Here, I discuss lessons learned relating to contracts and contracting:
When bidding on projects, try to involve selected individual developers and other technical personnel deployed on other project teams. They can supply useful lessons learned based on other relevant projects from your organization. In addition, they may be in a better position to determine whether the proposed cost and schedule are reasonable for the functionality requested in the RFP.
When producing estimates for the project, have at least two people estimate the time and resources for the project independently. If the estimates vary widely, determine why.
Consider providing a probability figure with the estimate. Applying the "50% rule" described earlier produces a valid estimate. But what if you want to bid a more aggressive estimate to win the business? In other words, some contractors bid low knowing that they will take a loss on one project so that they can win business with a new customer. In that case, it may be worthwhile to produce two estimates. The first estimate follows the "50% rule," and the contractor gives the customer the second estimate to win the bid. The difference between these two estimates is the estimated exposure the contractor will have to absorb if the more aggressive estimate doesn't work out. The contractor's business organization needs to know this information to prepare for a possible overrun.
Consider computing and tracking Earned Value to help determine if the project continues to focus on the right activities as defined by the contract. Be aware that this requires tracking staff hours at a lower level of granularity than the level to which you may be accustomed.
