Encrypting emails - for dummies

I am looking for recommendation for any third party email encryption applications that some of you may be using out there. The scenario is that management wishes to be able to encrypt various emails to each other. As of right now, we are looking at about four people who would be doing this. They are all running Outlook 2007. This product needs to be so easy to use (management), that even a caveman could use it. Minimal amount of additional steps required.

Hexagon MiningAsked:
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MadjaxConnect With a Mentor Commented:

Look at this one: http://www.pgp.com/products/desktop_email/

I know many banks & insurance companies run that one, at least in my country
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