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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be either hardware or software related, and you may be suffering from poorly configured security hardware, buggy or outdated software, or lax security policies.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.
How often do your end users complain of network slowdowns? Can your clients get quick access to your services or sites? If complaints are coming in faster than you can troubleshoot them, it might be time to reassess the backbone. The amount of data being transferred through your pipes isn't the same as it was five or 10 years ago. With so many more web-based tools in play, data usage has gone through the roof. Slow data means slow workers and a slowdown on profit. Share that idea with the board or the CEO and see how quickly they move on upgrading those data pipes.