From the turbulence of Windows Vista to the ambitious leap with Windows 8, Steven Sinofsky’s journey at Microsoft shed light on the realities of leading change within a large organization. Postman’s Jean Yang (Head of Product – Observability) sat down with Sinofsky in a recent episode of Breaking Changes to hear about his experience navigating the complexities of reinventing a mature product. These insights are not only applicable to tech companies but are also relevant to any industry undergoing rapid transformation. Here’s what business executives can take away from this narrative.
Embrace reinvention, even when you’re at the top
One of the standout lessons from Microsoft’s journey is that even market leaders must be willing to reinvent their products to stay relevant. As Sinofsky recalls, Bill Gates foresaw the need to reinvent Windows despite its market dominance, declaring, “We need to reinvent our product.” This approach is critical for staying ahead, especially when a product becomes mature.
Why it matters:
- A 2023 McKinsey report found that the disruption caused by innovation is less risky than maintaining the status quo.
- According to research by MIT Sloan Management Review, companies that continuously innovate and adapt their business models outperform those that rely on traditional methods. Constant iteration enables organizations to stay competitive and respond effectively to market changes.
Advice for leadership: Constantly evaluate your product’s lifecycle. Even when your product is winning, the market is evolving. Proactive reinvention prevents complacency and ensures that your product remains competitive in the long term.
Recognize the dangers of “second-system syndrome”
The Windows Vista project encountered challenges due to “second-system syndrome,” a concept introduced by Fred Brooks in The Mythical Man-Month. In his book of software engineering essays, Brooks claims that following the success of a first system, the second system designed by the same person is the most volatile; it’s likely to be over-engineered and include everything that was trimmed from the first system. In this scenario, teams reinvent features that were already sufficient, resulting in bloated, unfocused projects. For Vista, the push to introduce a new file system, rework graphics, and redefine transactions led to inefficiency and delays.
“We had all of these huge projects… really no other way to describe it than a really giant and consistent case of second-system syndrome. And that became Windows Vista.”
—Steven Sinofsky, Microsoft
Why it matters:
- Harvard Business Review reports that successful innovation requires a willingness to experiment, but with a high degree of discipline to avoid over-engineering and unnecessary complexity.
- According to a 2024 study in Technovation, many innovation projects fail because organizations don’t fully understand the causes of failure or implement effective strategies to learn from them. This reinforces the idea that success in innovation requires not just experimentation but also a strong grasp of failure patterns and how to leverage them for learning and improvement (Freisinger & McCarthy, 2024).
Advice for leadership: When reinventing or upgrading products, avoid the temptation to overhaul elements that are already working well. Focus on improvements that deliver real customer value.
Understand when a product is good enough
Windows 7 was developed with the mindset of creating the “last release of Windows”—a product that met customer needs and didn’t overreach. This focus on delivering a stable, reliable product allowed Microsoft to restore its credibility after Vista’s challenges. The lesson here is that perfection can be the enemy of progress. The experts agree—Jeff Sutherland, one of the co-creators of Scrum, argues that delivering a product that’s “good enough” at regular intervals is far more efficient than waiting to deliver a perfect solution. His book, Scrum: The Art of Doing Twice the Work in Half the Time, details how Scrum’s iterative, incremental approach helps organizations identify when a product meets user needs sufficiently, allowing teams to release it and gather valuable feedback quickly.
Why it matters:
- Research from the Standish Group’s CHAOS Report shows that projects classified as “very complex” have a much higher failure rate (28%) and are rarely successful (15%). In contrast, simpler projects have a much greater chance of success (38% for “very easy” and 35% for “easy” projects).
Advice for leadership: Prioritize delivering a product that fulfills core customer requirements rather than chasing unnecessary perfection. Aim for products that are “good enough” to meet market expectations and leave room for future iterations.
Navigate the tech enthusiast paradox
Tech enthusiasts, who are often early adopters and influencers, can be both an asset and a hindrance. They are invaluable when building momentum for a new product but can resist significant changes later on, as seen with the backlash to the removal of the Start menu in Windows 8. This resistance can be explained by the power user curve, which shows that a small percentage of users—typically the most engaged and vocal ones—are responsible for the majority of product feedback and feature requests. These power users, who often fall into the tech enthusiast category, tend to be highly invested in the product’s existing features and can be the most resistant to changes that disrupt their established workflows.
“The biggest constraint are the tech enthusiasts… they have the most vested interest in basically changing the weirdest parts of it and not changing the parts that need the most changing.”
—Steven Sinofsky, Microsoft
Advice for leadership: Balance the needs of early adopters with the broader market. Engage with tech enthusiasts, but avoid letting them dictate the entire product roadmap, especially when targeting a wider audience.
Team building through shared experiences and clear frameworks
Sinofsky emphasized the importance of team cohesion, highlighting that shipping software together was the most effective team-building exercise. The “storming, forming, norming, performing” framework he referenced, an approach developed in the 1960s by Bruce W. Tuckman, helped his team achieve high performance, even in the face of challenges.
“What makes a team is shipping software together… it wasn’t because of the team building, it was because of shipping. And shipping really is like the thing that builds teams.”
—Steven Sinofsky, Microsoft
Why it matters:
- Research reported by Harvard Business Review shows that teams with strong bonds and shared goals are more productive, creative, and collaborative.
Advice for leadership: To build high-performing teams, focus on creating shared experiences around tangible deliverables. Utilize structured frameworks like “storming, forming, norming, performing” to guide team development stages.
Speed and timing are everything in product development
One of Microsoft’s significant achievements was delivering the Windows 8 operating system, built on an entirely new chipset, user interface, and programming model, within three years—on time. This accomplishment was a testament to efficient project management, team alignment, and a sense of urgency.
Why it matters:
- McKinsey research found that companies that ship software faster can respond more quickly to market demands, customer feedback, and competitive pressures. This faster time-to-market directly contributes to higher revenue growth, with the top quartile of companies studied achieving 60% higher shareholder returns and 20% higher operating margins.
Advice for leadership: Prioritize speed and timing when introducing new products or features. Delays can result in missed opportunities, especially in fast-moving markets.
Accept and learn from failure
Windows 8, despite being a technical marvel, faced challenges in adoption because it didn’t fully align with market expectations. Sinofsky acknowledges this by saying, “What the market wanted from Windows was Windows.” The failure to bridge this expectation gap offers a lesson in listening to customer needs.
Why it matters:
- A 2010 study from the University of Colorado Denver found that organizations learn more from failure than they do from success.
- Additional research from the Rutgers Business Review shows that learning from failures helps companies build organizational knowledge and drive innovation, leading to long-term growth.
Advice for leadership: Not every innovation will succeed, but every failure provides valuable insights. Be willing to pivot based on customer feedback and market realities.
Final thoughts
Steven Sinofsky’s experience underscores that successful product development is a complex interplay of market understanding, disciplined reinvention, and team cohesion. For business leaders, the path to innovation lies in recognizing when to evolve, embracing the constraints of legacy products, and ensuring that your team is equipped to handle the challenges of change.
As you lead your organization into the next wave of advancing technology, remember that reinvention isn’t just about changing products; it’s about reshaping your team, your strategy, and your approach to meet the demands of an ever-changing market. Embrace the challenges, learn from the past, and drive forward with a vision that is both bold and adaptable.
For more of Steven Sinofsky’s insights, check out the full episode, “When Windows Hit the Wall: Reinventing a Dominant Product in a Changing Market.“ Learn more wisdom from industry experts by subscribing to Breaking Changes on Apple, Spotify, and YouTube.