At a previous job, I was tasked with automating an industry that had not seen much automation at all. I was told that we had someone in-house who "knew the industry" and "could be used as a resource", but this person was only ever on one side of the transaction, and that side wasn't the majority of the process we were trying to automate (it was like trying to computerize a retail checkout process and your "expert" was someone who had only ever waited in line to pay).

When I said I'd like at least a month to actually go and do the jobs of the people and companies in the target demographic, I was told we didn't have time for that.