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Planning and executing any type of organizational change must begin with an understanding of and respect for the office culture. This can be especially difficult in environments where the culture is resistant to change. Often, higher-level managers will find lots of excuses for not making a change, usually couched in the triple constraint: The change will be too expensive, time-consuming or out of scope.
To begin the change process, especially if the change involves moving from a traditional Waterfall methodology to a more iterative or Agile approach, a project manager must be ready to counter the objections related to the triple constraint. Sometimes, the best way to do this is by example: Use a small, non-mission-critical project as a proof of concept. Measurable success using an iterative approach on a small project can go a long way toward organizational acceptance.
It is important, not only to start with a small project, but also to start with small changes. Rather than adopting a new Agile methodology, it is easier to introduce an iterative approach. For example, instead of instituting Scrum with its ceremonies and artifacts, why not try organizing the development and testing into sprints? Scrum-but isn't necessarily a poor excuse for Scrum; it can lead the way to adopting Agile development.
Finally, it is helpful to find an "angel," a senior-level executive who is not resistant to change and is open to and supportive of Agile or the iterative approach. The angel will be the senior manager who gives the go-ahead and supports the proof of concept. Resistance to change within an organization comes from change-resistant people, and when change is supported at the highest levels of management, eventually those who are resistant to change will buy in or leave the organization.
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