More and more, organizations are moving towards using software and proprietary systems to track workflow, projects, and overall progress. Plugging someone new into such a system whereby that individual has never been exposed to working in such a documented, organized fashion could prove disastrous. While many will adapt to and embrace the new technology, an equal number will be hindered by the need to track every step they take or plan to take. You need to probe on style, on process, and on communication techniques. Asking about prior situations where technological solutions replaced more informal practices, specifically probing on how they adapted OR fought such a change, will help you determine your fit with this candidate.