• How much of her own time would an executive be willing to spend each week to get some feature or analysis? If she's not willing to do it, who else can?

• How much housekeeping by users is really required for good system operation? Gauge the number of minutes per day that users will spend on administrivia. It better be about zero. (In one recent customer engagement, a CRM system was generating thousands of internal administrative tickets a month before the system was used by 20% of the employees. Yikes!)

The Large Print Giveth, and the Small Print Taketh Away

Taking my wisdom from Tom Waits: When you choose a CRM system, you don't know about all its "small print" issues. You also don't know how the users will adopt the system, or where they'll perceive value.

So it really pays to do some introspection on the "soft issues" surrounding the CRM direction, because they'll be the basis for several hard realities a year or so later.