Any way you do it, upgrading an organizational website to a new major version of Drupal - for example, from Drupal 5 or 6 to Drupal 7 - is a significant task.
Change can often be a hard thing for groups—even progressive groups. Getting a staff team to willingly adopt new software or a new website can be challenging. Especially for staff who always feel a shortage of time in getting the important work done.