For years I've tried a bunch of different methods to keep my personal and work calendars synced. My companies insists on using Outlook/Exchange Server, and I prefer Google Calendar because I can get it on all my devices. Most of the time my personal and business schedules don't overlap, but on the occasion they do, I want to make sure both calendars reflect my schedule.
So here is what I do. It's a two step process, but it only takes a few seconds.
In Google Calendar, when creating an event, make sure to add you Outlook user email address in the box provided to the right of the event details.
Once you save this event, an email is sent to your Outlook email with a calendar invite. Just accept it in your Outlook calendar, and there you go, you now have the same event items in both calendars. And the nice thing is, when you make an update to the event, it's pushed to all those who are members of the event.
Low tech I know, and takes a few steps, but no messy sync systems or paying for services.
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