Bobby, you’ve touched on a sore spot for me with regards Outlook and mobile.

In our organisation we use Outlook (2003 – not that it particularly matters) on our desktops and iPhone 4’s. No problem picking up mail etc whilst out and about on the iPhone but the problem does arise when you’re using some kind of system to organise/prioritise your mail – whether that be GTD or any other process of choice.
I am currently using a simple system which is a Frankenstein’s-child of GTD, etc. Bear in mind that I generally work at the desktop Mon-Fri 9am-7pm. Let’s imagine that I stick to the principle of processing inbox emails twice a day (although in reality I check more often than that but have turned off all notifications other than the New Mail icon on the system tray, and ignore anything that can wait for the next batch of processing).

I simply mark them as read and flag them with a coloured flag depending on which “bucket” they are due to reside (Red: Me to do | Blue: waiting/deferred | Yellow: Someday/maybe | Green: ready, although I’m not too sure what I intended that last one to actually cover!)

HOWEVER, on the iPhone you cannot see/create a flag – which means that when away from the desk I can’t operate the same processing rule.

I’ve been looking at using tools that build on Outlook – clearcontext.com being a good example. But when taking into account the iPhone’s limitation I can’t have a consistent approach which would be especially hampering if using a tool such as this due to the wider-ranging changes it makes to operate the system properly.

Anyone got any thoughts or experiences of tools that do work – bearing in mind the necessity of having OL on the desktop?