Some individuals appear almost instinctively adept at managing others, naturally understanding how to motivate, coordinate, and guide their teams toward shared goals. Yet for many, effective management is not an innate talent but a learned discipline that requires time, deliberate effort, and often a series of humbling experiences. Such was the case for Dylan Field, who, before later cofounding the design software company Figma, served as an intern at highly regarded technology firms such as Flipboard and LinkedIn. During those early years, he was exposed to organizational processes but had never actually overseen a team or managed people directly. Fast-forward to the present, and Field now leads a thriving enterprise that employs more than 1,600 individuals—a dramatic transition from novice intern to chief executive of an influential global organization.

Reflecting on this evolution in an interview on the podcast “First Time Founders,” Field candidly explained that his first experiences as a manager were not marked by excellence or ease. In fact, he admitted that his early attempts at management were fraught with mistakes and misjudgments, forcing him to learn through trial, error, and self-reflection. He drew a distinction that many professionals overlook: the difference between leadership and management. According to Field, while leadership is often about inspiring people and articulating a vision that others want to follow, management entails executing structure, accountability, and logistics to bring that vision to life. As he succinctly noted, one can easily be a strong leader but a weak manager—or the reverse.

Field described how he initially entered Figma assuming his confidence as a leader would naturally equip him for management. However, he soon discovered that the latter demanded a completely distinct and highly specialized skillset. Among the core capabilities he had to develop were the ability to understand the collective and individual progress of his teams, to cultivate meaningful relationships built on trust, and to conduct effective one-on-one meetings that provided guidance and feedback. He also recognized the necessity of maintaining consistent accountability, ensuring that goals were met, and establishing a reliable cadence of communication and evaluation. When podcast host Ed Elson pressed him on whether he had indeed struggled across all these domains, Field did not hesitate to confirm it. With striking honesty, he replied that at the outset he was “bad at all of it,” underscoring how challenging the shift from creative founder to capable manager can be.

Exacerbating this challenge was the external pressure that Figma faced from its venture capital backers, who were eager to see a market-ready product. Founded in 2012, the company spent several years in development: a beta product reached customers only in 2015, with general availability the following year. It was not until 2017 that Figma began offering a paid subscription plan. Field later warned aspiring entrepreneurs not to interpret this slow timeline as a model to emulate, quipping that taking five years to launch a company could easily doom it before it truly begins. His pointed message served as a cautionary note about balancing product perfectionism with the pragmatic need for timely execution.

A pivotal turning point in Field’s managerial growth occurred when he hired Sho Kuwamoto, who joined Figma as its first dedicated manager and director of engineering. Field credits Kuwamoto with providing invaluable lessons in people management, organizational structure, and the rhythm of effective leadership. Through observing and collaborating with him, Field learned many components of management that can seldom be acquired through theory alone.

Field’s experience represents a broader pattern observed among startup founders who evolve into CEOs. Many innovators begin as creators or visionaries but must subsequently master the complexities of managing expanding teams and scaling company culture. For instance, Dustin Moskovitz, cofounder of both Facebook and Asana, similarly reflected on the taxing nature of management. Leading Asana as CEO for over a decade, Moskovitz described the role as mentally and emotionally exhausting, admitting that his earlier aspiration had been to remain more of an independent engineer rather than shoulder the full responsibilities of organizational leadership.

Similarly, Luis von Ahn, the CEO and cofounder of Duolingo, has offered his own lessons from experience. He once advised that founders should practice a strong degree of micromanagement until their teams reach around thirty employees—enough to maintain quality and cohesion at the formative stage—but confessed that he personally extended that approach too long, continuing hands-on control until his company had grown to fifty employees. Over time, he recognized that his role needed to shift from detailed oversight to embodying the company’s culture, serving as a public representative or mascot, and guiding major philosophical decisions rather than tactical ones.

Despite those early struggles, Field’s reflections on the podcast carried an encouraging and hopeful tone. He emphasized that while management may initially feel foreign or overwhelming to first-time leaders, it is ultimately a learnable competency. With dedication and practice, the knowledge accrued becomes almost instinctual—akin to developing muscle memory. His story stands as a testament to the idea that while some individuals may appear to possess effortless managerial talent, nearly anyone with persistence, humility, and curiosity can refine the art of management and grow into a confident, effective leader.

Sourse: https://www.businessinsider.com/figma-ceo-says-he-was-bad-manager-turned-around-2025-12