You've just replaced your IT leader, consultant or MSP. Within a couple of days the replacement is in your office painting a bleak picture of what's facing you. Systems are coming apart at the seams, things weren't being monitored, there's no hardware support, no vendor support, no backups, a poor security posture, and even worse, you're running a bunch of custom-written software that is now impossible to support and impossible to fix if it breaks. They have a plan, but the costs are going to be big.
Then it sinks in. Your business is at risk. Not at risk of losing a client or a key employee. You're at risk of losing everything. You aren't protected, you aren't backed up, your hardware is on the verge of collapse, and if it fails, or you get breached, that's it: you're going down. Everything is gone. Many businesses do not survive that, and you had no idea.
It may sound like I'm painting the worst-case scenario. Let me tell you, in nearly 20 years in the MSP business I came across a prospect in some version of this situation at least once a year. Sometimes it was someone who overspent and built such a complex infrastructure that they couldn't afford the expertise to look after it. Sometimes they'd underspent, and everything was open source or custom software running on some ancient version of Linux on recycled hardware, all held together by custom scripts and manual processes. Sometimes it was just outright unprofessional conduct, and they weren't covering all the bases.
So how do you prevent something like this from happening to you? Much like most people audit their books, you should have someone auditing your technology each year. Your IT leader or MSP may not love it, but it's worth your peace of mind to have someone objective tell you whether you're carrying risks you don't know about.