Misconfigured backup client: While it's vital to have some sort of backup for staff who don't frequent the office, a misconfigured backup client can wreak havoc on the performance of off-site employees. Where possible, closely identify which file types will be backed up, as well as where they should be stored, and communicate that policy to staff.
Windows updates: The problem happens when your CEO checks into his hotel, powers on his laptop, and gets Windows XP SP3 forced down his throat. The orderly distribution of updates can be done in a more friendly way via Windows Server Update Services. Alternatively, group off-site workers into an Active Directory Organizational Unit that has a relaxed set of update policies.
Lack of a plan B: You'll eventually get a call from the most important person, at the worst possible time, telling you she can't connect to the network. Whether it's a VPN client issue, network connectivity, corrupted application--whatever it may be, have a backup plan. If a VPN client bombs, can you serve out a remote desktop? If a hotel's network is problematic, can the employee tether a smartphone to the laptop for Internet access? If Office gets corrupted, can you deliver an online version through Citrix or Microsoft Terminal Services? If you can plan ahead for disaster for your road warriors, you'll thank yourself later.
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Five Ways To Arm Your Mobile Workforce