Website Maintenance > Redesign Meltdowns

How to Keep Your Nonprofit Site Stress-Free, Budget-Smart, and Mission-Aligned

On June 17, TechSoup Connect Canada teamed up with Dennis Powers and Danielle Thornton of Cheeky Monkey Media for a lively and practical session on avoiding the dreaded website redesign rabbit hole.

If you’ve ever broken into a cold sweat after updating a plugin—or needed therapy after a redesign—you weren’t alone! This session brought a ton of actionable advice and nonprofit-friendly wisdom to the (virtual) table.

🎥 Watch the replay:
 https://youtu.be/wiacwTDNAmU

📊 Download the slides:
 https://drive.google.com/file/d/1IRKE-6JIvtHW8HX4ICXckXgEauJuED_0/view

Top Takeaways: Redesign? Maybe. Smart Maintenance? Absolutely.

Here are the key lessons we heard loud and clear:

  • Redesigns aren’t evil—but they should be rare.
     A full redesign can be necessary when your site is fundamentally broken—like inaccessible, unmanageable, or misaligned with your brand. But for many nonprofits, those big changes can be avoided with smaller, smarter moves. Save the big investment for moments when the return is truly worth it.
  • Iterate, don’t implode.
     Your website doesn’t need to be torn down and rebuilt to improve—it can evolve. Small, strategic updates based on real needs help you avoid massive stress and surprise costs. Iteration also gives your team space to test, learn, and adapt as your goals shift.
  • Maintenance is strategic.
     It’s not just about keeping the lights on—it’s about using your website as a tool for mission impact. Maintenance includes planning, analysis, and enhancements that help you meet goals and connect with your audience. When it’s done right, it becomes a powerful part of your digital strategy.
  • Don’t do it alone..
     With the right support partner, you’re not flying solo—you’ve got experienced help ready to respond when needed. A responsive, knowledgeable team means fewer fires to put out and more space to focus on your mission. Think of them as your digital pit crew, keeping everything running so you don’t have to.
  • Your CMS should serve you.
     WordPress, Webflow, Drupal, Squarespace—there are lots of options, and the best one is the one that meets your needs and capacity. Start with your content goals, your team’s skills, and your budget—not the latest trend. A good platform should make your life easier, not harder.
  • Security isn’t optional.
     Every nonprofit site is a potential target. Tools like WordFence, secure hosting, backups, and regular updates help keep your data—and your users—safe. Don’t wait for a breach to start taking security seriously.
  • Data-driven decisions win.
     Your analytics are full of insights—what’s working, where users drop off, and where small changes can drive big results. Trust the data when deciding what to improve. It’s more effective (and more persuasive) than guessing—or reacting to loud opinions.

Resources and Links from the Chat

Want to Chat with the Presenters?

Dennis and Danielle from Cheeky Monkey Media are happy to help. Whether you’re mid-redesign, overwhelmed with updates, or ready to get strategic:

Join Us Next Time!

Don’t miss our upcoming events—including a July 8 open office hour with David Pisarek to answer your nonprofit website questions:

Check out our upcoming events.