Ok, so I am the only one in my office with any form of tech knowledge, and I am sketchy at best.
I have an android, my boss has an iphone. I use google calendar for tasks, contacts, and we have a POP e-mail system. The phone syncs everything over the air, and I have no complaints with it.
My boss wants to have the same luxury with his iphone, but he uses outlook for everything, and won’t give it up. I know you can sync the iphone with the outlook calendar and contacts through itunes by pluging it in, but he is never at a computer.
Is there some way to have the iphone setup like my android while using outlook? Automatic over the air updating without plugging it in? What am I missing here?
Setup Outlook to delete emails after 1 or 2 days in the Advanced options for his POP account. Setup his iphone to receive emails from the pop server and never delete. This will only work for new emails obviously - if you need his old emails synced you should see about using imap
You really need to at least move to IMAP if it is too small for Exchange or just switch to Google Apps for your outlook/calendars/email. POP is horrible and you are really asking to lose some emails when you throw multiple devices into the mix. Just my 2 cents.
You are trying to do new things on old protocols. Outlook calendars rely on either a protocol server running or exchange. Setup a new server and use that, pay me to convert you guys over to Google apps and integrated solutions, or just use your iCloud account for your calendar. You can view it on phone, web, and also add it to your outlook.