I'm planning a new workshop on selecting donor databases, focusing on the question, "Why is this so friggin' complicated?"  Some initial thoughts:

The maxim "Fast, cheap, or good--pick two" is true.

You want the technology to be forward-looking but also want to avoid shiny object syndrome.

You want to make a reasonably quick decision but also need to get input and buy-in from stakeholders.

You want to think big but don't want to neglect operational details.

The system needs to be intuitive for fundraisers but streamlined for data entry. 

It needs to be easy to get reports from the database but it also needs to support complex selection criteria.

How can you know what you don't know (e.g., what a new database can do when you only know what your current one does--or doesn't do, what you'll need in the future)?

There are literally hundreds of choices. How do you get down to one?

Have you experienced this "analysis paralysis"?  How have you solved it (or have you)?

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What the Customer Wanted