Project Management Lessons from Building Microsoft’s Cortana

Ten years ago, Apple launched Siri, its voice-activated digital assistant for iOS. In turn, that kicked off a race between the tech giants to launch smart A.I. apps capable of responding to all kinds of spoken queries. Microsoft was one of those competitors—and a new breakdown of its efforts makes for fascinating reading.

For the Big Bets newsletter, Alice Netwon Rex spoke to Sandeep Paruchuri, a former product manager at Microsoft, about the development of Cortana, Microsoft’s A.I. assistant. Back in 2011, following the launch of Siri, Paruchuri and other product managers on the Windows Phone team began to brainstorm ideas for the “perfect personal assistant.”

By the next year (following the launch of Windows Phone 8), the team had begun to consolidate their ideas. They created a “poster show” that demonstrated how a digital assistant could impact the life of a hypothetical customer. That convinced management to give them some resources to explore the concept further.

But given the time-crunch around the development of Windows Phone, Paruchuri and team found themselves in the unenviable position of trying to figure out Cortana’s final form even as they built it. “Sandeep and his fellow PMs were now able to pull in other people from across the business to start working on scenarios with them (‘Microsoft was going through a scenario-driven product moment, not a feature-driven moment’), such as people from calendars and audio,” the newsletter added. “Having then created a list of scenarios much longer than what they could possibly build, they found themselves with a prioritization exercise.” 

As the work progressed, and some potential features failed to work, Paruchuri and team began to cut more cool stuff such as proactive transit alerts. However, they were able to improvise at key moments, while also persuading upper management to continue investing resources in the product. “For example, we’d sneak in new features as bug fixes, or we’d hijack the commercialization releases for further features or polish. We did outrageous things, like turning up to release committee dressed in onesies so that they’d laugh and let our feature in,” Paruchuri said.

The saga around Cortana underscores the complexity of tech projects, and how companies everywhere need project managers who can juggle multiple elements on tight deadlines while staying within budget. According to Emsi Burning Glass, which collects and analyzes millions of job postings from across the country, project management topped the list of employers’ most-requested tech skills throughout 2021, ahead of technical skills such as Java, SQL, Python, JavaScript, and more. 

The median project manager salary is $80,280, according to Burning Glass, which rises with skills and experience. On a basic level, anyone aspiring to become a project manager should master project-management methods such as Agile, Scrum, Kanban, and Waterfall. That’s in addition to learning any tech skills needed for your particular area of specialization—for example, mobile app development or hardware. The story of Cortana’s development (which, again, is well worth reading) shows how a mix of technical and “soft skills” is necessary to push a project over the proverbial finish line.