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When was the last time you audited the organisation to find out what versions of various software products were deployed? When you conducted that exercise, did you see anything seriously out of date? You'd be surprised at what's still out there. On occasion, I see Windows 98 or NT machines, or Windows XP machines running Office 2000. Ancient software can cause far more issues than some people realise — especially when users are collaborating with other companies, which are unlikely to be running Microsoft Office 98 or StarOffice.
Depending on what is being targeted, if you keep getting hacked, ancient software could be your weak spot. Of course, the breaches could be either hardware or software related, and you may be suffering from poorly configured security hardware, buggy or outdated software, or lax security policies. But while one break-in is understandable, multiple hacks suggest it is time for a major overhaul.
When rival companies overtake you in terms of technology, they can offer customers features and products that are closed to you. Your competition may have taken advantage of the latest technology or perhaps they're exploiting their systems and resources more effectively. Meanwhile, you have stuck with what works for so long, that it no longer works. Losing out to rivals in business should be a signal to step back and examine your technology to find out why you're being left behind.