I have it easier than many because my "customers" are generally the employees of our company, so it's easier to set and manage their expectations. Regardless, it still needs to be handled delicately to minimize their upset and resistance to change.
I think a few key factors really helped in the process
- (Self evident) Let everyone know what to expect out of their experience during the transition
- (Self evident) Work around the customer's schedule. In practice this meant scheduling downtime for our 9 to 5 employees from 8pm to 6am and scheduling downtime for restaurant managers from about 2am until 8am
- Be honest about the fact that you'll run in to problems and fix them immediately
Finally, I have to give Microsoft props for ensuring that Outlook 2007 will automatically recognize the new 2010 server without any user action. For our office users, this should make the transition go essentially unnoticed.
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