One of the first things you need to determine is who is going to be responsible for calendaring dates at your firm. This should be one of your first considerations, because some of the legal calendaring systems currently on the market have not been specifically designed to be used by attorneys, paralegals or other legal staff. Conversely, other programs may seem to be simple and are visually appealing, but lack the sophistication required for use as a true, firm-wide master calendaring system. Some programs may require a great deal of training and experience to use, which will be a problem if you ever decide to change your calendaring model to allow other legal staff, including attorneys and paralegals, to calendar events. Look for software that's easy enough to be used by attorneys and other staff members, yet has all the functionality that may be required by a calendaring department for firm-wide calendaring.
Proper maintenance is essential.
It doesn't matter how many bells and whistles your program has, if everyone isn't using it. Like your documents or billing systems, only 100 percent compliance will result in a successful implementation. Only then will your attorneys begin to rely on it. It must be made clear to all staff members how important it is that all the firm's dates get calendared in the new software. This means that documents may need to be channeled first or copied to designated staff members.