Tactical Change Needed
The biggest failing of such companies usually comes down to the manner in which they operate. Because everything is accounted for individually, and every change usually goes through a lengthy and resultantly costly process, the entire IT system usually becomes quickly outdated and inefficient.
Personally I would look at changing the way they do business. Rather than providing funding for indivdual business items piece by piece, and frequently paying through the nose for it, I would be more inclined to contract a number of full time resources. From there on I'd encourage a RAD approach, and keep a seperate data warehouse / accessible demo environment.
Once that's done, work simply needs to be prioritised within the business. Then your contracted workers can go through it within your priority order based on skillsets. You then review how they perform against your expectations / targets.
Too many such companies grow stale and stagnate, idle workers waiting for approved work. Provide the opportunity to set a faster pace and I'd bet the evolution of your IT systems would take on a far far faster pace.
Requirement 1: Competent, intelligent and imaginative skilled staff.
Requirement 2: A desire within the business to adapt and embrace improvements, and keep an open mind to new ideas.
Biting the hand that feeds IT
