I’ve seen two predominant ways that project plans get created in my IT experience. In some cases, stakeholders barrage the team with a set of feature demands. This often results in plans where the details are over prescribed and more important priorities (especially modernization) get missed. In other cases, IT organizations and stakeholders don’t engage deeply enough with each other to truly understand the business drivers and what their highest system enhancement priorities are. In both cases, the remedy you often hear espoused is that IT organizations should “partner with the business.” I never quite know what that means. The first group of stakeholders just wants to tell you what you should be doing, and the second is probably so busy with their own troubles that they have no interest in “partnering” with IT. In both cases, the call to “partner with the business” can tend to fall on deaf ears.

Instead, I believe that the right approach is to drive alignment between IT and stakeholders through creation of a clear vision, roadmap, resource plan, and metrics of success. The vision must articulate precisely how technology will help deliver on the mission of the organization. It should create the bridge between stakeholder business objectives and technology investments.  It must be described clearly enough that you can read it and know immediately what the team wants to build and how it will help the business vision. In short, it must be that perfect balance between aspiration, forward-looking and specific, described in language that resonates to both stakeholders and technologies.

I’ve often gotten feedback that “the stakeholder doesn’t have a clearly articulated vision for us to work from.” In those cases, it’s the job of IT to create a strawman and present it to stakeholders saying “This is what I think the vision is. Help us refine it.” 

Part 2. Organize Around the Work and Keep the Organization Flat
Part 4. Connect the Vision to a 2- or 3-Year Roadmap but Embrace Agile Development

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