Is it Time to Update SharePoint? 7 Questions to See if You’re Ready

When it comes to SharePoint, I don’t have a dog in the Classic versus Modern fight. Both have their place, and there’s no one-size-fits-all answer. What I have seen, though, is a big gap in guidance for site owners about when and how to make the decision to modernize (if they have a choice). ?

How to quickly tell if you're using "Classic" or "SharePoint"? Here's a visual:

Deciding whether to modernize your SharePoint site can feel overwhelming, especially when juggling organizational priorities and team needs.?

So how do you know if the timing (and effort) is right? Before jumping in, let’s explore seven essential questions—complete with “symptoms” to watch for and examples of teams who should (or shouldn’t) make the leap.?

??Bonus! ??Leverage the “Should We Migrate?” Decision Tree at the Bottom of This Article at your next team meeting.?

1. Is It An Option? ???

Before planning, confirm your IT environment can support Modern SharePoint and tools like Copilot. If your SharePoint is hosted on your organization’s servers (on-premise) or in a hybrid setup, you might need extra support from IT to enable Modern features like AI. Also consider that while it may be POSSIBLE, it is not feasible due to lack of resources, higher priorities, or budget constraints. ?

Spot the Symptoms:?

• If your IT department hasn’t announced plans to upgrade or has restricted access to Modern features for security reasons, it’s a sign you may need their support to move forward.?

• You can’t request Modern sites or see Modern web parts.?

Stay or Go?

Example of a Team That Should Modernize:?

A marketing team that opts-in to creating a modern site themselves and migrating their old content, working with IT a few times for set up and removal of their old site. ?

Example of a Team That Shouldn’t Modernize (Yet):?

A highly-regulated organization with an on-prem environment cannot access Modern or Copilot until IT makes broader infrastructure changes.?

2. Does Your Current Site Feel Outdated? ????

Classic SharePoint sites may not meet the design and usability standards your employees expect in today’s digital workplace.?Modern pages, with their mobile-friendly layouts and intuitive navigation, can offer a digital experience that feels more familiar to how you, your team, and your users work online.??

Spot the Symptoms:?

• Your site isn’t mobile-friendly, or menus are hard to navigate.?

• Users complain about how difficult it is to find or access information.?

• Visual elements feel dated and aren’t using the latest UI/UX standards ?

Stay or Go??

Example of a Team That Should Modernize:?

A marketing department relying on a clunky Classic intranet struggles with mobile usability for employees in the field. With a dispersed workforce needing quick access to resources on the go, it’s time to upgrade to a Modern site.?

Example of a Team That Shouldn’t Modernize (Yet):?

An operations team with a customized Classic site that works well for their specific processes can wait—especially if they don’t need AI tools immediately and the teams people and processes rarely change.??

3. Are You Missing Key Features? ???

Modern SharePoint integrates seamlessly with Microsoft 365 apps, offers a faster and more accurate search experience, and supports better team collaboration.?Modern SharePoint unlocks new tools that help teams work more efficiently, such as AI assistants like Copilot or automation tools like Power Automate.?If your organization plans to explore AI tools in the future, modernizing your content is an important step—but only when you’re ready to make that leap.?

Spot the Symptoms:?

• You can’t use new tools like Power Automate, Copilot, or Teams integrations.?

• Your workflows feel manual, repetitive, and disconnected from other apps.?

• Search results are incomplete or inaccurate.?

Stay or Go??

Example of a Team That Should Modernize:?

A lean program management team wants to leverage Copilot to generate draft content quickly from their existing library, but Classic SharePoint doesn’t support it. Upgrading to Modern unlocks the ability to use these tools and boosts productivity on small teams.?

Example of a Team That Shouldn’t Modernize (Yet):?

A legal team managing static content doesn’t require or allow dynamic features or AI integrations.?

4. Is Maintenance Becoming a Nightmare? ?????

Classic sites often rely on complex customizations that can make updates or fixes difficult, especially when the person who set them up is no longer available. Modern SharePoint simplifies many maintenance challenges, so team members who aren’t technical experts can manage updates and content more easily.?

Spot the Symptoms:?

• IT spends considerable time patching or troubleshooting custom code.?

• Regular updates break workflows or custom-built features.?

• Site updates depend on a few people with highly specific technical knowledge.?

Stay or Go??

Example of a Team That Should Modernize:?

An HR team uses a heavily customized Classic site for onboarding. The constant need for IT support is draining resources, making a Modern upgrade a practical choice.?

Example of a Team That Shouldn’t Modernize (Yet):?

A nonprofit organization with a straightforward Classic SharePoint site (no custom code) doesn’t face these challenges and can stick with their current setup.??

5. Do Your Users Actually Use Your Site? ???

If your team avoids your SharePoint site or finds it frustrating to use, it’s a sign that an upgrade could make their workday easier. Modern SharePoint’s intuitive design and collaborative features can encourage adoption, making your digital workspace an active hub.?

Spot the Symptoms:?

• Low engagement or site visits in analytics.?

• Employees bypass the site in favor of email or other tools.?

• Users have created their own sites, teams, or spaces.?

Stay or Go??

Example of a Team That Should Modernize:?

A sales team’s intranet sees low engagement because Classic SharePoint buries key resources. Sales team members have created ad-hoc content that isn’t aligned to the bigger strategy and direction. A move to Modern could improve content discovery and drive adoption.?

Example of a Team That Shouldn’t Modernize (Yet):?

A finance team uses their Classic site consistently for monthly reporting. If adoption is already high, there’s no immediate need for change.?

6. Are You Thinking About the Future? ???

Microsoft’s investment in Modern SharePoint includes advanced AI tools like Copilot, designed to help organizations stay ahead of the curve. If your long-term strategy is to continue to leverage Microsoft, then preparing to migrate should be seriously considered. ?

Spot the Symptoms:?

• IT announces a move to Modern.?

• The Business has invested in AI experiments, but lack of accessible, well-structured data causes them to fall short of expectations. ?

Stay or Go??

Example of a Team That May Modernize:?

A startup scaling rapidly wants to quickly build out new sites and pages with a consistent look and feel as new departments emerge, then later leverage Copilot to create self-service chatbots for employee onboarding. ?

Example of a Team That May Not Modernize (Yet):?

A local government agency with no growth plans or budget for AI tools can prioritize other initiatives while preparing for future upgrades.?

7. Is This Content Still Relevant? ???

Sidebar: Okay, this one is a bit of a cheat since it should be considered in both. Still, I’m going to say it because it is such an impediment to getting the most out of Modern. ?

Modernizing isn’t just about the site—it’s also about the content. Hoarding outdated files makes search worse and frustrates users. Also consider that AI tools like Copilot rely on well-organized, up-to-date content to provide meaningful insights.?Consider using the transition as an opportunity to organize and declutter. ?

Spot the Symptoms:?

• Your site is cluttered with outdated files with owners that no longer work at your company.?

• Search results are bloated with irrelevant documents.?

• Teams are storing old files “just in case” but rarely use them, causing space issues and additional storage costs. ?

Stay or Go??

Example of a Team That Should Modernize:?

An IT support team overwhelmed by outdated troubleshooting guides uses Modernization as an opportunity to curate content and create more self-service tools for the organization.?

Example of a Team That Shouldn’t Modernize (Yet):?

A research team with extensive archives critical for compliance needs a plan to determine what can and can’t be stored in hard drives offline, working with Legal and Compliance to figure out what needs to be readily available for audits. While this team may WANT to move, it will take longer and require more oversight. ?

Final Thoughts?

The goal here isn’t to push you toward Modern or keep you stuck in Classic. It’s to empower you. You deserve agency over your digital future, armed with the tools and insights to make informed choices that align with your team’s needs and goals. ?

Feeling overwhelmed? Here’s how to move forward:?

1. DIY? Check out Microsoft’s documentation to explore Modern features and Copilot integration. SharePoint Maven is another great resource, as well as many content creators on this platform. ?

1. Need help? Let’s talk! I’ve guided businesses through SharePoint modernization and AI adoption, and I’d love to help you too.?

Let’s connect and explore the possibilities together! ????

Bonus!

Modernizing your SharePoint site positions your organization for future innovations, but only when the timing aligns with your team’s goals.?Use the below tool to think through timing.