I have been in IT industry for only 9 years, started as System Engineer, Software Engineer and now working as an IT Support for over a year. When I joined this organization (non-profit) I was happy because my main target was met; using Server 2003 and Windows XP was all I needed as IT Support. We were only two in IT department, my and my IT Manager. IT Manager left the company and our Executive Director permanently hired a person while I was in vacation who will be my assistant. I got a big surprise when I came back from vacation, new server installed which is Linux (Ubuntu) and all staff convinced to use Thunderbird against Outlook. My main issue addressed to the big boss (who has no ideas about what’s going on as far as information technology is concerned) was that, why we have to go through this way and actually hired a Linux experienced person (totally non Windows) while most of the software used by the organization are Windows based? Anyway, the answer was that this geek knows a lot especially open source (freeware) stuffs. Since then everything is unstable, staff keep complaining about all try and error applications used. We are only 20 staff and now we have 4 servers because some software need Windows. This costs more than what big boss expected. I believe I have learnt on making decision without gathering requirements and risks, just because software is free might cost you a lot.