Every CRM rebuild we take on starts with a confident estimate and ends with us writing migration scripts at 11 p.m. We keep underestimating the same three things — none of them are technical.
First: nobody knows the real schema. The "current CRM" is the official one plus three Excel files plus institutional memory. We now spend the first week mapping the unofficial system before we touch a database.
Second: history is non-negotiable. Sales teams want every comment, every status change, every email — even from records nobody has touched in five years. Plan migrations around full provenance, not "minimum viable data".
Third: the cutover weekend is a myth. We schedule a parallel-run period now — both systems live, writes mirrored — and only flip when the team agrees. It costs a sprint. It saves a launch.