Your IT Guy Is Retiring. Now What?

We see it all the time: a business owner calls us in a panic because their IT person of 20+ years just gave two weeks notice. Or worse—they had a health emergency and can't come back. Suddenly, nobody knows the WiFi password, the server admin credentials, or why that one computer in accounting needs to be restarted every Tuesday.

The Ticking Time Bomb in Your IT Closet

Here's a scenario that plays out more often than you'd think: A small manufacturing company in South Florida has had the same IT guy for 15 years. Let's call him Dave. Dave knows everything—where the cables run, what that blinking light means, why the old printer still works when nothing else from 2008 does.

Dave is also 62 years old and starting to think about his grandkids more than your server room.

When Dave leaves—and he will—what happens to all that knowledge? If you're like most businesses we encounter, the answer is: it walks out the door with him.

The Documentation Problem Nobody Wants to Admit

We recently did an IT assessment for a healthcare practice that had been running smoothly for years. Their longtime IT consultant had everything "under control." When we asked for their documentation, we got a USB drive with a text file containing three passwords—two of which were wrong.

This isn't unusual. In fact, it's the norm. Most small business IT setups exist entirely in one person's head, and that person usually doesn't realize how much institutional knowledge they're carrying around.

The things that need to be documented aren't just passwords. They include:

• Network diagrams showing how everything connects
• Vendor contacts and account numbers
• License keys and renewal dates
• Backup procedures and schedules
• That weird workaround for the accounting software that crashes every month
• Why certain systems are configured the way they are
• Which users have access to what—and why

Signs You're Heading Toward a Crisis

Take a moment to honestly assess your situation. You might be at risk if:

• Only one person knows how your systems work. If that person is unavailable, can anyone else step in?
• Your IT person is approaching retirement age. And you haven't started planning for the transition.
• You couldn't find important passwords if you needed them right now. Be honest—could you access your domain registrar account tonight if you had to?
• Your "documentation" is a collection of sticky notes. Or emails from five years ago. Or nothing at all.
• You've never done a formal knowledge transfer. Because "Dave handles all that."

What a Proper Transition Looks Like

The good news is that this is a solvable problem—if you start before you're in crisis mode. Here's what a healthy IT transition process looks like:

Phase 1: Assessment and Documentation (1-2 Months)

Before your current IT person leaves, you need to capture everything they know. This means sitting down and systematically documenting every system, every process, every vendor relationship, and every weird quirk that makes your setup work.

This is also a good time to identify what's working well and what needs to be updated or replaced. Your retiring IT person might have been holding things together with duct tape and good intentions—better to know that now than after they're gone.

Phase 2: Knowledge Transfer (2-4 Weeks)

Documentation is great, but there's no substitute for hands-on knowledge transfer. Your outgoing IT person should work alongside whoever is taking over—whether that's an internal hire or a managed service provider—to walk through the systems, explain the decisions behind the setup, and reveal all those little tricks that never make it into documentation.

Phase 3: Parallel Operation (1-2 Months)

Ideally, your new IT support should be fully operational while your retiring person is still available as a resource. This overlap period is when you discover all the things everyone forgot to document—and there's always something.

Why Managed IT Services Might Be Your Best Option

Here's something to consider: when your IT person retires, you don't have to replace them with another single person. In fact, that might be exactly the wrong move.

A managed IT service provider brings a team approach to your technology. Instead of relying on one person's knowledge, you get:

• Built-in redundancy. Multiple technicians know your systems, so you're never dependent on one person's availability.
• Standardized documentation. Good MSPs document everything as a matter of policy, not as an afterthought.
• Broader expertise. A team brings diverse skills—security specialists, cloud experts, networking pros—that no single person can match.
• Consistent availability. No more wondering what happens when your IT person takes a vacation or gets sick.

Start Now, Not Later

If your longtime IT person is anywhere near retirement age—or if they're the only one who understands your systems—the time to start planning is now. Not when they give notice. Not when they have a health scare. Now.

The first step is simple: ask yourself what would happen if your IT person wasn't available tomorrow. If the answer makes you uncomfortable, it's time to have a conversation—either with your IT person about documentation, or with us about what a transition plan would look like.

Because Dave will retire eventually. The only question is whether you'll be ready when he does.