Theres a sequence on our site to properly sync with outlook. Outlook's unique ID's for each contact have caused us some problems.
I would recommend resetting the phone and starting over, or deleting all contacts and starting from there. Sync first with outlook. Then download dashwire and sync, selecting the "The XXX contacts on this phone" check box when prompted after signing in. This will keep all your outlook contacts, delete all your existing dashboard contacts, but then replace them with all your outlook contacts to your dashboard.
Good luck! Check this link out if it still does not make sense for you.
http://my.dashwire.com/help/outlook