Nobody walks into a retail system implementation expecting it to fail. The budget's approved, the vendor's been selected, the kickoff meeting has coffee and optimism in equal measure. And yet, somewhere between that first meeting and go-live, a lot of these projects quietly fall apart — not dramatically, not all at once, but in the slow, grinding way where timelines stretch, costs balloon, and the system that eventually launches is a shadow of what was promised.

I've seen this pattern repeat itself across organizations of very different sizes and sectors. The common thread is almost never the technology itself. It's the decision-making that surrounds it — how the system was selected, how the rollout was planned, how change was managed, and whether anyone with real retail technology strategy experience was in the room when the critical calls were made.

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