​If you're working with a website or system that feels like it was built in the early 2000s, you're not alone.

Many businesses are still using legacy systems that are outdated, difficult to update, and not very user-friendly. Eventually, you reach a point where patching it up just won't cut it anymore—and that's usually when folks start looking into newer, more flexible platforms like Kentico.

But here's where things get tricky.

The idea of moving from a legacy system to something new sounds great… until you think about downtime, costs, data loss, or your team having to learn a new platform. If any of that sounds familiar, don't worry—you're asking the right questions.

Let's walk through how you can migrate your legacy system to Kentico in a way that avoids big disruptions, keeps your team sane, and actually improves your return on investment (ROI).

What Is a Legacy System?

Before diving in, let's get on the same page.

A legacy system is usually a piece of old software or an outdated platform that your business has relied on for years. It still works, but just barely. It's probably missing new features, takes too long to update, or feels clunky for your users. Most importantly, it holds your team back from moving forward.

These systems often:

• Rely on outdated code or frameworks
  
  
• Don't play well with modern tools
  
  
• Have slow performance
  
  
• Lack mobile responsiveness
  
  
• Make content updates a nightmare
  
  

So yeah, if you're spending more time maintaining your website than growing your business, that's a red flag.

Why Kentico?

So, why Kentico? Why not WordPress, Drupal, or something else?

Well, Kentico is a hybrid CMS. That means it gives you the best of both traditional CMS (where content and design are tightly connected) and headless CMS (where content can live separately and get pushed out to any platform—web, mobile, apps, etc.).

Here's why I like it:

• It's built on .NET, which is fast and secure
  
  
• It's customizable but not overly complex
  
  
• Marketers and developers can both use it without butting heads
  
  
• It supports personalization, eCommerce, and automation all in one place
  
  

And if you partner with a Kentico development company, they can help tailor everything to your specific needs—without reinventing the wheel.

Challenges You Might Face Before Migration

Let's be real—migrating isn't just plug-and-play. If it were that easy, we'd all be doing it overnight.

Here are some common concerns I hear (and have seen firsthand):

• What if something breaks during migration?
  
  
• Will we lose any of our content?
  
  
• Is this going to interrupt our live website?
  
  
• Will it take forever?
  
  
• Do we need to retrain the entire staff?
  
  

These are valid concerns. But here's the good news: with the right prep and support, you can handle all of these without too much drama.

Step 1: Take Stock of What You've Got

Start with a full system audit.

This step is easy to skip—but don't. You want to know exactly what your current system is doing before moving to something new.

Make a checklist of:

• Page templates and layouts
  
  
• Content types and categories
  
  
• Media files (images, videos, PDFs, etc.)
  
  
• User permissions and roles
  
  
• Any integrations (CRMs, payment gateways, APIs)
  
  
• Current performance issues
  
  

Treat it like packing for a move. Don't just throw everything into boxes. Figure out what's worth keeping, what can be cleaned up, and what's better off left behind.

Step 2: Set Clear Goals

Ask yourself (and your team): Why are we migrating?

Here are a few reasons people usually give:

• We want faster page load times
  
  
• We need to connect with our CRM and marketing tools
  
  
• Our editors hate using the current system
  
  
• It doesn't work on mobile properly
  
  
• We're losing traffic because of technical SEO issues
  
  

Write your goals down and prioritize them. You'll thank yourself later.

Step 3: Choose the Right Version and Environment

Kentico has a few versions. If you're migrating, go with the latest—Kentico Xperience. It's cleaner, more modern, and designed to last.

Also, don't start on your live site. Set up a staging environment. It's basically a test version of your site where developers can work without affecting the live version.

I always recommend doing this in parallel. Let your current site stay up while the new one gets built in the background.

Step 4: Migrate in Phases, Not All at Once

Here's where a lot of folks trip up—they try to move everything at once. Instead, break it down into chunks:

1. Start with static pages (like About Us, Contact, etc.)
   
   
2. Move to core service/product pages
   
   
3. Shift blog or news sections
   
   
4. Finally, handle integrations and backend systems
   
   

Bonus Tip: During this phase, run both systems side by side. That way, if something doesn't work, your old site is still live and operational.

Step 5: Minimize Downtime Like a Pro

Downtime doesn't have to mean hours of users staring at error messages.

Here's what works:

• Schedule the final switch during off-hours, like late night or early weekend mornings
  
  
• Communicate clearly with your internal team—let them know about the content freeze window
  
  
• Test your redirects so users don't end up on broken links
  
  
• Have a rollback plan just in case you need to switch back temporarily
  
  

Keep everyone in the loop—from developers to marketers to customer support. If everyone knows the plan, the risk of surprises drops.

Step 6: Rebuild Your Integrations

Most legacy systems are tied into other tools—like CRMs, email systems, ERPs, and analytics.

Now's a great time to rethink how those integrations work.

Ask:

• Do we still need this tool?
  
  
• Is there a better way to connect it using Kentico's built-in tools or APIs?
  
  
• Are there any bottlenecks we can fix now?
  
  

It might take a bit of development work, but your post-migration setup will run way smoother.

Step 7: Measure Success

After the migration is done, keep a close eye on:

• Page load speeds (they should improve)
  
  
• Bounce rates (they should go down)
  
  
• Conversions or leads (hopefully go up)
  
  
• Content publishing time (should drop)
  
  
• Feedback from editors and site users
  
  

Also, many businesses report lower IT costs after moving off legacy systems. That alone can help cover your migration costs over time.

Final Thought

I've worked with clients who waited way too long to leave their legacy systems behind. It's like using a flip phone when everyone else has smartphones.

Yes, there's work involved. Yes, it costs time and money. But sticking with outdated tech usually costs more in the long run. More delays. More bugs. More unhappy users.

So if you're already looking into Kentico, chances are you're ready. Just don't rush it. Plan it out, find the right partners, and take it step by step.

The result? A website that works the way it should—and a team that doesn't dread using it.