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From the structured corporate halls of Microsoft to the hyper-growth environment of Meta, and now to the cutting-edge frontier of AI at Anthropic, Fiona Fun’s career trajectory offers a masterclass in engineering leadership. Her journey highlights how engineering cultures evolve, how leaders must adapt their styles as they scale, and why human connection remains central to technical success.
Navigating the transition from an Individual Contributor (IC) to a Manager of Managers requires a shift in mindset—from solving code to solving organizational friction. Based on her extensive experience across three of the world’s most influential tech companies, Fun provides actionable insights on dogfooding products, structuring mentorship, and the critical soft skills that define top-tier engineering leaders.
Key Takeaways
- Adaptability is crucial: Engineering velocity varies wildly between companies; success requires adjusting from four-week sprints (Microsoft) to weekly updates (Meta) to rapid AI iterations (Anthropic).
- "Trust but Verify" enables scale: As a manager of managers, you must delegate without losing touch with the product's reality.
- Dogfooding is a leadership tool: Using your own product builds empathy, accelerates bug fixes, and earns respect from your engineering team.
- Separate status from connection: Effective one-on-ones should focus on career growth and blockers, moving status updates to asynchronous channels.
- Listen before you debug: When receiving feedback, resist the engineer’s urge to analyze immediately; simply listen, absorb, and reflect later.
The Evolution of Engineering Speed and Culture
One of the most distinct differences between tech giants is their operational cadence. Fun notes that moving from Microsoft to Facebook (now Meta) exposed a drastic shift in velocity. While traditional software development might rely on month-long sprints, hyper-growth environments often operate on weekly cycles.
This speed, however, brings its own set of challenges. High-stakes projects—often termed "War Rooms" or lockdowns—can drive immense focus and rapid delivery, but they come with a cost.
Managing the "War Room" Dynamic
Concentrated periods of intense work can align a team toward a singular existential goal. However, leaders must be vigilant about the trade-offs regarding team health. Fun reflects that while lockdowns successfully block out distractions, prolonging them without realistic timelines can damage morale.
Effective leaders must hold deliberate trade-off discussions. If a growth goal requires a two-month "sprint," leadership must be transparent about the duration and the toll it takes, rather than letting a short-term crunch evolve into a permanent state of emergency.
The "Ownership" Mindset
A defining characteristic of high-performance cultures is the dissolution of boundaries regarding responsibility. At Meta, the mantra "nothing is someone else's problem" created an environment where engineers leaned in to solve issues regardless of their specific role. This collective ownership fosters a tighter feedback loop and ensures that critical problems aren't ignored simply because they fall outside a specific job description.
Mastering the Transition to Engineering Management
Scaling from a frontline manager to a manager of managers introduces new complexities. The relationship shifts from managing code output to managing the people who manage the output.
Trust but Verify
A common pitfall for new leaders is over-delegation, which can lead to a disconnect from the ground truth. Fun advocates for a "trust but verify" approach. This does not mean micromanagement, but rather maintaining enough visibility to ensure projects are on track.
"I think sometimes you might also hear advice of 'delegate so it could scale up.' If you delegate too much but don't do the 'trust and verify,' you lose touch with a project a little bit too much."
Leaders must encourage radical transparency to avoid the "This is fine" scenario—referencing the popular meme of a dog in a burning room. If managers hide problems to appear competent, leadership cannot provide the necessary support to put out the fires.
Mentorship vs. Coaching
Many leaders conflate mentorship with coaching, but distinguishing between them can lead to more effective growth conversations:
- Mentoring: The sharing of life experiences, specific advice, and resources. It is directive and additive.
- Coaching: Acting as a mirror. The goal is to help the individual discover answers within themselves through questioning and reflection.
For these relationships to work, the mentee must drive the agenda. Setting explicit goals—such as defining what success looks like after three or six months—ensures the time is valuable for both parties.
The Strategic Value of Dogfooding
For engineering leaders, "dogfooding" (using your own product) is not merely a Quality Assurance task; it is a strategic leadership activity. Fun argues that when leaders actively use the product, it signals to the team that the work matters.
Building Empathy and Urgency
There is a tangible difference in bug resolution speed when a leader experiences a glitch personally. When an Engineering Director reports a broken feature, it cuts through the backlog noise and highlights the issue's severity. This practice also serves as "maker time" for managers who no longer code daily, allowing them to contribute to product quality tangibly.
Whether it was selling items on Facebook Marketplace to understand the seller flow or using VR headsets for workouts, integrating the product into daily life reveals friction points that standard testing scripts miss. At Anthropic, this culture persists as "Ant-fooding," where internal teams use models like Claude Code to build their own tools, creating a rapid feedback loop between usage and development.
Soft Skills: The Bedrock of Leadership
Beyond technical acumen, the ability to connect with people and navigate difficult conversations defines a leader's legacy. This becomes even more critical in remote or hybrid environments.
Optimizing One-on-Ones
One of the most common inefficiencies in management is using one-on-one time for status reporting. Fun advises moving all status updates to asynchronous channels, such as Slack or a living document. This liberates meeting time for high-value conversations: career development, curiosity-driven discussions, and deep dives into complex product decisions.
The Art of Receiving Feedback
Engineers are trained to debug problems immediately. However, applying this "debug mindset" to personal feedback can be counterproductive. When receiving constructive criticism, the instinct to ask clarifying questions often feels like defensiveness or an attempt to justify behavior.
"When someone cares enough to come to you for constructive feedback, it's already uncomfortable enough... Make sure that first session you're just in read-only mode just to learn and listen."
The best approach is to listen, thank the person, and wait 24 hours to process the information before asking follow-up questions. This ensures the psychological safety of the person giving feedback.
Leading with Kindness
In high-pressure environments, kindness is a strategic asset. During the COVID-19 pandemic, the importance of empathy became undeniable. Leaders often do not know the personal struggles their teams face outside of work hours. A simple act—like rescheduling a meeting to allow an employee to FaceTime a relative—can build immense trust and loyalty.
"In a world where you can be anything, be kind."
Conclusion
From the structured development of Visual Studio to the generative frontiers of Anthropic, the core tenets of engineering leadership remain consistent: transparency, empathy, and a relentless focus on product quality. Whether managing through a "War Room" or guiding a team through a paradigm shift in AI, the most effective leaders are those who stay connected to the work and deeply committed to their people.
As the industry accelerates, Fun’s advice to her younger self resonates for engineers at any stage: "Enjoy the ride. These are the good old days." In the rush to ship the next feature, pausing to appreciate the innovation and the team building it is essential for long-term fulfillment.
