Well, if they can't figure out PuTTY, are you sure they are technically proficient?

As for SSH Windows clients, I use SecureCRT. Like ZOC too... you have to pay for them, but they are very simple to use. Data Fellows is decent too.

If you really want them to use ssh, and you have the clout, simply disable telnet/ftp on all boxes.

Another great way to generate interest in SSH, is snooping a couple of logins and passwds and show them to the big boss.