How does the vendor communicate?
Does the vendor use language you can understand? Is the vendor addressing your needs or stuck on sales mode? Is the vendor honest and forthcoming about their strengths and weaknesses? Are the vendor's promises documented in writing? Weak communication skills often indicate weak project management and unmet client expectations, which can turn even the most technically qualified vendor into a poor choice for the project.
Does the vendor understand nonprofit needs?
Consultants who work with business clients will often not understand the dual bottom line of nonprofits, mission and cost. They often recommend expensive solutions built with functionality tailored to for-profits that generate revenue through fee for product or service arrangements. Find out if the vendor has experience working with nonprofits, ask for some examples of nonprofits who have use their tools, find out if they share your values or if their values are in opposition to your mission.
What is the technical expertise of the vendor?
Does the vendor have experience in the technical tools required for your project? Are the vendor's skills and service offerings broad enough and adaptable to changing requirements and upgrades in the future? Do they have examples to show you of products that satisfy your needs? How long have they been in business, how many employees do they have, do they rely on subcontractors for their technical work and if so, for what technologies? Often it is helpful to involve a trusted and independent technical expert to review the merits of the vendor's technical claims.
What is the quality of their work?
Do they have nonprofit clients that will confirm the product works well for their needs? Do they have clients that have used the system for a long time (over a year) or only recent clients . Are the long term clients still happy with the vendor's services and product? The mark of a good large-scale technology project is that it is still serving the needs of the organization a year or more down the road. Too often vendors will provide their latest and most exciting clients, who cannot offer as much insight on the durability of the products and services offered.
Under what model do they provide products and services?
Are they an Application Service Provider (one solution built the same for all clients), a custom developer (product will be built to your exact specifications) or a combination? Do they allow their customers rights to customize their systems, and to what degree? Who owns the deliverables? Do any of the vendor's deliverables require purchasing licenses, how much do these cost and what benefits and restrictions come with each?
Does the vendor's solution match with your needs?
Can the vendor demonstrate how their product matches each of your needs? Is the vendor focused on their product, or your solution - this is especially important to access with vendors who promote one solution with non-customizable features. Does the vendor provide an appropriate level of service, support and availability? Are the products and services provided scaled appropriate for your level of need, or are they too feature rich or feature poor?
Does the Vendor involve you in the Development Process?
Is the vendor able to describe the development process? Are their points in this process that involves the input of the organization? Is there a process for regular communications/meetings regarding progress? Is there a policy and process for evaluating client input and project scope changes? A sound development process will involve the direct participation of the organization project team at several points, from the specifications of the project on paper through the design, development and implementation.