What is the biggest mistake I see in new IT outsourcing deals? My answer is simple and direct: the failure to provide continuity from contract conception to execution.
Remember the movie "Charlie Wilson's War"? There is a scene where Charlie is sitting with his contemporaries asking for additional black funding to help Afghanistan rebuild after the Soviet occupation and successful U.
S.
covert operation there.
Well, the answer was that nobody cared enough to follow through and insure Afghanistan wasn't a problem in the future.
It reminds me of the outsourcing selection and contracting process.
We have expensive legal help, executive help, outside advisers, a virtual village when we are building the deal, only to oftentimes hand it off to a separate group of practitioners and governance professionals who simply do not fully appreciate what was contracted.
What's even more amazing to me is that sometimes you will see the purchaser do the same thing! This can be avoided by building a "contract continuity" plan that helps to insure the spirit, terms, and goals of the deal are fully executed by both parties when the deal is done.
Here are some key areas to look at in your "contract continuity" planning process:

1. There should be no less than one executive/manager from teams, the provider, and the purchaser who will participate in the execution of the contract operationally and who are also central participants in negotiating the actual deal.
   These people will represent not only the written contract for interpretation, but will also be tasked with keeping the spirit of the deal alive as well as keeping in mind goals and objectives as defined by the contracting teams.
   
2. The provider will ultimately pick an account manager - this person should be involved in contract negotiations from the beginning.
   The selection of this person is key, and every effort should be made not to let that person transition away from the account.
   
3. Plan for "operationalizing" the contract - the process for planning how the relationship will be administered.
   This top to bottom planning process should cover all points from the organization of your retained team to how a work order will be processed and executed.
   
4. Progress to goal reporting should be considered from day one of the contract.
   There should be a standing agenda item for all governance meetings for both the provider and the purchaser to review the original goals of the contract, and the progress against those goals.
   Staying in touch with your original goals often in the governance process will either validate your success or give you a pivot point from which to change plan and direction.
   

These are a few suggestions to get you thinking about how challenging of a task it is to make a contract operational.
The fact is, the effort you expend in the critical first months of the contract maintaining the continuity of the original deal will pay dividends for the life of the deal.