Having worked for one of Boeing's competitors all my career, I am very familiar with their strengths, but also their weaknesses in technical management. But even with perfect engineering and technical management skills and processes, all companies have almost insurmountable problems when trying to make significant modifications to a seven-decade (almost) design: The RATIONALE behind all the design choices are lost to the mists of time. The current engineering staff are settlers, and not pioneers, and the original design history and culture have all died out. So, when all present analysis and current engineering logic indicate that a design change should be made in a certain way, once the change is incorporated and the change put into service, all sorts of snakes pop out of the system because the current generation of engineers don't really understand all the nuances incorporated into the underlying design by their predecessors. Sometimes, a blank-sheet redesign is required. It's the CTOs job to know which is which and to convince management, and the shareholders, as to the proper approach to take. It seems like Boeing may have made a strategic blunder with the MAX when the larger engines were viewed as a feasible modification to an existing airframe. (Blunders are well-intentioned decisions by diligent and well-informed people, but which are nonetheless wrong).