Can I grow with this software? Will the software you buy today fit your business tomorrow?  Good software is flexible and can be expanded and changed to fit your changing business needs. Whatever software you choose, look at it as a long-term solution. The last thing you want to do is to change technology/software every six months or every year because the software is not meeting your needs.  Before you purchase software you should look at it as a 3 year commitment at least and plan accordingly.

Will this software add value to my recruiting process?  Whatever software you use should enhance and add value to your over recruiting process.  For example, does the software make it easier to process resumes and match candidates to appropriate jobs?  Make sure that you involve employees at all levels when making a decision about the type of software you are going to use to insure that it appropriately meets all of your business needs.

Will this software integrate seamlessly with my existing and future software solutions? Any software solution that you purchase must seamlessly work with your existing and future software in order for your technology to be a help not a hindrance. When assessing software for your company, speak with the software representatives about what programs the software works with and which programs may require additional "bridge" solutions to offer seamlessly technology.

Is this software "user-friendly"?  One of the biggest mistakes of many recruiters is that they purchase software that is a good "solution" on paper but is unusable or difficult to use by ordinary workers.  Whatever software you purchase make sure that is easy to learn and use.  You may even want to purchase "training sessions" for employees to ease them into using the new technology.