For the presentation itself, if possible, ask each supplier to structure their presentation in the same way. For example, an initial few minutes on the supplier, then a demo of the software, and then Q&A. And within the demo, it can be useful to ask each supplier to show how they would approach a set of the same requirements. Thus, if there are, say, half a dozen specific issues which you want to cover and ensure the software supplier can manage for you, then ask to see how they would approach them. This way, you can see clear differences (or similarities) as to how each supplier works and you might well learn some interesting and different thoughts and approaches along the way.
Of course, you need to allow for some flexibility. Some suppliers might suggest they initially give you an overall picture of the software before showing you individual elements which you have asked for, and that is probably fair. After all, you aren't trying to trick them, you are trying to ensure the software is right for you, and if that is the way that the supplier thinks is best then let them do it. And if they then veer off-track and simply don't follow you requests, then you can consider whether that is a black mark against them for the whole process.
When it comes to questions you could ask the suppliers, then of course you will need to cover at least the functionality and/or services you are looking for. But there are many more questions you could ask which could help you and give you an insight into the supplier, their solution and their whole approach. The following are some of my favourites which I have built-up over the years:
• What doesn’t your quote include? [This is an interesting and useful question as it should re-enforce for you and the supplier exactly what is involved]
• What does your Support Contract/Cost include? [e.g. Does it include: unlimited phone calls to their help-line? All new versions/upgrades?]
• Do you offer a guaranteed response time when I ring up for support?
• How do you record/manage bug reports / Do you have a structured process for when things go wrong?
• How do you provide fixes?
• How often do you release new versions/upgrades, and how are they distributed?
• How do you manage Quality Assurance (QA)? What are your internal testing processes?
• Do you provide remote support? Is this charged for?
• Do you have a user group?
• Can I speak to/visit some reference sites?
• And more general questions about the company such as its size, age, goals etc.
Some specific questions you could ask are:
• Can I speak to one of your clients who used to be unhappy but who you managed to 'turn around' and make them happy? [When I was a salesman years ago, this was one of the most insightful questions I was ever asked; any supplier can give you at least some references who are happy with them, and no-one is going to give you references who hate them! So something like this sort of question is fair to the supplier, lets the supplier show you what they are made of but still gives you good client feedback]
• What could you improve in your software? (What are your weaknesses?)
• Who do you consider are your major competitors?
• What is the main thing that sets you apart from your competitors?
• Can we meet other people in your company? Can we visit your offices?
• What are your future plans?
• How do you keep up-to-date with new technology?
It can be a difficult skill, but it is often what a salesperson doesn't say which is just as revealing as what they do say (e.g. especially if you ask what the weaknesses are in their product!). Listen out for when they avoid answering any particular question, ask it again if you feel it is valid to do so, but either way, note what happened and you can consider later if there is anything you thus need to be concerned about.
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