we resort to this often enough), or to burn ourselves out with overtime work in an attempt to meet those deadlines (obviously results in an unhealthy/unsustainable environment, and not even guaranteed to succeed).
One approach to develop a healthy culture around deadlines I've been thinking about lately:
Plan the deadline around the minimal lovable product, while spec'ing out the minimal shippable product, and ensure there's enough of a delta between the two so we can have a large degree of freedom w.r.t. scope.
Without this freedom to vary scope, _when_ (not if) our estimates invariably fail, our only options would be to extend the deadline (defeating the purpose of setting deadlines in the first place if we resort to this often enough), or to burn ourselves out with overtime work in an attempt to meet those deadlines (obviously results in an unhealthy/unsustainable environment, and not even guaranteed to succeed).