I've been on one lack of loose coupling project. "All you're doing is importing from here and exporting to there, no problem, right?" and eighteen months later its somehow expanded into touching every part of the business except the vending machine firmware (no, was not a vending machine company). This leads to paralysis where touching anything makes anything and everything randomly crash. This was fundamentally a business process failure in that you can trivially specify a process too big for humans to implement, or even tool assisted humans. However the failure mode of technical debt could have hit a little less suddenly and catastrophically via some technical design decisions (should have jumped off the rails at 6 months and been redirected instead of patching around with the result of exploding at 18 months, etc).
I've been on two lack of refactoring/standardization projects. If you use rails, like back in the ver 1.0 era, you can't just stop updating and do something else, you have a tiger by the tail and if you don't keep up you'll never, ever, be able to catch up ever again. You can't go from 1.0 era to today where today is any time in the last five years. Scrap and complete rewrite. Of course management doesn't understand dependency trees and going back to OS and libraries from 2007 means rolling back 10 years of security patches or hand compiling everything and it would be a lot simpler to just rewrite.
I've been tangentially involved in a poor leadership situation where basically an entire department was forced out by a new leader, taking all their domain specific knowledge with them, and then the consultant friends brought in bled the company dry killing it in a race between expenses of consultants and smelly code being unusable. On paper the company died because of the financial load of switching completely over to outsourcing ("We're not a software company so we will not have developer employees anymore ... but we will have twice as many consultants working two thousand hours per year for five times the pay temporarily")
I've never experienced the parallel development trap, or lack of test suite, those must be interesting.
I've been on two lack of refactoring/standardization projects. If you use rails, like back in the ver 1.0 era, you can't just stop updating and do something else, you have a tiger by the tail and if you don't keep up you'll never, ever, be able to catch up ever again. You can't go from 1.0 era to today where today is any time in the last five years. Scrap and complete rewrite. Of course management doesn't understand dependency trees and going back to OS and libraries from 2007 means rolling back 10 years of security patches or hand compiling everything and it would be a lot simpler to just rewrite.
I've been tangentially involved in a poor leadership situation where basically an entire department was forced out by a new leader, taking all their domain specific knowledge with them, and then the consultant friends brought in bled the company dry killing it in a race between expenses of consultants and smelly code being unusable. On paper the company died because of the financial load of switching completely over to outsourcing ("We're not a software company so we will not have developer employees anymore ... but we will have twice as many consultants working two thousand hours per year for five times the pay temporarily")
I've never experienced the parallel development trap, or lack of test suite, those must be interesting.