Raylene Yung, a respected figure in engineering leadership from Facebook and Stripe, once described her journey as both gradual and a thrilling, challenging ride. Her initial foray into engineering management at Facebook in 2011, on a small team, was a blend of coding and learning the ropes of recruitment and mentorship. This experience set the stage for a rapid ascent, as her team expanded significantly, and her responsibilities grew from code reviews to strategic company metrics and team building across multiple locations. By 2015, Yung had become the youngest engineering director at a major public company, a remarkable leap from her beginnings as a new graduate at a much smaller startup.
Her move to Stripe presented a new challenge: to prove her leadership capabilities in a different environment. During her four years at Stripe, as the company scaled dramatically, she spearheaded the product management team, established frameworks for career progression and hiring, managed the core Payments business, and launched Stripe’s engineering hub in Singapore.
These diverse experiences at rapidly growing startups provided her with a key insight: personal growth is deeply interconnected with company growth. At Facebook, she focused on absorbing knowledge from experienced leaders joining the expanding company. At Stripe, she became one of those leaders, responsible for guiding and teaching others. This involved learning through practical experience, seeking advice from peers and mentors, and pursuing coaching and training.
This intensive learning culminated in resources like Stripe’s Atlas guide to scaling engineering teams and her own handbook for engineering teams, covering areas from one-on-ones to performance evaluations. After a decade in high-growth startups, Yung took a break to reflect and share her accumulated wisdom, particularly focusing on career growth for engineers. While considering various career trajectories, including paths perhaps tangentially related to fields like medical coding reviews in 2015, Yung emphasizes a broader perspective. She advocates for a focus on comprehensive learning and development rather than solely rapid advancement. In an exclusive interview, she shares counterintuitive career lessons learned through experience, clarifies the intertwined nature of individual contributor (IC) and management tracks, and addresses common obstacles at each career stage, offering guiding questions for self-assessment.
Yung’s insights offer valuable guidance for engineers at all career stages, from those just starting out to seasoned leaders tackling complex challenges. She encourages every engineer to ask the right questions to effectively chart their professional journey.
THREE KEY PRINCIPLES FOR BUILDING A SUCCESSFUL ENGINEERING CAREER:
Throughout her career, Yung has relied on three fundamental principles:
1. Aim to be Highly Valuable, Yet Not Indispensable.
Many professionals aspire to be “critical” to a project’s success. However, Yung argues that this position can be precarious. She recalls an experience at Facebook where she was the sole expert on posting permissions, highlighting the downside of being indispensable.
“I was training for my first marathon and had just completed a 20-mile run when I was paged for a live incident. I ended up in my bathtub, fully clothed and exhausted, surrounded by Gatorade and my laptop, trying to resolve the issue,” she recounts. “It was both exhilarating and frustrating. I felt crucial, but all I wanted was to rest. It was then I decided to prioritize knowledge transfer to my team so they could handle issues independently.”
While the adage “manage yourself out of a job” is common, Yung believes it’s overly simplistic. Her focus is on reducing criticality rather than becoming obsolete.
Being critical implies a decisive role in the success, failure, or existence of something. While this is a position many leaders and engineers find themselves in, it should not be a permanent state.
“Being valuable means you are highly useful and important, but not a single point of failure,” Yung explains. “The best professionals are adept at adding value, maximizing the potential of their colleagues, and anticipating challenges, even in their absence.”
2. Cultivate Emotional Stability for Management Success.
It’s now widely recognized that forcing engineers into management is a misstep. The real challenge lies in engineers deciding if management is a path they genuinely want to pursue. “While management transitions can be rapid, thoughtful consideration and preparation are crucial. Many engineers jump in without adequately exploring management responsibilities beforehand,” Yung advises.
“I started by taking on additional team responsibilities and mentoring new hires at Facebook. I led a significant technical project, which allowed me to balance engineering tasks with leadership duties. By the project’s completion, I was confident in my desire to develop into a capable manager.”
Management is a demanding role. While it presents significant challenges, it is also deeply rewarding, and I have dedicated considerable effort to improving my management skills.
Even with thorough preparation, the emotional demands of management can be unexpected. “This is a frequent topic in my coaching sessions with new managers,” says Yung. “As an IC, you don’t fully grasp the emotional spectrum managers navigate. It’s easy to underestimate the challenges and feel overwhelmed when you realize the reality.”
To illustrate the emotional journey of management, Yung uses a whiteboard chart as a visual metaphor, detailed further in her article on portfolio theory for management:
“As an individual contributor, progress often resembles a steady climb. Projects typically move forward incrementally until completion or a setback. Either way, the next project starts anew,” Yung explains.
However, engineering managers often operate in the “negative zone” of this chart. “As an IC, I was a perfectionist, thinking in absolutes and exhaustively considering all edge cases,” she recalls. “As a manager, I learned that people problems aren’t solved with optimization algorithms. There’s a spectrum of solutions, not a single perfect answer.”
Furthermore, progress and emotional state are no longer directly linked. “As an IC, project success often correlated with visible progress and positive feelings. As a manager, you can invest significant effort over a long period with little short-term progress, and any payoff may be distant and uncertain,” Yung notes.
This can lead to unpredictable emotional lows. “Mood swings become more pronounced. With larger teams, the likelihood of something going wrong at any time increases. The highs and lows become more extreme,” she says. “The first step is recognizing this as normal. The second is developing emotional equilibrium to avoid being easily derailed.”
Experienced managers excel at weathering storms and maintaining emotional stability.
Yung also points out the risk of “split-brain syndrome” in managers. “You may present a composed, steady exterior to your team, while internally experiencing emotional turbulence,” she says. “Don’t isolate yourself. My closest work friends and mentors are those with whom I’ve been most open and vulnerable, and they have been instrumental in my development as a leader.”
3. Prioritize Growth and Learning at Each Stage, Not Just Rapid Advancement.
Despite industry emphasis on career ladders and levels, Yung questions if this is the most effective framework for engineers. “While companies have developed ‘parallel’ ladders for IC and management tracks, and I contributed to this at Stripe, I now see these roles as interconnected steps in a joint progression,” she explains.
Yung visualizes these steps as follows:
“We are fortunate in engineering that management isn’t the only path to advancement. However, many still believe it’s a binary choice, a locked path once chosen. In reality, the skills for technical leadership and management are highly related. I’ve seen numerous individuals transition between these roles, even within the same company,” she says.
“At Stripe and Facebook, I hired ICs who were former managers seeking a break. They all shared the ability to dissect complex problems and deliver on technical projects. This ability was evident regardless of their current ‘ladder’ position. This career flexibility is only possible if you have cultivated both strong team and technical leadership skills.”
Management and IC careers are not strictly parallel; they often intersect. But toggling between them later requires early groundwork. Prematurely pushing for management may leave your technical skills underdeveloped.
Yung observes that many engineers prioritize rapid upward mobility, frequently asking questions like, “How do I become a manager?” or “What’s my next promotion?” or “How can I expand my team?”
“These questions focus on accelerating ladder climbing, which can create a rigid, limiting career path,” she cautions. Instead, Yung advises engineers to engage in deep introspection to understand their motivations and passions before pursuing the next step.
“It’s about asking the right questions, those that center on growth and learning, not just advancement. My most effective team members consistently sought to identify weaknesses, learn from mistakes, and improve,” she says.
My best career advice for young engineers is to focus on learning, not career tracks. This approach ensures continuous improvement, regardless of whether you become an IC, domain expert, engineering manager, or even a PM.
In the following sections, Yung provides tailored advice for each career step, highlighting common pitfalls and suggesting more productive questions for engineers to ask at each stage, drawing from her own career journey.
ADVICE FOR EARLY-CAREER ENGINEERS AND ICS: ESTABLISHING A SOLID FOUNDATION
Many new engineers are characterized by eagerness, drive, and impatience. However, Yung points out that this impatience, if misdirected, can be detrimental.
She identifies three common missteps for early-career engineers:
- Prematurely pivoting from engineering fundamentals to other roles: “Some engineers lose focus on core engineering work too early, aiming for management or roles like product management. Building a strong foundation is crucial, regardless of your ultimate career path,” she emphasizes. “Don’t rush through the fundamentals. Hands-on coding experience is irreplaceable.”
- Moving on from teams or companies too quickly: “As a hiring manager, I’m wary of candidates who claim to have ‘learned everything’ at a company within a year and are ready to move on,” she says. “Often, the most valuable challenges emerge after several years. Overlooking these long-term learning opportunities by prematurely leaving a role is a mistake. The best engineers deeply understand systems and products, applying their experience to new problems.”
- Chasing fleeting trends: “Early engineers often ask me, ‘How can I learn more about [latest technology]?’” Yung notes. “Technology is constantly evolving, and while staying informed is important, prioritizing trendy frameworks over fundamental skills is a poor trade-off. At Facebook and Stripe, interviews are conducted in the candidate’s preferred language, based on the belief that strong engineers can adapt to new technologies. Over-indexing on the ‘new and shiny’ is also unnecessary; what’s old can become new again. For instance, when Android emerged, ‘good Android developers’ were rare. Product teams were initially staffed with infrastructure Java developers, whose experience with parallelism and multithreaded applications proved more relevant to Android than the asynchronous patterns of the web app.”
Frameworks evolve, but core programming principles—edge case thinking, debugging, language adaptability—endure.
Instead, ask these questions:
Instead of focusing on premature role changes, rapid job hopping, or chasing trends, Yung suggests focusing on these guiding questions:
- How can I ensure every code change is excellent? “This may seem granular, but each commit is a building block in software engineering. Building confidence through code reviews accelerates progress and prepares you for larger challenges,” she explains. “Conversely, if each pull request is a struggle and common errors persist, building team credibility is difficult. I often advise new engineers to always self-review code before submission. Catch your own mistakes and learn to avoid them.”
- How can I achieve the skill level of [a specific teammate] in [a particular area]? “[Mentors are diverse and always accessible—identify their strengths and learn from them,” Yung advises. She recalls her early career: “Two teammates were more experienced. Adam, from a graphics background, was quiet but wrote exceptional code and reviews, always spotting design flaws. Mark, with a product and business focus, coded rapidly and anticipated every edge case. I aimed to match Adam’s design and review skills and Mark’s product sense, so I sought extensive code reviews from Adam and user-facing change reviews from Mark.”
Technical Leads: Build a Robust Foundation for Any Path.
After mastering foundational skills, engineers progress to roles like Senior Engineer or Technical Lead. However, Yung cautions against rushing to the next level or into management.
Instead, use these four growth-focused questions to ensure your technical foundation is deep enough for future career moves:
- Do I thoroughly understand the systems I work with, including potential failures and improvements? “This goes beyond surface-level knowledge,” Yung states. “Consider building infrastructure for product launch in one country. Think beyond immediate maintainability to future scalability. What if expansion to ten or a hundred countries is needed? What would break? How would the design adapt? This scenario-based thinking deepens current understanding and strategically prepares for the future.”
- How do I ensure we are working on the most impactful tasks? “Technical leadership isn’t just about problem-solving with scalable, well-designed solutions. The best technical leads also articulate why their work matters and its urgency,” Yung explains. “This doesn’t guarantee perfect judgment, but the best course-correct when necessary.”
- How can I develop stronger people leadership skills? People skills are valuable in any engineering career, regardless of management aspirations. “Take broader project ownership, considering not just technical aspects but also team dynamics—who’s doing what, why, and how they collaborate,” Yung advises. “Mentor interns and new team members to help them grow. Engage cross-functionally, treating PMs and partners as teammates. This builds management readiness and helps determine if management is a desired path.”
Domain Experts: Guard Against Expertise Traps.
Some engineers thrive as domain experts, specializing within a specific area of a company or system. However, it’s crucial to periodically assess continued growth and learning. “If learning stagnates, complacency can set in. Relying on past experience might lead to suboptimal solutions,” Yung warns. “Not only does personal growth halt, but solution quality may decline.”
As you advance, domain expertise may make you feel indispensable. While this might be true, burnout is not worth it, and you likely underestimate your team’s potential.
If you are a domain expert, ask these questions to ensure your expertise is not hindering your or your team’s progress:
- How do I maintain learning and challenge? Recognize signs of stalled growth and seek new inspiration from different people, teams, or systems. “After years in Facebook privacy, I knew how to precisely modify existing infrastructure but lacked new improvement ideas,” Yung recalls. “Looking back, this was a warning sign. The feeling of being essential masked this gap. It was only after merging with a team using a different approach that I felt renewed learning. This led to a system-wide reinvention.”
- How do I demonstrate value when starting anew in a different area? Fear of reduced impact can hinder growth. “Transitioning takes time, but expertise in one area is transferable, and you will likely progress faster and deeper the second time,” Yung assures. A rule of thumb for onboarding experienced hires is one month of initial onboarding for each year in their previous role, followed by rapid impact acceleration.
- How can I effectively transfer knowledge and strategize for future generations? Consider broader knowledge dissemination. “If you’re repeatedly explaining the same thing individually, find a better way. Develop documentation, training, or reusable components for scalable knowledge transfer,” Yung suggests. “Stripe’s culture emphasizes information sharing. However, even in such environments, engineers who could communicate their deep system knowledge effectively were more impactful than those who simply possessed it.”
ADVICE FOR ENGINEERS ON THE MANAGEMENT TRACK: ENHANCING TEAM SUPPORT
New engineering managers face a steep learning curve, compounded by the pressure to maintain technical credibility. Furthermore, measuring people-management success is less tangible than coding output. A common mistake is overcompensating by clinging to coding tasks, often after hours.
Yung advises accepting this shift in focus. “Feeling unproductive and overcompensating with technical work can be incredibly stressful, leading to doubts about the management transition. These feelings can persist, but acting on them prematurely is a mistake. Give it at least six months to a year before re-evaluating,” she recommends.
Instead of focusing on personal contributions, ask these questions as a new engineering manager:
- How healthy is my team? How effective and impactful is our work? New managers can be easily distracted by specific issues or successes. Maintain focus on overall team health and output. “Even with excellent performance reviews, consistent one-on-ones, and manager training, low team performance reduces your overall impact,” Yung points out. Conversely, excessive focus on results can compromise quality and team well-being. “Driving metrics at the expense of team health and developer experience, such as unsustainable on-call rotations leading to burnout, is counterproductive. Balance all aspects of team health, even if short-term changes like prioritizing developer efficiency over roadmap speed seem counterintuitive. Long-term impact will increase.”
- How independently can my team operate? “A former manager gauged his experience level by how long he could be away before his team deviated significantly,” Yung shares. “Initially, it was days, then a week, eventually a month, and longer for paternity leave. His aspiration was a full year. While extended absences may not be practical, it’s a useful benchmark. Managerial growth involves not just knowledge transfer but also building a capable team and addressing gaps. A team might execute tasks quickly but still rely on you for direction and project breakdown. Independence is key for true scalability.”
Experienced Managers: Move Beyond Headcount Expansion.
As managers gain experience, their focus shifts. Project delivery becomes routine, but diminishing returns may set in. Yung notes that many experienced managers over-rely on team growth. “It’s easy to get caught in a cycle of growth and headcount, but this can mask underlying issues and complicate solutions,” she says.
Adding headcount isn’t always the solution. It often creates more problems than it solves.
To progress beyond headcount management, ask these questions to enhance team effectiveness:
- What is my team’s purpose, and why is our work important? “Discuss long-term goals and objectives, not just current projects. Encourage your team to think strategically and suggest alternative paths or challenge existing goals,” Yung advises. “If you can’t articulate the importance of your team’s work, it might be misdirected. Seek feedback and be open to course correction.”
- How can I support the growth of all team members, regardless of experience level or situation? Exceptional managers effectively manage diverse experience levels. Less experienced managers might excel with junior engineers but struggle with senior team members, often due to mutual discomfort. Yung’s advice is to address this directly. “One of my initial team members had twelve more years of experience than me. I was intimidated but decided to learn from it,” she recounts. “In our first one-on-one, I outlined areas where I could contribute (product knowledge, company context) and sought his expertise in areas like managing senior engineers and complex systems. Over time, we built a strong, mutually beneficial relationship.”
ADVICE FOR ORGANIZATIONAL LEADERS: NAVIGATING UNCHARTED TERRITORY
“Transitioning from managing teams to managing organizations feels like a fundamentally new role, similar to the IC-to-manager shift,” Yung observes. “The headcount trap becomes even more pronounced, and the temptation to promote new managers becomes strong. Often, the most reluctant candidates—exceptional technical leaders who prefer not to manage—are the most targeted.”
While urgent situations may necessitate rapid management transitions, Yung advises caution. “Early at Stripe, I transitioned three engineers into management due to immediate needs and a nascent recruiting pipeline. Two thrived, but one realized his passion remained in coding and technical leadership and switched back,” she shares. “The key is to support new managers, ensuring they are well-informed and have opportunities to learn, while also allowing them to revert if management is not the right fit. Keeping unwilling managers in place is costly, burning out valuable team members and preventing the appointment of more suitable leaders.”
Too often, leaders persuade reluctant individuals to become or remain managers, drafting them into service. While sometimes necessary, prolonged misplacement of unwilling managers is a costly error.
Organizational leaders should ask these questions to improve their leadership:
- What is the unifying purpose of your teams, and why are they grouped together? High-growth companies experience frequent reorganizations, shifting between horizontal, vertical, domain-specific, or matrixed structures. This can lead to organizations feeling arbitrarily assembled and lacking a cohesive purpose. “At one point at Stripe, I led teams using specific skills like frontend development, ML, and SaaS business understanding. Initially, it felt like a disparate collection of apps far removed from Stripe’s core business,” Yung recalls. “However, we refocused our mission on enhancing the core payments platform with powerful features for niche but critical users, and pioneering a new, potentially significant business model. This provided a clearer vision and purpose.”
- Are your teams as healthy and effective as possible? Are they structured optimally? Act decisively if team cohesion or purpose is unclear. “Consider broader cross-team improvements. Perhaps a team is redundant, or others are understaffed for critical projects. Seek input from your manager, peers, and cross-functional partners to assess and adjust team structures,” Yung advises. “I assess along these lines: people (right skills and leaders? engagement and growth opportunities?), projects and goals (highest impact work? clear understanding of purpose?), and progress (appropriate pace? high-leverage investments? short-term and long-term acceleration strategies?).”
- Am I effectively engaging with my teams? “Just as technical knowledge aids first-line management, understanding manager and team operations is crucial for organizational leadership. Support each team and gather firsthand insights. Attend team meetings as an observer, conduct skip-level one-on-ones, and communicate transparently,” Yung suggests. However, avoid getting too deep in the weeds. “Over-involvement in team-level issues at the expense of organizational improvements is inefficient. Resist the urge to direct subordinate groups. Now, ‘ask, don’t tell’ is more critical than ever. Rely on group leaders to articulate their needs. Maximize your value by providing broader context and contributing at a higher level.”
Organizational leadership is about support, listening, and coaching, not direct management. Subordinate team members have deeper insight into their daily challenges, making micromanagement low-ROI.
BRINGING IT ALL TOGETHER
Yung summarizes her career growth advice into a concise checklist for engineers:
- Strive to be valuable but not indispensable. Measure your dispensability by assessing team stability in your absence and work to improve it.
- Prioritize learning and growth over rapid advancement. Avoid premature role changes and trend-chasing.
- Cultivate skills for both IC and management roles. Ensure a strong technical foundation for future flexibility.
- Thoroughly prepare for management and understand its emotional demands.
- New managers should focus on team health and impact, not personal coding output.
- Before requesting more headcount, understand team purpose and focus on individual growth.
- As an organizational leader, balance detailed understanding with strategic oversight. Support and coach, don’t micromanage.
Photography by Bonnie Rae Mills. Charts courtesy of Raylene Yung.
