Leadership

13 Leadership Tenets From My 15-Year Tech Journey

Howard Profile

Howard Ekundayo

November 2, 2024

13 Leadership Tenets From My 15-Year Tech Journey

Throughout my career spanning Goldman Sachs, Google, Netflix, OpenAI, and co-founding Onramp, I've collected principles that have guided me through successes, failures, and everything in between. These aren't theoretical concepts from management books—they're hard-earned insights from building products, leading diverse teams, and navigating complex organizational landscapes. I'm sharing these tenets in hopes they might serve others on their own leadership journeys.

1. Strong Leaders Model, Delegate, and Sponsor

Early in my career at Goldman Sachs, I mistakenly believed leadership meant having all the answers. By the time I became an Engineering Director at Netflix (and then Google), I'd learned that effective leadership requires three distinct modes of operation, each essential in different contexts.

Modeling means demonstrating the behaviors and standards you expect. During my first stint at Google, I co-founded the Google Howard West program. As an Engineering Lead, I didn't just talk about inclusive mentorship—I showed it by co-developing curriculum and teaching software engineering courses myself. Teams quickly detect disconnects between what leaders say and what they do.

Delegation isn't about offloading work—it's about creating growth opportunities while maintaining accountability. At Netflix, I learned to delegate not just tasks but outcomes, giving team members both responsibility and authority. This required being explicit about constraints while avoiding micromanagement.

Sponsorship means actively advocating for your people when they're not in the room. This became particularly clear while leading ChatGPT's core experiences team at OpenAI. In high-stakes environments, your willingness to put relational capital on the line for your team members determines whether talented people stay and thrive. True sponsorship means taking risks on people you believe in.

"The mark of a great leader isn't the number of followers, but the number of leaders they create. This happens through the deliberate practice of modeling, delegation, and sponsorship—often simultaneously."

2. Tech is the Matrix; Some Rules Can Be Bent, Others Can Be Broken

The technology industry operates with both explicit and implicit rules. Understanding which ones are flexible and which are inviolable separates those who make incremental progress from those who drive transformational change.

At Google, I observed how some teams remained constrained by conventional thinking about what was possible or permissible, while others questioned fundamental assumptions and created breakthrough products. The rules that can be bent typically involve process, organizational structure, and conventional wisdom about user behavior.

However, some rules cannot be broken: ethical principles, legal requirements, and commitments to users about privacy and security. At OpenAI, we constantly navigated this tension—pushing boundaries of what AI could do while establishing guardrails around responsible deployment.

This tenet isn't about recklessness—it's about discernment. Leaders must develop judgment about when rule-breaking represents necessary innovation versus dangerous corner-cutting. This discernment only comes through experience and maintaining strong ethical foundations.

3. It's All Monopoly Money. Save and Invest It While You Can

The tech industry can create illusions of perpetual abundance. High salaries, generous equity packages, and lavish perks can make it easy to develop spending habits that become difficult to sustain through market downturns or career transitions.

When I joined Netflix after years at Google, I experienced firsthand how quickly compensation structures and company valuations can change. Later, when I left a stable role to co-found Onramp, I appreciated having built financial resilience that allowed me to take calculated risks.

This principle extends beyond personal finance to how we approach resources within organizations. At OpenAI, we made difficult resource allocation decisions, recognizing that even well-funded companies must prioritize investments based on mission alignment and potential impact.

Treat compensation as a tool for creating optionality and resilience, not just immediate comfort. Build habits of saving and investing during abundant times to create freedom during challenging periods or when mission-driven opportunities arise that may not maximize short-term compensation.

4. The More Senior the Role, The More Challenging and/or Empowering Identity Politics Can Be

As a Black engineering leader who has progressed through increasingly senior roles, I've experienced firsthand how identity becomes simultaneously more challenging and potentially more empowering as you ascend organizational hierarchies.

At junior levels, technical capabilities often take center stage. As you move into leadership positions where subjective judgment and cultural fit factor more heavily into advancement, the dynamics of identity become more pronounced. This creates both challenges and opportunities.

The challenges are real: research consistently shows that underrepresented leaders face greater scrutiny and higher standards. When leading international engineering teams at Google, I navigated complex dynamics where my identity sometimes created additional hurdles for establishing credibility and influence.

However, this same dynamic creates opportunities for impact. As Chairman of the National Science and Technology Medals Foundation board, I've seen how leaders from underrepresented backgrounds can leverage their perspectives to drive positive change in STEM fields. Our unique vantage points allow us to identify blindspots in product development, organizational design, and talent development.

This tenet isn't about dwelling on challenges but recognizing reality: identity becomes more salient, not less, as leadership responsibility increases. Effective leaders acknowledge this dynamic while refusing to be limited by it.

5. Bet on Yourself, Always

Throughout my career, the highest-return investments have consistently been those I've made in myself—whether through education, relationship-building, risk-taking, or creating space for reflection and growth.

When I left Google to co-found Onramp, many questioned whether stepping away from a prestigious role to build an EdTech startup was wise. But I believed in our mission to connect underrepresented talent with life-changing software engineering careers. The skills, relationships and perspective I gained during that journey have proven invaluable throughout my subsequent leadership roles.

Similarly, when I left a director position at Google to join OpenAI, I was betting on my ability to add value in a rapidly-evolving space despite the uncertainties involved. These decisions weren't about blind self-confidence but about recognizing that investing in expanding my capabilities and experiences would yield returns regardless of how any specific role unfolded.

Betting on yourself means seeking growth over comfort, impact over status, and long-term development over short-term optimization. It means trusting your capacity to learn, adapt, and create value in changing circumstances.

6. Always Be the Employee "That Got Away"

How you leave an organization reveals as much about your character as how you lead within it. Throughout my transitions—from Goldman Sachs to Google, from Google to Netflix, and beyond—I've focused on departing with such professionalism and integrity that former employers and colleagues would welcome my return.

Being the employee "that got away" means:

  • Providing generous transition periods and comprehensive knowledge transfer
  • Expressing genuine appreciation for the opportunities you received
  • Maintaining relationships after departure
  • Speaking respectfully about former employers even when discussing challenges
  • Continuing to champion and support former colleagues

When I left my first stint at Google, I maintained strong relationships that eventually facilitated my return as a Director years later. The tech industry is smaller than it appears, and reputation follows you throughout your career. Create such positive impressions that organizations feel they've lost something valuable when you depart.

"Your departure story becomes part of your professional narrative. Write it with the same care and intention you bring to your work. Make them miss you when you're gone."

7. Protect Your Integrity at All Costs. Don't Burn Bridges. Take the High Road

In technology's high-stakes, fast-paced environment, difficult situations inevitably arise: disagreements with leadership decisions, conflicts with colleagues, or organizational changes that feel unfair. How you respond in these moments defines your character and shapes your long-term influence.

Integrity means maintaining consistent ethical standards even when doing so is inconvenient or costly. At Netflix, I faced situations where short-term business objectives created tension with long-term ethical considerations. Choosing integrity sometimes meant advocating unpopular positions or accepting temporary setbacks to uphold deeper principles.

Not burning bridges requires emotional regulation and strategic patience. When I've disagreed with decisions, I've worked to understand underlying motivations, express concerns constructively, and maintain productive relationships even in disagreement. This approach preserved influence and created opportunities for impact that would have been impossible had I opted for burning bridges.

Taking the high road isn't about avoiding conflict—it's about engaging with difficulties in ways that reflect your best self. It means responding to challenges with maturity, empathy, and a long-term perspective rather than reactive emotion.

Together, these principles form a foundation for sustainable leadership influence that transcends any single role or organization.

8. If You Have a Good Manager, Protect Them

Exceptional managers who combine technical expertise, emotional intelligence, and genuine concern for their people's growth are rare treasures in the technology industry. When you find yourself reporting to such a leader, recognize your responsibility to support and protect them just as they support you.

Early in my career at Goldman Sachs, I benefited tremendously from a manager who created growth opportunities, provided honest feedback, and shielded our team from organizational politics. I learned that this protection wasn't one-directional—the most effective teams create virtuous cycles where managers and reports mutually reinforce each other's success.

Protecting good managers means:

  • Delivering outstanding work that reflects well on their leadership
  • Providing upward feedback that helps them improve
  • Managing information flow judiciously rather than escalating every challenge
  • Publicly supporting their decisions while discussing concerns privately
  • Expressing appreciation for their investment in your development

When I became a manager myself, I recognized how fundamentally team members influenced my effectiveness. The teams that thrived were those where protection flowed in all directions—creating environments of mutual trust that magnified everyone's impact.

9. Giving Constructive Feedback Builds Trust

Perhaps counter-intuitively, I've found that relationships strengthen not through constant affirmation but through the vulnerable exchange of constructive feedback. Organizations where honest feedback flows freely consistently outperform those where difficult conversations are avoided.

At Netflix, I inherited a team culture where direct feedback was sometimes avoided to maintain surface-level harmony. By modeling specific, actionable, and compassionate feedback—starting with inviting criticism of my own leadership—we transformed into a high-performing organization where trust deepened through honesty.

The key insight is that withholding feedback ultimately communicates lack of investment in someone's growth. When we care deeply about colleagues' development, we accept the discomfort of difficult conversations because we recognize their long-term value.

This principle extends beyond individual relationships to organizational health. Teams that normalize constructive feedback create environments where problems surface early, continuous improvement becomes cultural, and trust compounds over time.

10. "Users" of Products at Scale Include Regulators

When building technology that reaches millions or billions of people, the definition of "user" must expand beyond individuals interacting directly with your product. Regulators, policymakers, and governance bodies become crucial users whose needs and concerns must be anticipated and addressed.

At Google, I witnessed how products designed purely for consumer delight without considering regulatory perspectives often faced challenges that could have been avoided through more expansive thinking about stakeholders. This principle doesn't suggest compromising product quality or innovation. Rather, it recognizes that sustainable innovation requires understanding the broader ecosystem in which technology operates. Product teams that proactively consider regulatory perspectives often develop more robust, resilient solutions that create lasting value.

Practically, this means:

  • Including policy expertise in product development processes
  • Designing with transparency and explainability in mind
  • Creating robust documentation of decision processes
  • Building flexibility into systems to accommodate evolving requirements

The teams that thrive long-term are those that expand their definition of success beyond immediate user metrics to include sustainable operation within evolving regulatory frameworks.

11. Understand the Why

In complex organizations, instructions and strategies often get communicated without their underlying rationale. Leaders who excel are those who persistently seek to understand not just what needs to be done, but why it matters in the broader context.

When I led an international engineering organization at Google focusing on Search experiences, understanding the "why" behind product priorities enabled my team to make better autonomous decisions, identify creative alternatives when obstacles arose, and maintain motivation through challenging implementation difficulties.

Understanding the "why" operates at multiple levels:

  • Strategic why: How does this initiative connect to company mission and business objectives?
  • User why: What human needs or problems are we addressing?
  • Technical why: What principles guide our implementation approach?
  • Organizational why: Why is this team structured this way for this challenge?

Leaders who habitually ask "why" develop deeper understanding that enables them to communicate more effectively, adapt more intelligently when circumstances change, and build more meaningful alignment across diverse stakeholders.

"The difference between compliance and commitment is understanding the 'why.' Teams that grasp the deeper purpose behind their work consistently outperform those simply following directions."

12. Even the Playing Field

Throughout my career, I've observed how uneven access to information, opportunities, and resources creates environments where talent alone doesn't determine outcomes. Leaders have both the power and responsibility to create more equitable conditions that benefit organizations and individuals alike.

This principle animated my work co-founding Onramp, where we built pathways for talented individuals from non-traditional backgrounds to access life-changing careers in software engineering. We recognized that interview processes and hiring criteria often reflected privilege rather than potential.

Within organizations, evening the playing field means:

  • Ensuring equitable access to high-visibility projects and growth opportunities
  • Creating transparent promotion criteria and processes
  • Democratizing access to context and information
  • Building inclusive interview processes that assess genuine capability
  • Designing compensation structures that reward impact rather than negotiation skill

As Chairman of the National Science and Technology Medals Foundation board, I've continued this work by supporting underrepresented scholars in STEM and recognizing diverse innovators. Creating level playing fields isn't just morally right—it unlocks organizational performance by ensuring the best ideas and talents can emerge regardless of background.

13. On Difficult Days, Listen to Katy Perry's Greatest Hits - Trust Me

This final tenet might seem lighthearted, but it addresses something profound: resilience requires deliberate emotional regulation strategies. Throughout leadership challenges—layoffs at Google, surprisingly low performance ratings, difficult conversations with team members—I've learned that intentional mood management is essential.

Katy Perry's anthems of resilience and self-empowerment like "Roar," "Firework," and "Rise" might seem unlikely management tools, but they represent something crucial: leaders need personal practices that restore perspective and emotional equilibrium during challenging periods.

Whether through music, physical activity (like my CrossFit training), meditation, or other practices, effective leaders develop self-regulation strategies that prevent temporary setbacks from becoming derailing spirals. This emotional management isn't self-indulgent—it's essential for sustainable leadership.

The deeper principle here is that leadership requires emotional stamina alongside technical and strategic capabilities. Developing personal resilience practices isn't optional but foundational for long-term effectiveness.

Bringing It All Together

These thirteen tenets haven't emerged from theoretical study but from navigating real challenges across different organizations, roles, and seasons of my career. They reflect both mistakes I've made and successes I've experienced while building products, managing teams, and leading organizations at Goldman Sachs, Google, Netflix, OpenAI, and beyond.

What unites these principles is a holistic view of leadership that encompasses technical excellence, interpersonal wisdom, and personal well-being. The most effective leaders integrate these dimensions rather than excelling in just one arena.

I share these tenets not as fixed commandments but as evolving insights that continue to develop through new experiences. The greatest leaders remain perpetual students—constantly refining their understanding through reflection, feedback, and fresh challenges.

As you navigate your own leadership journey, I encourage you to develop tenets that reflect your unique experiences and values. The specific principles matter less than the deliberate practice of extracting wisdom from experience and applying it to future challenges. This reflective leadership approach transforms even difficulties into opportunities for growth and impact.

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