At the start of the cloud migration, the plan made sense. The sequence was clear, responsibilities were defined, and the work was broken into phases that felt manageable. People left planning sessions with a shared understanding of what would happen next.
That clarity didn’t last.
As work began, dependencies surfaced that hadn’t been fully visible during planning. Teams ran into constraints created by other initiatives already in motion. Assumptions about timing and sequencing started to break down. None of this was surprising in hindsight, but it was destabilizing in the moment.
The initial instinct was to protect the plan. Deviations were framed as exceptions, and there was quiet pressure to “get back on track” quickly. The risk was that emerging reality would be treated as failure rather than information.
Instead, the team leaned more deliberately on iterative planning and regular retrospectives. These weren’t used to reassert control, but to make sense of what had actually changed. Each cycle created space to revisit assumptions, surface new constraints, and decide what still made sense to hold.
The conversations weren’t always comfortable. Some surfaced mismatched expectations across teams. Others revealed frustration about work that had started but couldn’t yet be finished. What mattered was that these discussions happened while there was still room to adjust — before trust eroded.
Over time, planning began to feel less like a contract and more like a hypothesis. The team stopped expecting plans to survive intact and started expecting them to evolve. Adaptation became routine rather than disruptive.
The work didn’t become predictable, and coordination remained challenging. But trust held. People had a shared way to talk about change without blame, and a steady rhythm for deciding what to do next based on what they were learning.
Insight: treating plans as hypotheses preserved trust and momentum when reality shifted. Instead of forcing adherence to outdated assumptions, the organization maintained alignment, reduced friction during change, and kept the migration moving forward without turning adaptation into a loss of confidence.