Start with a pilot
Pick five people from different teams — including one with a very large set of files and one who isn't technical. Run their moves first and note every question they ask. That list becomes your instructions for everyone else.
Decide what moves — as a policy
- Which folders are always moved (Documents, Desktop, Pictures)
- Where company files should live afterwards (shared drive or company cloud)
- What is never moved (personal media on work laptops, if that's your policy)
Schedule around the work
Move people in small batches, outside their busiest days. Give each person their new computer with apps already installed, then move their files — that way they can keep working while the transfer runs.
Keep records without invading privacy
IT needs to know whether each move succeeded, not what was in it. Track counts, sizes and statuses — never file names or contents.
Tip
OthTech Switch for Business is planned to give IT exactly that: a dashboard of statuses and verification results, with no access to employees' files.
Don't wipe old machines too soon
Keep old computers for at least a week after each move before wiping or recycling them. It's the cheapest insurance you'll ever buy.