Computer technology and software application evolutions jump at business managers and leaders so quickly now, you almost need a scorecard just to keep up understanding all the changes.  So it is no wonder, then, when major changes are necessary, the entire process can seem daunting and intimidating.  In the areas of new software, Inc. magazine (November 2007) offers some good ideas to keep in mind to prevent technology projects from bogging down.

Among the suggestions and issues to watch for:

1. Do not start with a mediocre team of developers.  Designing software is hard work.  Make sure you are utilizing proven and experienced people who have verifiable credentials of success.  Mediocrity here is the number one cause of software project failures.
2. Weekly Milestones.  Because developers are building something that hasn't existed before, widely spaced milestone intervals could indicate that they're not considering all of the details that need to be implemented.  Any spans longer than 2 days should be suspect.
3. Negotiating the Deadline.  The process is the process.  If it is going to take 90 days, don't demand it be done in 40 because this will allow "split-the-difference" thinking to creep in.  you will end up meeting the deadline, but not getting what you contracted to get.
4. Dividing Tasks Equitably.  Because of the creative aspect of software programming, reassigning already started work to others adds considerable time to the process while the new person gets up to speed.  Expect slow downs and problems if you choose this route.
5. Work till Midnight.  A lot of research exists showing that working more hours does not produce software any faster.  this is due to the intense creativity brain drain that occurs in developing the program.  Even the best programmers cannot sustain more than a few hours per day of intense efforts.  Realize this because it is built into the timeline already.

I would add a final thought.  Hire a well researched and respectable partner to do the work.  Outline your needs, review their proposal, and then get out of the way and let them work.  Review the planned milestones, but once the agreement is made, know that the process will take that long. 

Having been involved in 4 major software development programs (I'm nowhwere near being an IT guy), my best results came from remaining vigilant, but in trusting the experts to deliver on the agreed upon deadlines.  Don't micromanage them; just expect the promised results.