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IT outsourcing: 100 questions for a successful engagement

Patricia Ensworth | Aug. 16, 2010
Project management plays a critical role in outsourcing.

FRAMINGHAM, 13 AUGUST 2010 - When headcount and revenues shrink during a recession, executives often try to keep operations stable by controlling IT costs. Although they may have shunned the practice in the past, many midsize companies and government agencies are for the first time considering outsourcing out of necessity. For CIOs at these organizations, the prospect of outsourcing IT can be daunting because their performance will be evaluated by an entirely new set of criteria.

A wealth of data, case studies, consultant advice, and peer-to-peer war stories exist to help organizations make outsourcing decisions. But once the decision is made and it's time to transfer responsibility for corporate IT to the vendor, the CIO is in the hot seat. That seat can grow even more uncomfortable once the CIO realizes that, to a large degree, the success of the outsourcing initiative depends upon the skills, knowledge and creativity of the project managers on the front lines of the engagement.

Project management plays a critical role in outsourcing. Many organizations now track outsourced labor and expenses in enterprise-wide project management systems. Unless the IT project managers understand the challenges and success factors associated with outsourcing--and how they differ from those associated with in-house development and operations--the CIO's key performance indicators may unnecessarily turn the wrong color.

The checklist on the following pages can help CIOs and project managers ensure that their first outsourcing projects are managed wisely from start to finish. The 100 frequently asked questions (FAQs) listed on pages two through five address the organizational, technical, and team leadership issues that every project manager should anticipate and proactively tackle. The questions are organized by project lifecycle phase to facilitate alignment with project tracking systems. They are also categorized by the three principal roles a project manager plays: the Entrepreneur, who focuses on senior management's business priorities; the Technology Partner, who collaborates with other professionals to optimize the solution; and the Team Captain, who supervises the workers. There are also a few questions in a Guru category. In addition to helping guide project managers, the questions can also help CIOs identify the right project manager within their organizations to lead the outsourcing initiative.

The answers to the FAQs will vary depending upon the type of business, system, team structure, and risks involved. No matter what your software functionality or engineering methodology might be, these are the critical questions the CIO and project manager should ask--and ask early--otherwise these questions will definitely be asked later during the forensic analysis of the dysfunctional engagement.

Phase 1: Initiating


1. Why are we doing this? Why now?

2. Whose decision was it?

3. What are the success criteria?


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