The 'Do Less' Philosophy
At the heart of Evan Williams's management philosophy is a principle that seems counterintuitive in the hyper-growth world of tech: do fewer things. He has consistently advised founders to resist the temptation of chasing every opportunity and instead
obsess over a single, important problem. This isn't about laziness; it's about focus. Williams believes that deep, valuable insights only come from concentrating on one thing at a time. He learned this lesson the hard way. His first company, Pyra Labs, nearly failed while trying to juggle multiple projects, but was saved when he was forced to focus solely on a side project called Blogger. Similarly, his podcasting company Odeo was spread too thin, a mistake that was corrected when its own side project, Twitter, became the central focus. This methodical, almost minimalist, approach prioritizes solving a problem correctly over solving it quickly.
A Search for Thoughtful Systems
Unlike the famous Silicon Valley mantra of "move fast and break things," Williams's approach could be described as "move slow and build something meaningful." He views company and product building as a creative process, more akin to painting or writing a book than executing a rigid business plan. This manifests in products designed to be intentional and clean. When he launched Medium in 2012, it was presented as a deliberate antidote to the fleeting, 140-character nature of Twitter. The platform was designed with minimal distractions to help writers focus on their words and find an audience based on the quality of their ideas, not their existing popularity. Williams has often expressed regret over the internet's tendency to reward extremes, stating that the system is "broken." His ventures post-Twitter are attempts to fix that, creating platforms that encourage deeper engagement and more thoughtful content.
The Frustration of Indecision
While a deliberate pace can lead to thoughtful products, for employees and investors, it can feel like paralyzing indecision. This is the core of the criticism against Williams. During his time as CEO of Twitter, and later at Medium, his contemplative style was a source of friction. Some former colleagues have described him as difficult to work with, noting his tendency to take a long time to make final product decisions. This methodical nature has been labeled as a weakness in a fast-moving industry where competitors are quick to seize opportunities. At Medium, this led to several major pivots in business strategy, including abrupt shifts away from an ad-based model that resulted in significant layoffs and left publishing partners in the lurch. For those accustomed to the tech world's sense of urgency, Williams's philosophical quest for the "right" model can seem dysfunctional and out of touch with commercial realities.
Inventor, Not a Manager?
The split in opinion over Williams's leadership often comes down to a fundamental question of roles. Many, including Williams himself, have acknowledged that his strengths lie more in invention and product strategy than in day-to-day management. He stepped down as CEO of Twitter in 2010 to focus entirely on product. His passion isn't for running a large organization, but for identifying a deeply felt human desire and using technology to serve it more conveniently. This focus on the user experience is paramount for him. However, this inventor's mindset has sometimes clashed with the operational demands of being a chief executive. Early in his career at Pyra Labs, he faced criticism for prioritizing business needs over personnel during a financial crunch. This recurring tension suggests that while Williams is a master at conceiving world-changing platforms, he may be less suited to the specific temperament required to run them at scale—a distinction that defines his complex legacy.
