Building Delight - Inside Microsoft Product Management

In our latest Polaris episode, I sat down with Sean Squires to demystify what product managers at Microsoft really do. We explored how a product manager blends technical know-how, business strategy, and deep customer empathy to turn ideas into features that millions use and love. Sean is a Principal Product Manager focusing on SharePoint and Content AI at Microsoft, and his insights offered a behind-the-scenes look at how software gets from inspiration to innovation.

We kicked off by framing the challenge all organizations face today: an explosion of data and content. By 2025, IDC projects the world will have 175 zettabytes of data, and around 80% of it will be unstructured documents and media. (If you put that on paper, the stack of paper would be 1.8 light years high.)

Staggeringly, 90% of that unstructured data might never even be analyzed. With content growing at this cosmic scale, finding what you need can feel impossible. Sean and I discussed how this “content chaos” is driving new approaches, like Intelligent Document Processing (IDP) and AI-powered content management. For example, the global IDP market is booming – from $1.1 billion in 2022 to a projected $5.2 billion by 2027 – because businesses urgently need tools to sift and organize their overflowing content.

Sean offered a clear picture of the product manager’s role in tackling challenges like these. A product manager (PM) at Microsoft is not just a coder – in fact, Sean jokes that he’s “dangerous with some coding” but doesn’t write the production code. Instead, the PM is like a producer in a recording studio, orchestrating all the pieces to create a great final product.

Just as Beatles producer George Martin didn’t play on every track but ensured all the parts came together, a ‘Day in the Life’ of a PM is spread acrtoss design, development, and business teams. Sean described Microsoft’s modern approach as a “strong triad” of PM, design, and development working hand-in-hand. He oversees the product lifecycle from idea to launch, translating customer needs into technical requirements and making sure the solution fits within the broader system.

So what does a typical day look like for a product manager? In Sean’s experience, no two days are the same, but they are always busy! He might start by reviewing a design prototype, then jump to a meeting about technical dependencies, later write or refine a feature specification, and then sync with marketing or documentation teams about an upcoming release. In short, a PM wears many hats. Here are just a few of the things a product manager might do on any given day:

• Coordinate with design and engineering to review UI mockups and development progress.

• Write and refine specifications and requirements for new features or improvements.

• Meet with stakeholders across marketing, support, and leadership to align on product goals and timelines.

• Analyze customer feedback and data to prioritize the product backlog and make decisions.

• Test new features early, gather internal feedback, and iterate on the design.

One mantra that came up is moving from a Minimum Viable Product to a Minimum Lovable Product. Product managers often release an early version of a feature (an MVP) to test the waters. But Sean notes that “one has to very quickly lead to the other”. It’s not enough for a feature to merely function; it should eventually delight users. We discussed how the team approaches building “magic moments” into the product.

A great example was a feature Sean worked on called Autofill in Microsoft SharePoint. Autofill is a recently introduced capability that uses AI to auto-populate metadata for documents. In a SharePoint library, users can add a custom column that automatically generates values based on an AI prompt. For instance, instead of manually tagging hundreds of files with a project name or a summary, you can instruct Autofill to “summarize this document in one sentence” or “extract the invoice total”, and it will fill in that column for every file with AI-generated answers.

Sean recalled testing Autofill: “What you used to have to do manually, all of a sudden our system is reading the document and capturing the answer for you at scale. That’s delightful.” 

Beyond the wow factor of AI features, Sean stressed that user trust and adoption are paramount. We chatted about how introducing advanced AI capability has to be done with an understanding of human psychology and workflows.

There’s an example from sports: in baseball, you could put a chip in the ball and have a computer call balls and strikes more accurately than any human. Technologically, an automated strike zone works – but in fact, over 60% of MLB players surveyed said they are not in favor of “robot umpires” taking over the calls, and many fans also resist removing the human element.

On the other hand, we’re totally fine letting navigation AI like Apple Maps or Google Maps tell us when to turn left. For product people, the lesson is that technology must account for human readiness and comfort. “There are people who aren’t willing to let AI have a central role in how they work,” Sean observed. A great product manager needs to gauge when to keep a human in the loop and when users are ready to trust the AI fully.

Sean emphasized that empathy for the customer’s perspective is crucial for product development, as direct interactions often reveal unexpected use cases and inspire new features or improvements. It also means filtering what customers ask for through the lens of what they actually need. This is where the famous (and possibly apocryphal) Henry Ford quote comes in: “If I had asked people what they wanted, they would have said a faster horse.” In other words, users often frame requests based on the familiar (faster horses) rather than envisioning something new (the automobile.)

I was curious how working with newer cloud and AI technologies has changed Sean’s perspective, given his history with older software stacks. He gave a delightful analogy involving music: Irving Berlin, the famous songwriter, could only play piano in one key (F# major, all black keys), so he had a special piano with a lever that would shift the keys mechanically to other pitches[6]. This let him play any song in a comfortable way, even if it needed to be in a different key for publishing. Sean likened this to working in one familiar tech stack versus venturing into another. When he stays on the “same piano” (like the SharePoint platform he knows well), he can get things done by instinct. But when he steps into a new environment or integrates with a different system, it forces him and the team to think differently and often more creatively.

In the end, this episode of Polaris really highlighted that product management is both an art and a science. On the science side, you have data, metrics, experiments, and iterations. On the art side, you have empathy, vision, and the drive to create delight. Sean embodies that balance.

For more insights, be sure to listen to the full podcast episode with Sean . As always, I welcome your thoughts – feel free to reach out or comment with your take on product management and where you see it heading, especially with the rise of AI. Thank you for reading, and stay tuned for the next Polaris Pathways conversation!

Polaris is available on Apple, Spotify, Amazon, YouTube or wherever you get your favorite podcasts. Thanks.

Credits

Polaris is produced with the help of our friends at Riverside.fm. Our theme song, “Alternative Dream” is provided courtesy of Adobe.  Additional music and sound provided by IndieGuy Records. Graphic design by Josh Brantley.

Show Notes

Quotes

“Customer empathy is the cornerstone of building a good product.” – Sean Squires

“A minimum viable product must quickly become a minimum lovable product.” – Sean Squires

“Whenever we build a feature, we ask: where’s the magical moment for the user?” – Sean Squires

“Some of the best ideas I’ve seen come directly from customers and the community.” – Sean Squires

References

Data and Business

IDC estimates 175 zettabytes of data worldwide by 2025, with ~80% of it unstructured and 90% of unstructured data never analyzed –

Global Intelligent Document Processing market size growing from $1.1B (2022) to $5.2B by 2027 at 37.5%

Major League Baseball – ~63% of surveyed MLB players do not want robot umpires (Automated Ball-Strike system), preferring the human element – https://bleacherreport.com/articles/25204707-mlb-pitcher-says-potential-abs-robot-umpire-rule-change-would-ruin-baseball

Henry Ford’s “faster horse” quote – “If I had asked people what they wanted, they would have said a faster horse.” (Often attributed to Ford to illustrate innovation beyond customer requests; actual origin is apocryphal) – https://quoteinvestigator.com/2011/07/28/ford-faster-horse/

Steven Sinofsky – “Learning by Shipping” – Blog by former Microsoft Windows president Steven Sinofsky, discussing tech, management, and strategies (includes commentary on AI and product development) – https://learningbyshipping.com/

“Unsolicited Feedback” podcast – A weekly product & growth podcast by Reforge, featuring candid discussions between product leaders on recent tech trends and product decisions – https://www.reforge.com/podcast/unsolicited-feedback

Google NotebookLM – An AI-powered research and note-taking tool by Google that can summarize documents and even generate podcast-like audio discussions from your notes (an experimental project formerly known as Project Tailwind) – https://notebooklm.google/

ModuleQ – An “People-Facing AI” startup founded by David Brunner, which integrates with Microsoft Teams to deliver personalized, proactive insights to professionals (example of AI in enterprise workflow) – https://www.moduleq.com/ 

Pop Culture

“The Pitt” – The Pitt (2025) is a new medical drama TV series set in a Pittsburgh trauma hospital’s ER, noted for its realistic portrayal of medical staff and intense single-shift story structure (starring Noah Wyle) – https://en.wikipedia.org/wiki/The_Pitt

“A Day in the Life” – Iconic 1967 song by The Beatles (from Sgt. Pepper’s Lonely Hearts Club Band), known for its elaborate production – https://en.wikipedia.org/wiki/ADayintheLife

Sir George Martin – Renowned record producer for The Beatles, often called “the Fifth Beatle” for shaping their sound – https://en.wikipedia.org/wiki/George_Martin

Irving Berlin’s transposing piano – Songwriter Irving Berlin used a custom piano with a transposing lever so he could play in one key (F#) and the piano would shift the pitch, allowing him to accompany in any key – https://www.straightdope.com/21343780/if-irving-berlin-couldn-t-read-or-write-music-how-did-he-compose

The Ministry of Time (novel) – The Ministry of Time is a 2024 science fiction novel by Kaliane Bradley, exploring time travel and identity. It gained attention as one of Barack Obama’s recommended summer reads in 2024 – https://en.wikipedia.org/wiki/TheMinistryofTime(novel)

Leon (Leon Bridges album) – Leon (released October 2024) is the fourth studio album by R&B/soul artist Leon Bridges. The album blends retro soul with folk and country influences and has received positive reviews for its storytelling and style – https://en.wikipedia.org/wiki/Leon(LeonBridges_album)

The Intrazone podcast – The Intrazone is a Microsoft 365 podcast (hosted by Mark Kashman and oft-co-hosted by Chris McNulty) that ran from 2018–2025, covering SharePoint and Microsoft 365 topics. (It announced a pause after 220+ episodes in mid-2025) – https://directory.libsyn.com/episode/index/id/36825055

Events

TechCon 365 Seattle | June 23-27, 2025 (Seattle Convention Center)

FY26 Forward - Microsoft Partner Success Strategies - July 29, 2025. A fireside chat about Microsoft's plans for its new fiscal year and how partners can align for success.

TechCon 365 Atlanta | August 11-15 at the Georgia World Congress Center.

TechCon 365 Dallas - | November 3-7, 2025 (Dallas, TX). Irving Convention Center

Microsoft Ignite 2025 – Nov 17-21, 2025 (San Francisco, CA). 

ESPC25 (European SharePoint Conference 2025) | Dec 1-4, 2025 (Convention Centre Dublin (CCD) Dublin, Ireland). 

Chapters

00:00 Introduction to Sean Squires and His Role at Microsoft

06:53 The Role of a Product Manager

09:18 A Day in the Life of a Product Manager

12:25 Navigating Product Development Challenges

15:29 The Balance Between MVP and MLP

18:02 Creating Delightful User Experiences

21:07 Customer Needs vs. Innovative Solutions

24:15 The Importance of Customer Feedback

27:11 Working with Familiar vs. New Tech Stacks

30:02 AI's Impact on Product Development

32:34 Staying Inspired in Product Management

38:58 Introduction to Upcoming Events

40:27 Reflections on Podcasting and Future Directions