Classic Outlook vs. New Outlook: What the Switch Means for Your Team

You probably open Outlook every day without giving it much thought, until one morning something looks different and you are prompted to switch to the new Outlook for Windows. Suddenly, there are new buttons, a new layout, and a new way of working to adjust to.

If you have been working with Microsoft tools for a while, you know this kind of change is inevitable. Many of us remember when the ribbon was first introduced in Outlook and how unfamiliar it felt at the time, even though it eventually became second nature.

In this article, we’ll walk through the key differences between classic and new Outlook and, if you manage a team, what you can do to support them through the transition with as little disruption as possible. We’ll discuss:

• Introducing the New Microsoft Outlook
• The Differences Between Classic and New Outlook
• How to Start Using New Outlook
• Helping Your Team Navigate the New Outlook Experience
• Switch to the New Outlook, the Great Canadian Way

Introducing the New Microsoft Outlook

While Microsoft has been hinting at it for some time, the direction is now clear: the new Outlook is here to stay. Your team may not have been prompted to switch yet, but the transition is coming.

At the time of writing, Microsoft is targeting Enterprise users for a phased automatic switch beginning in April 2026. You’ll still have an initial option to return to classic Outlook. Over time, the new Outlook is expected to become the default experience for Microsoft 365 subscribers, even as classic Outlook remains supported through at least 2029.

The new Outlook is Microsoft’s modern replacement for classic Outlook. It is designed to bring desktop Outlook closer to the web experience, with a cleaner interface, tighter integration across Microsoft 365, and ongoing feature updates.

While classic Outlook is still supported for now, Microsoft is focused on the new version. Over time, new features and capabilities will be available only in the new Outlook experience.

The key takeaway: the transition is not optional in the long term. Planning ahead helps you stay in control of the experience rather than reacting to it.

The Differences Between Classic and New Outlook

Here are just some of the differences between new Outlook and classic Outlook.

For most people, the new Outlook will feel like an improvement once they are more familiar with it. That said, there will be a learning curve because things are no longer where people expect them to be. Buttons might be in a different spot, or menus may open differently. It will just take time to get used to it.

There are a few things that may be unpopular with your team. For example, if your team has been relying on public folders, PST files, or certain older add-ins for years, those workflows may need to change.

How to Start Using New Outlook

Getting started is pretty straightforward.

In classic Outlook, many users will see a “Try the new Outlook” toggle in the top right corner of the app. Turning it on downloads the new Outlook and walks the user through setup.

New devices running Windows 11 version 23H2 or later often come with the new Outlook pre-installed. You can also download it directly from the Microsoft Store if your system supports it.

Your contacts, mail, and calendar carry over automatically.

How Do I Switch Back Between the Old Outlook and New Outlook?

What if you want to switch back to classic Outlook? For example, what if you want to become familiar with the new version but you're in a rush and need to access the classic version you're used to?

In most cases, you can toggle back by turning off the new Outlook toggle or selecting the option from the Help menu in the new app. Classic Outlook will reopen, and work can continue as before.

Helping Your Team Navigate the New Outlook Experience

Any sort of change can be disruptive. If you're a manager or leader, this is where you'll really make a difference.

As a leader, it helps to manage your expectations. This is not just a technical update. It's going to shift how your team works, so you can expect and plan for a temporary dip in productivity.

First, clear communication goes a long way. A simple heads-up about what is changing and how it affects their workflow can prevent a lot of frustration. You can even send them this article so they can understand the differences between the two versions.

Being able to toggle back and forth lets people play around with the new Outlook. Some team members will jump in and adapt quickly, while others will need more time. Encouraging experimentation and allowing a transition period helps manage issues early and builds confidence.

If your team needs to change how they work because of the new Outlook's limitations, it helps to brainstorm workarounds to address them. For example, if your team relies on features such as public folders and PST files, they may need to migrate those emails to a SharePoint site.

More than anything else, training can make a real difference. We created Mastering the New Outlook specifically for teams moving to the new version of Outlook. It gives them a guided walkthrough of the new interface, highlights what's different, and helps them get up to speed quickly.

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Switch to the New Outlook, the Great Canadian Way

At Great Canadian Training, we know that tool changes are rarely just about the tool. They are about the people using it every day.

When any software changes, it shows up in small but frustrating ways. In Outlook, emails may feel harder to find or file. That is why we focus on helping teams get comfortable quickly, not just on technical setup.

Our Mastering the New Outlook course is designed for this transition. It gives your team a clear walkthrough of what has changed, what works differently, and how to use the new features to save time. Instead of learning by trial and error, your team gets guided, practical instructions that connect directly to how they work.

Whether you bring us in for a custom session or enroll your team in one of our public live, instructor-led classes, you can expect fewer frustrations and faster adoption across your team.

If the new Outlook is on your horizon, now is a good time to set your team up for success rather than waiting for the questions to pile up. Reach out to our team to schedule training that makes the transition smoother for everyone.