Here's the story,

A large part of my companys work involves travelling alot in city/rural environments.
due to the nature of the work the staff are often in situations where they are lost or are in need of directions.

As you can imagine trying to give directions over the phone when you have no idea where they are actually are is quite hard.

Heres the Question:

What is the easiest way for staff to "share their location" so an operator from a central location can track them and give directions.
Is it possible to load 'places' into google maps/earth on the HTC?

I have done some searches and I get mixed results from everywhere I look.
Any help would be apreciated.

Cheers!

They can use the 'My Location' feature of Google Maps for Android, take a screenshot and e-mail it to the office. Sounds easy, but it may still be too complicated...
You can also modify google maps to suit your needs. Some programming is required, but it is not that complex. Have a look at this page about Google Maps API.