A lot of the comments here paint a picture of a dysfunctional relationship with business stakeholders, and then suggest defensive techniques to cover your own a

A lot of the comments here paint a picture of a dysfunctional relationship with business stakeholders, and then suggest defensive techniques to cover your own ass. I understand why one would need to do this in certain situations, but I would also say that your impact and skill growth will inherently be limited in these situations because you're lacking the fundamental thing that cross-functional teams need to succeed: trust. The bottom line is this: exact estimates, especially for large projects are a crapshoot. There is often more than one way to solve a business problem, and long-lived consequences for maintenance, operations and future development. The best solution to large problems can not be arrived at by simply throwing an ill-conceived one-liner prescribed solution over the wall to an engineering team and say "estimate this". What works is to bring a small group of highly skilled practitioners and business operators who have the capability and experience to zoom in and out of the problem space enough to shape a sane low-fidelity plan, and then commission the right discovery and validation to formulate a full plan. This does depend on having the right people in the room and mutual trust between them. It's very easy for one bad apple to derail this whole thing either through outright incompetence or else inability to listen and understand another point of view. Often on HN we paint the picture of the clueless pointy-haired boss making bad decisions, but equally as damaging is the arrogant engineer who is unable to see past their own biases to play out potential tradeoffs with other areas that they don't have deep expertise in.