How do i configure SBS premium edition to send copies of mail(intra/inboud and outbound) mails of an individual client to either his webmail or a thrid party email address?

We are in the process of installing a premium edition of the SBS, one of the senior managers insist that he would like to always get a copy of all mails sent to his office outlook copied to his yahoo account and for intra mails(where he get copied on any assignment) also have same sent to yahoo & his web mail.

I have given him the OWA option(for all intra & external mails) but he specifically called for the routing mentioned above. Please, is this posssible in both standard & premium edition? If Yes How?