I am very frustrated with Microsoft Outlook - particularly the calendar... which, for every scheduling / meeting exchange, requires one to switch between inbox and calendar. As a calendar fills up, this becomes more and more cumbersome - and ineffective. It is a root of daily pain - and for those around me, complaining. So I posed the question to Facebook and Twitter: what are great examples of plugins that make Microsoft Outlook more efficient / effective:

Here is the solution I have gone with (at least thus far). It shows just how frustrated I am - since it is a lot of work - and, to Jon Steinberg's point above, it shows the role Google plays in all of this:

1. I set up a sync for my Outlook Calendar with Gmail. It works both ways and is quite easy to set up (see here).... I wish they did this for contacts too!

2. Using Google Chrome, I installed the Google Calendar Checker w/ Popup. It displays your calendar as a Chrome extension and shows appointments, dates, etc all within a drop down.

This works great if you use dual monitors and have email and browser on separate screens. It's better than Outlook on a single screen (even this small laptop) - but is still not ideal. At least it allows you to navigate the calendar (particularly by date) without having to lose your inbox position.