Microsoft Plans Ground-Up AI Rebuild of Outlook Under New Leadership

Outlook’s AI Transformation

Microsoft is shaking up its Outlook team with ambitious plans to completely rebuild the venerable email client for the artificial intelligence era, according to recent reports. Rather than simply adding AI features to existing software, sources indicate the company wants to reimagine Outlook from the ground up as what one executive called a “body double” for users.

The reorganization places Gaurav Sareen, corporate vice president of global experiences and platform at Microsoft, in direct leadership of the Outlook team. Internal memos obtained by technology publications reveal Sareen is taking over from Lynn Ayres, who is reportedly taking a sabbatical from the company. This leadership change signals Microsoft’s serious commitment to transforming one of its most essential productivity tools.

From Tool to Partner

What exactly does an “AI-native” Outlook look like? According to the internal vision described in reports, Microsoft envisions an email client that reads your messages, drafts replies, and manages your schedule automatically. “Think of Outlook as your body double, there for you, so work feels less overwhelming and more doable because you are not facing it alone,” Sareen wrote in the memo seen by sources.

This represents a significant shift from Microsoft’s current approach with Microsoft Copilot, which functions more as an add-on to existing Office applications. Building AI directly into Outlook’s foundation could potentially create a much more integrated experience—though it also raises questions about how radically Microsoft will change an interface that millions of business users rely on daily.

The company apparently recognizes this won’t be a simple task. Sareen’s memo reportedly calls on Outlook employees to find “courage” to “let go of old ways of working” and embrace faster development cycles. Sources indicate the team is being pushed toward weekly feature experiments instead of quarterly ones, with prototyping and testing measured in days rather than months.

Building on Shaky Ground

Microsoft’s last major Outlook overhaul—the web-based “One Outlook” initiative—has faced significant challenges in recent years. The company has struggled to match the functionality and reliability of the desktop applications it’s meant to replace, creating skepticism among power users. Now, adding unproven AI features into the mix represents an even bigger gamble.

Industry observers note that executives worldwide depend on their Outlook calendars and email workflows for critical business operations. Any misstep in transforming this essential tool could have serious consequences for Microsoft’s enterprise customers. The company will need to balance innovation with stability as it moves forward.

This Outlook reorganization appears part of broader changes across Microsoft’s productivity division. Ryan Roslansky, who leads LinkedIn, took on expanded responsibilities earlier this year as head of Office in what analysts described as an AI-focused shake-up. Sareen now reports directly to Roslansky, creating a leadership structure focused squarely on Microsoft’s AI ambitions.

The Cultural Shift

Perhaps the most revealing aspect of the reported memos is how deeply Microsoft wants to embed AI into its development culture, not just its products. “AI will not just be in our product, it will define our culture, helping us move at the speed this moment demands,” Sareen reportedly wrote.

This cultural transformation may face internal resistance. Sources familiar with Microsoft’s workforce suggest some employees remain unconvinced by the company’s massive AI investments and the direction they’re taking established products like Outlook. Conviding skeptical team members while pushing aggressive development timelines could prove challenging for leadership.

Meanwhile, Sareen’s memo reportedly draws a distinction between genuine AI-native applications and what he calls “buzzword complaint” products that simply slap AI features onto existing software. “Next year, every product will claim to be AI native,” he wrote, according to sources. “But there will be teams that just slap AI on products… and there will be teams that will have actually rebuilt their product and culture from the ground up.”

As the AI race intensifies across the tech industry, Microsoft appears determined to place its biggest bets on transforming core productivity tools rather than incremental improvements. The success or failure of this Outlook overhaul could signal whether email clients are ready for such fundamental transformation—and whether Microsoft’s AI ambitions can deliver on their considerable promise.