My roommate's looking for an entry-level IT gig in the San Francisco Bay Area, and it's my job to make sure he's got the necessary hands-on experience to feel comfortable taking on a job as a jr. systems administrator or working the helpdesk.
He's got solid troubleshooting experience with Windows XP, he's done some work installing and fixing issues with both Office 2007 and 2010, he's got a little bit of experience on Windows 7, and he's custom-built several PCs for clients. I had him research parts, price them out, create invoices, and work with the customers to purchase everything, so he'd get a good feel for the operational side of IT as well as the techie-work. (He's been horning in on my side-work, dammit.

) He's also done some work setting up small-office routers, (a couple of Cisco-Linksys and a Netgear,) and he's got a couple of certs under his belt: A+, Network+, and Security+, all of which I made sure he studied honestly for and did as much hands-on work with as time and budget allowed.
Now that he's getting ready to find some full-time, formal work, it's time to do some more extra-curricular lab-work so he feels ready for whatever gets thrown at him. He's studying for
70-680, and I'm going to work with him in the following areas over the next month or so:
- Configure a trio of Cisco 1721 routers running IOS 12.4T with proper IP addresses/subnet masks on appropriate interfaces, host names, etc., and then make sure they can ping each other by setting up static routes and maybe even RIPv2. He's also going to learn some of the common 'show' commands, and what they're good for. (Just enough so he won't freak out if he's asked to hop onto the IOS on the job.) I've also got a SonicWall appliance and a Cisco PIX 501 firewall for him to set up and tinker with.
- Install and configure a Windows Server 2008 R2 box as a domain controller, (with a Windows 7 VM as a client,) as well as set up basic DHCP, file and printer sharing, and do some fundamental group and user practice, (setting permissions, resetting passwords, enabling/disabling accounts, etc.)
- Install and set up a vSphere box, then spin up some VMs, just to make sure he's familiar with how virtualization works and how to tweak the resources for each image.
- In our area, Symantec Endpoint Protection is pretty popular, so I'm going to have him download and install a trial of the SEP11 server so he can install it and practice deploying clients, as well as updating definitions, and the like.
- Again, Symantec's the hot seller around here, so we're going to do a trial-install and basic tinkering with BackupExec as well and make sure he knows how to both set up back-up jobs, as well as restore data with it.
- We're going to set up a SpiceWorks box so he can get a feel for how ticketing systems work, (and I could use the practice of setting it up as well.)
- And finally, he's going to snatch up some of my training material on a couple of Office 2010 programs that he could use some more experience with: Excel, Outlook, and PowerPoint; learning Visio probably couldn't hurt either.
- (I would have him start messing around with Linux, but he's got a pretty full plate already, and I haven't seen a whole lot of entry-level positions ask for Linux skills around the Bay Area. He does want to eventually learn about it, and possibly pursue Linux+.)
I don't expect to make him an expert, I just want him to feel prepared for the work-environment he'll be dropped into as a helpdesk tech or a junior-admin. Any other suggestions on things he should be looking into learning before the plunge so that he won't feel completely lost?