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Importantly there is no right or wrong answer to these questions, and answers may vary greatly from one vendor to another. There are however some answers that should throw up a red flag:
Question 6 - This is generally a good guage of customer satisfaction. If vendor can not provide this information, or is not willing to do so then you can anticipate a support issue or poor customer satisfaction with product.
Question 10 - You should always have ability to get to your own data. If you require a programmer to build new reports then you will consistently be biting into your ROI.
Question 14 - If vendor skirts around this issue then they are uncomfortable letting you talk to a recent customer and therefore maybe hiding something from you, perhaps a difficiency in their product or in their implementation process.
Question 15 - The answer to this question identifies how 'productised' software is. A vendor who regularly evaluates their customer's future requirements and spends money on building these into their product is committed to it's current customers. A vendor who spends money only 'as required' is probably not so committed to building a great product as they are to getting sales.
When getting answers to these questions please also consider that their may be legitmate commercial reasons as to why a question can not be answered, however at a bear minimum your vendor should be able to provide some background into their reasons for not answering.
There are another four important criteria upon which any experienced buyer will evaluate a software purchase which will be covered in future articles.
Jay McCormack has had years of experience in the web and software industry. Most recently he launched http://www.cheaperit.com where he reviews and recommends the best software found on the web.