What he had done was take a Brand X laptop that was set up with all the updates and applications in place and then smashed the entire old Brand W hard drive contents over the new hard drive's data. It just barely booted into Windows 98.
It took me two more hours to get the laptop functional again.
I learned quite a lot from this incident about ways to involve the users in data transfers while helping them understand what to expect.
One, take control of the user's data transfer experience. If you ask them, "What do you need to back up?" the well-meaning, but uninformative, answer would often come back, "Everything!" I learned to rephrase the question by explaining, "Programs are cheap, mail and documents are expensive," then identifying what they used for mail, where they kept their documents, and then moving data accordingly.
Two, make it clear what I am going to transfer: documents and mail, yes; music, no.
As time went on, experiences such as this one helped pave the way for some positive changes to make the IT staff's life a little easier at our company. Management refused to buy larger servers or entertain the idea of off-site storage, but we requested and received imaging software. Also, easy-to-use, portable backup drives became standard issues with laptop users and power desktop users -- and we set them up to back up selected folders. Machine preparation and recovery time was, thankfully, cut in half.