Plans become obsolete within weeks, but the act of planning together creates shared understanding that lets teams pivot when priorities shift. The CRM rollout succeeded not because the plan was accurate, but because planning built alignment.
Your roadmap is fiction within weeks of creating it. Priorities shift, leadership changes direction, and that feature everyone agreed on in Q1 feels irrelevant by April. But here's what actually matters: it's not the plan that saves you, it's the planning itself. The author learned this launching a massive CRM overhaul where the original plan changed constantly - they reprioritized features, adjusted timelines, shifted rollout sequences - yet shipped successfully because everyone shared the same mental model of what they were trying to accomplish.
The difference shows up starkly in two projects at the same company. The CRM rollout worked because the team did the hard work of planning together: they named assumptions explicitly (regional leaders need to see pilot value, IT security will approve, salespeople will engage with testing), built in decision points to reassess those assumptions, and created a common language the whole team understood. When technical delays threatened the timeline, they didn't panic about the schedule - they asked which assumption was at risk and focused energy there. The dropdown project failed because they skipped planning fundamentals and jumped straight to implementation details. Three senior leader meetings debating what options should appear in dropdown fields, and when they finally launched, no one used it. They'd never established what problem they were solving or whether users actually wanted it.
Good planning creates three things individual plans can't capture: a common language so teams stop rehashing the same debates, explicit assumptions you can check when things change, and surfaced conflicts before you're mid-sprint with no time to resolve them. The practice that saves teams most often is writing down what has to be true for your plan to work - not hopeful things, but actual dependencies. When something changes, you know which domino fell. The CRM team planned the first pilot group in detail but kept the full rollout deliberately fuzzy, which let them adjust based on what they learned rather than forcing them to stick to assumptions made months earlier. Planning everything in equal detail creates the illusion of control while actually making you less adaptable. Your plan will be wrong, but planning gives you a team that can pivot quickly because they've already wrestled with the hard questions together.
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