An observation from working with LOB stuff: Often software is simply the tool companies use so that they can spend dollars to defer fixing issues with training, procedures, or management.
For example, some salespeople have an incentive to over-promise and under-charge in order to make their quotas and bonuses, which causes problems down the line for the company finances and whomever needs to fulfill those requests.
Rather than changing the compensation structure -- or asking the direct managers to do their job with oversight -- the company decides to spend bucks on software, programming the computer to tsk-tsk-tsk and wag an admonishing digital finger. Since there's no followup or moral suasion, a month later nothing has changed except that the sales team has found different "dump stats" for achieving their goals.
Or down the other path where that question is never asked is the madness of 'fully customizable' LOB stuff, like SAP or Domino.
I have that conversation often in the enterprise apps space, and so frequently the fundamental question just hasn't been considered while everyone rushes towards a horrible custom code nightmare that's entirely unnecessary.