My team uses Outlook 2016. I understand that the mail server is now at Microsoft / Office365 (having moved from a local Exchange server). We use a shared calendar to track certain deadlines. Each team member creates entries for his/her deadlines, and moves and deletes them as appropriate. Everyone else can see the entries. This is partly due to historical/legacy reasons, and I can't get them to change to more appropriate task management software.

I believe that the shared calendar belongs to a rarely used account (or one that doesn't use the calendar).

I'm looking for a more sensible approach to this, within the confines of the Outlook calendar system. Some of the things that frustrate me are:
I can't quickly view *my* deadlines, among the sea of everyone else's.
I can't put *my* deadlines in another calendar and have them sync with this calendar.

Does anyone have any suggestions? I was thinking something like each team member having their own deadline calendar that is synced with a shared calendar. But it would be important that people (especially our team leader) can view the complete calendar, displaying everyone's deadlines.