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Okay, so you’re about to launch into the brave new world of dynamic web sites. You’re gonna get the fully-loaded sales lead generation tool that integrates with a CMS and has database publishing capabilities. Cool. But before you can sign off on the deal, you have to figure some things out, which means having a chat with the folks in IT. The last time you talked to the guys in IT, you couldn’t really make sense of what they said, but it all sounded really good.

If you’re in this spot, you’ll need to go in there armed with good questions. Here’s a list of starter ones, divided into categories. Compatibility questions can give you a lot of information about what IT supports (or can support) right in house. Responsibility questions help IT formulate who is responsible for what systems–a very important thing to IT. Integration questions help you and IT discuss how to take the new system you are buying and place it in and among other existing systems. Scheduled maintenance and backups questions provide you with an opportunity to find out how robust your IT department’s non-emergency capabilities are.

Compatibility
1. What kinds of servers are we running?
2. What OS (usually Linux/Unix or Windows) and at what versions?
3. What databases are we running (mysql, postgresql, sql server, oracle, db2) and what versions?
4. What scripting languages do we support (php, asp, jsp, .net, python, perl, ruby) and what versions?

Responsibility
1. Do we need a service-level agreement? (SLAs are like contracts that guarantee certain percentage of uptime per month, or a certain response time to incidents, etc.)
2. Can IT support this project in-house, or if they can’t, can we outsource to the vendor?
3. What contact information do you need from the vendor if we do outsource it?
4. Does IT prefer or require a testing period or pilot program before full implementation?

Integration
1. What information do you need to have from the vendor about integration issues?
2. What information do you need to give to the vendor to make integration succeed?
3. Is there any offline or online documentation we can share with the vendor?

Scheduled Maintenance and Backups
1. What is the maintenance schedule for software, hardware, or OS in question?
2. What is the upgrade schedule?
3. What is the security patch schedule?
4. How often is the data backed up or mirrored?
5. Can we outsource backup or maintenance/upgrades of the application to the vendor, or does it need to be handled as part of a larger IT program?

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