Still gathering requirements...
First have a really clear Idea what your client is expecting from this guy.
Then probe him on exactly what his role has been on similar deployments. Also make sure he has been migrating off the same legacy operating system that your client has. IMHO the problems will come from the legacy end rather than the Win 7!!
Remember - If he has been in a big organisation there will probably be at least a dozen people that would claim to have been the lead techie on it.
Last edited by yorkshireman; 30th November 2010 at 12:10.