My Journey My Learnings

Khwaja Rasheed
17 min readMar 9, 2024

by Pavni Diwanji for Insurjo24

Humble Beginnings

Starting from a humble background in an Indian middle-class family, I was introduced to computers and programming at an early age, significantly influenced by my father who worked at IBM. This early exposure, coupled with encouragement from my family, particularly as one of two daughters, set me on a technological path.

Educational Journey

I began my educational journey with a Bachelor’s Degree in Computer Engineering from L.D College in the year 1990 where I was the only woman in class. I then advanced to Stanford University for a Master’s degree in Computer Science a move that was as intimidating as it was transformative, surrounded by incredibly talented peers.

Professional Journey:

Sun Microsystems and Java: My first job was at Sun Microsystems, where I worked on projects related to CORBA which, despite failing after two years, led to my involvement in the development of Java, an overnight success that transformed my career, allowing me to grow immensely and become a team leader.

Entrepreneurship and Product Management: My journey continued as I co-founded a search engine startup, which was later acquired by Excite@Home. I also managed the Communication and Client Software division here propelling me into product management. Here, I navigated the challenges of growing a company and managing products faced with issues like spam, which were prevalent at the time.

Returning to Education and Second Startup: The birth of my first daughter led me to pause my career and pursue an MBA at Stanford, following which I co-founded MailFrontier, an anti-spam company, during a challenging time for startups post the dot-com bubble. Despite the difficulties, we managed to secure 3,500 enterprise customers, teaching me valuable lessons in shifting from consumer to enterprise sales.

Google and Beyond: After a sabbatical, I joined Google, spending 14 years contributing to various projects including Blogger and Google Calendar for educational purposes. My time at Google was marked by significant learning, unlearning, and relearning, except for the core values like courage and a can-do attitude. I also worked on Google One, which achieved over a million subscriptions in 2024. I was happy to make an impact by contributing to making Google a safer platform for children through initiatives like YouTube Kids.

Post-Google Career: I took another break to focus on family as my daughter went to college, then joined Intuit and later Meta, where I worked on projects aimed at improving messaging for youth and enhancing parental controls on platforms like Instagram.

Sharing My Three Pillars for Growth

1) Begin:

1. A) Lead and Be Proactive:

Being proactive is about intentionally creating space to reflect and break away from routine. Every few years, I take a step back to explore new ideas and approaches, diverging from my typical work. For instance, during my time at Mail Frontier, I utilized this break to innovate and rethink strategies. Google even institutionalizes such breaks, allowing for creativity and innovation, which led to developments like Gmail.

It’s crucial to feel the urge to act, trust in your capabilities, and lead by example.I encountered firsthand the challenges of inadequate business tools, which spurred me to collaborate with like-minded engineers to develop better solutions, such as Google Apps for Business. This shift in focus from personal projects like Blogger or Calendar to significant enterprise tools demonstrates that navigating the unknown and embracing failure can lead to groundbreaking innovations.

If there is a problem plunge into it and take risk, the bigger the risk the bigger the reward. Working on hard problems gives you the most satisfaction. Also, remember innovation comes from navigating the unknown.

In my journey, I’ve encountered numerous challenges and setbacks. While working on Java at Sun Microsystems, we faced many failed steps before achieving success. Similarly, at Google, we experienced notable failures, such as Google Plus. These experiences taught me crucial lessons about the nature of failure and innovation.

Facing a scary idea or a seemingly insurmountable challenge has always prompted me to step back and engage in a thorough analysis, asking myself “What if it fails?” or “What if it’s only mildly successful?”. This process of writing down and confronting the potential outcomes helps me gain a clearer understanding of the risks involved and prepares me for different eventualities. It’s about assessing the situation, weighing the risks against the potential rewards, and deciding whether the leap is worth taking.

This approach demands a significant amount of courage and foresight. Taking risks is inherently scary, but it’s also a necessary component of innovation and growth. By confronting my fears and considering the full spectrum of possibilities, I’ve been able to make more informed decisions and push forward, even when the path ahead was uncertain. It’s this willingness to face potential failure, learn from it, and continue moving forward that has been a pivotal part of my journey and growth.

1. B) Telling Your Story:

It’s essential to believe deeply in your mission and convey your story simply and authentically. Engaging passionately and frequently with both supporters and critics helps refine your vision and address challenges. I honed this skill through coaching and practice, realizing its importance across startups and established enterprises.

In my experience, effective leadership heavily relies on communication. I emphasize that product and leadership teams should allocate over 30% of their time to engaging with customers, employees, and stakeholders. This approach ensures clarity in vision, facilitates feedback, and strengthens relationships, which are crucial for any project’s success. The higher your position, the more vital your role becomes in maintaining open, transparent communication channels.

This principle has been integral in projects like Google for Kids, underscoring the profound impact that dedicated communication efforts can have on a project’s outcome and team dynamics.

1. C) Well Begun is Half Done:

A recurring theme in my journey has been the significance of acting with urgency and prioritizing user needs. Many ideas fail to materialize simply because they don’t move beyond the ideation phase, largely due to a lack of feature prioritization and a slow approach to development and shipping. Reflecting on the creation of Gmail, the prioritization of core features such as search and storage was instrumental. The goal was to create a product that a few people loved passionately rather than one that everyone just tolerated. This taught me the lesson of urgency: the importance of quickly moving from concept to prototype.

At Facebook, the embodiment of speed was palpable from day one. I was thrust into a boot camp tasked with shipping a complex privacy bug fix within three days. This relentless pace was a testament to Facebook’s culture: what can be done tomorrow should be done today. This approach forced me to adapt quickly, optimize time, and prioritize effectively under pressure.

My experiences have also taught me the importance of maintaining a clear vision while remaining adaptable. During my time at MailFrontier, we developed an application named Matador to filter out spam in Outlook. However, when distribution challenges arose, we pivoted from consumer sales to enterprise sales without abandoning our core vision. This adaptability was crucial for survival and growth.

The tech industry is replete with examples of companies that failed because they couldn’t foresee the future or were too hesitant to invest in it. At Facebook, recognizing the impending dominance of mobile technology led to a pivotal shift where the company momentarily paused other projects to focus exclusively on enhancing the mobile app experience. This decision was based on the understanding that the future was inherently mobile, despite initial resistance and scepticism from the market. Adopting Google’s 70/20/10 innovation framework helped me balance current product enhancements, future-oriented projects, and blue-sky thinking.

Each of these lessons underscores the importance of urgency, user focus, adaptability, and foresight in navigating the complex and rapidly evolving tech landscape. They have been fundamental in my professional development and success.

2) Build:

2. A) Building a Strong Foundational Team and Trust:

Creating an ‘A’ team requires focusing on quality over quantity, where each member not only possesses unique skills but also a shared enthusiasm for the mission. At MailFrontier, we prioritized enthusiasm over experience, which cultivated a culture where anything seemed possible. This approach fostered an environment ripe for innovation and commitment.

The Java team’s success can largely be attributed to its diversity in backgrounds and talents, which brought different perspectives and solutions to the table. This diversity led to vibrant debates and, ultimately, exceptional results. Embracing varied perspectives has been a cornerstone of my teams, leading to richer discussions and more innovative solutions.

Being a servant leader involves putting the needs of the team above your own. This means building shared values and a unified vision, empowering the team for success, and fostering an inclusive and caring environment. Clear and open communication is fundamental to this approach, as it builds trust and encourages team members to contribute their best.

The Google One project, a cross-functional effort with a unified storage quota, faced numerous interventions and roadblocks. Despite these challenges, the project succeeded due to the supportive, transparent nature of the team and the equitable treatment of all members. Conversely, at Facebook, building user trust presented challenges, highlighting the importance of regular forums like Ask Me Anything (AMA) sessions to foster transparency and trust between users and the platform. This underscores the importance of building trust not just within teams but also with the broader user base, a critical component for any product’s success.

2. B) Driving Forward:

At Google, significant emphasis was placed on determining the right metrics even before launching a project. This preemptive approach ensures that all efforts align with measurable goals, facilitating focused and effective progress. But metrics are just one side of the coin; qualitative data, such as user feedback, is equally crucial. Listening to users helps in understanding their experiences, needs, and pain points, which guides better product development and enhancement.

One of the most transformative aspects of Google’s culture is the practice of extreme accountability, especially evident in our postmortem meetings. Here, teams come together to dissect project outcomes without assigning blame. This environment encourages open dialogue, learning from mistakes, and collective responsibility. It’s a holistic approach where accountability is not just an individual’s burden but shared across all levels, promoting a culture of transparency and continuous improvement.

2. C) Developing Best Practices:

In my role as a product manager, developing a clear product roadmap and executing it effectively have been foundational. However, roadblocks are inevitable. The approach I’ve taken involves directly addressing these impediments by engaging with each team member to identify specific obstacles. This collaborative problem-solving starts with understanding individual challenges, followed by collective prioritization to address them systematically. Ownership is critical; it’s not about lending help but about each person taking responsibility for overcoming their hurdles.

Decision-making is a complex yet vital aspect of product management. I’ve learned to consider all available options and evaluate their pros and cons. Recognizing that not all decisions will satisfy every stakeholder, it’s essential to stay grounded in the product’s vision and goals. Transparent communication and justifying decisions with rational evidence have been key in navigating these challenges.

Leading a team through change requires intentionality and empathy. It’s not enough to decide on a new direction; the team needs to understand and support the pivot for it to be successful. This involves clear communication, addressing concerns, and sometimes leading by example. Change management is about guiding the team through the transition, ensuring they understand the reasons behind the change, and securing their buy-in to move forward together. Sometimes, mere implementation without team support can lead to resistance or failure; hence, fostering an environment of trust and open dialogue is crucial for any significant shift in strategy or direction.

3) Grow:

3. A) Scaling the Product and Team:

Scaling correctly is a critical aspect of leadership and organizational development. It’s not just about growing in size but scaling thoughtfully and sustainably, considering the organization’s capacity to handle growth while maintaining high standards.

Before expanding outwardly, it’s essential to ensure that internal structures, systems, and processes can support larger operations. This means assessing the outlook for future projects and initiatives and ensuring that the team can absorb and adapt to this growth without losing effectiveness or efficiency.

Growth should be intentional and aligned with strategic objectives. This includes expanding the customer base, increasing revenues, and structuring the organization to support this growth. However, it’s crucial to avoid the pitfalls of scaling too soon, which can stretch resources too thin, or too late, which can result in missed opportunities.

A fundamental principle in my approach is that the growth of your people should precede the growth of your product. The rationale is simple: a product is only as good as the team behind it. By investing in the development and growth of your team, you ensure that your product also grows in value and relevance. This approach ensures that the team’s skills and capabilities are evolving in tandem with the product’s needs.

Rapid growth, especially in terms of team size, can endanger the company’s quality and culture. This can be mitigated by implementing strong recruiting practices that not only evaluate technical skills but also cultural fit. Fast recruiting, if not managed carefully, can dilute the company’s culture and lower quality standards.

As organizations grow, the operating structure becomes increasingly important. A well-defined structure is vital for clarifying roles, responsibilities, and expectations. This ensures that all team members are aligned and working towards common goals. Effective division of responsibilities is critical to achieving desired outcomes, especially as complexity increases with size.

Sometimes, the initial team that was instrumental in getting the company off the ground might not be the right fit as the company evolves. This is not a reflection of their value or contributions but rather an acknowledgement that different stages of a company’s growth require different skills and perspectives. Recognizing this and making necessary changes, while difficult, is essential for sustained growth and success.

3. B) Developing a Healthy Culture:

Culture encompasses values, missions, processes, rituals, behaviours, and beliefs, reflecting the actions and standards upheld by people within an organization. Though it evolves, core beliefs should remain steadfast.

At Google, the culture is centred around engineering excellence and impactful innovation, guiding our problem-solving approach. As a Product Manager (PM), I recognized my significant role in influencing team culture and product direction, underscoring the importance of leadership in shaping organisational ethos.

Netflix’s perspective — that the essence of a company’s culture is reflected in whom you hire, fire, and promote — resonates deeply with me. It emphasizes the importance of aligning team composition with organizational values, ensuring that the culture reflects the company’s foundational beliefs and objectives.

3. C) Growing Yourself:

Embracing a mindset dedicated to continuous learning has been a cornerstone of my journey. This approach means not just staying updated with the latest in technology and management but also being open to changing one’s self-conception based on new experiences and feedback. This mindset drove me to take on impactful projects, stepping beyond my comfort zone, which in turn accelerated my creativity and problem-solving skills.

Every two to three years, I’ve intentionally sought new challenges and opportunities to pivot, a practice that has been crucial for my growth. For instance, leaving Sun Microsystems was a significant risk, but it revealed to me that my strengths lay more in management than in pure engineering. This kind of self-discovery is vital for personal and professional development. Regularly reassessing my path allowed me to stay aligned with my passions and strengths.

I’ve always been vigilant about the progress I’m making and the environment I’m in. If I notice stagnation or a toxic atmosphere, I don’t hesitate to make a change. This decisiveness is crucial not just for personal well-being but also for maintaining professional integrity and effectiveness.

Thinking ahead has been a critical strategy, especially in leadership roles. Starting with the end in mind and having a clear succession plan ensures that the team or organization can continue to thrive, even in your absence. This approach helps build a robust team and fosters a culture of growth and responsibility among all members.

Having mentors and a supportive professional circle has been invaluable. In every company I’ve worked for, I sought out individuals who could provide guidance, offer a different perspective, and push me towards greater personal and professional achievements. This network has been crucial in navigating challenges and seizing opportunities.

Lastly, my focus has always been on building genuine skills rather than merely crafting an impressive resume. Real skills bring value to teams and projects and contribute to genuine self-confidence and capability, whereas a resume only tells part of the story. This approach has grounded my career in real achievements and continuous improvement.

Finding Opportunities:

Opportunities often present themselves in the least expected ways. My first significant opportunity came through a connection from college. This came at a time when I was seeking change, feeling unchallenged and stagnant in my current role. It’s essential to remain open and receptive to new possibilities, even if they come from unexpected sources.

Sometimes, the best opportunities are those that we create for ourselves. While working on spam tools, I recognized a gap in the market and a need for innovative solutions. This realization pushed me to seize the moment and led to my engagement with Google. It’s about recognizing the potential in your current work and understanding how it can be applied to larger problems or new contexts.

Moreover, my tenure at Google reinforced the practice of dedicating significant time — around 20 to 30% — to scouting for future opportunities. This wasn’t just about staying ahead; it was about ensuring we never found ourselves in a position of complacency or reactive response.

Choosing Between Startups and Big Companies:

When faced with the choice between joining a startup or a larger company, my approach has always been to evaluate the opportunities based on the potential for learning and impact. The decision isn’t merely about the size or the prestige of the company but rather the people I will be working with and what I can learn from them. Can they challenge me? Can they offer a new perspective or expertise that I haven’t encountered before? Furthermore, I assess whether the work I will be doing aligns with my values and whether it has the potential to create a significant impact. This reflective process helps me decide where I can grow more and contribute more effectively, guiding me through various transitions in my career.

Working in India vs Abroad:

The landscape of opportunities has dramatically changed since I moved to the U.S. in 1990. Back then, the U.S., particularly Silicon Valley, was the epicentre of technological innovation and offered unparalleled opportunities for growth and development in the tech industry. However, the global scenario has evolved. Today, India represents a vibrant ecosystem teeming with innovation and entrepreneurship, mirroring the Silicon Valley of the early ’90s. This shift underlines that the decision to work in India or abroad should not be dictated solely by geography. Instead, the focus should be on the opportunities for personal and professional growth available in each environment. The world is increasingly interconnected, and innovation knows no borders. Therefore, whether choosing to work in India or abroad, the priority should be the quality of opportunities and the potential for meaningful contributions and learning.

Reflecting on Corporate Cultures: Google vs. Meta:

Working at both Google and Meta has offered me a unique perspective on how different corporate cultures approach innovation, decision-making, and leadership.

Google’s Culture: Google operates on an intuition-led and democratic basis, fostering a creative and somewhat unstructured environment. This culture encourages employees to ‘see the need and feel the need,’ allowing for a more fluid and organic exploration of ideas. The company’s atmosphere champions creativity, encouraging individuals to propose and develop their innovative ideas. This open and inclusive approach has fostered groundbreaking products and solutions, contributing significantly to the tech landscape and to my personal growth and approach to challenges.

Meta’s Culture: In contrast, Meta is more data-driven, with decisions heavily based on analytics and metrics. The environment is fast-paced and more structured, with a clear top-down approach to decision-making. This provides a different kind of clarity and direction, pushing for rapid development and deployment of ideas. The emphasis on data and speed has honed my ability to make quick, informed decisions and adapt to a constantly evolving market.

Both environments have their merits and have significantly shaped my professional outlook. Google has nurtured my ability to think outside the box and championed the freedom to explore new ideas. In contrast, Meta has fine-tuned my analytical skills and decision-making speed, teaching me the value of structure and fast execution.

On Mentorship:

The significance of mentors in my journey cannot be overstated. My father, serving as my first and most enduring mentor, introduced me to the world of programming and instilled in me the fundamentals of problem-solving and critical thinking. His guidance was not just about coding; it was about understanding the essence of perseverance, curiosity, and the joy of discovery. He used to take me to work with him at IBM, where I first interacted with computers, playing with punch cards and marvelling at the machinery. This early exposure was pivotal, laying the foundational stone for my career.

Beyond familial guidance, my professional journey was significantly shaped by mentors like Anita Borg. While at Sun Microsystems, I had the privilege of volunteering for Borg outside of my regular duties. She was not just a mentor but a beacon of inspiration, exemplifying strength, intelligence, and the unyielding pursuit of one’s passions against all odds. Her commitment to advancing women in technology and her visionary outlook profoundly influenced my aspirations and my approach to challenges.

These mentors, among others, provided me with more than just knowledge; they offered wisdom, encouragement, and the crucial understanding that success comes from perseverance, learning from failures, and constantly challenging oneself. Their diverse perspectives helped me navigate the complex landscapes of technology and leadership, shaping me into the person I am today.

Life Beyond Work

When not engrossed in technology, I indulge in painting, a passion that complements my love for travel and adventure. These activities provide me with a fresh perspective and a creative outlet, enriching my personal and professional life.

Conclusion:

In concluding my journey and sharing the lessons learned along the way, I extend a special message of inspiration to emerging women leaders, especially those navigating the vast and ever-evolving landscape of technology:

Be crazy about your vision and mission: Let your passions and aspirations guide you, and pursue them with relentless energy. The path less travelled by women in tech is ripe with opportunities to make a significant impact.

Be bold in your beginnings: Venturing into new territories, especially in a field where women are underrepresented, demands courage and resilience. Your boldness to start despite the odds is what will set you apart and pave the way for others.

Hold steadfast to your values and culture: In an industry that’s constantly changing, your core values and the culture you foster will be your unwavering pillars. They will guide you through challenges and help you make decisions that reflect your true self.

Execute with responsibility and impact: As you innovate and lead, do so with a consciousness of the broader implications of your work. Strive to create technology that enriches lives, fosters equality, and empowers communities.

Commit to continuous growth: The journey of learning never ends, especially in technology. Embrace every opportunity to grow, not just as a leader or technologist, but as a mentor and role model for other women aspiring to make their mark.

And to all the emerging women leaders in technology, remember this cherished quote:

“The people who are crazy enough to think they can change the world are the ones who do.” — Steve Jobs

This quote is a beacon for those who dare to dream big. Your presence in tech is not just about filling a gap; it’s about reshaping the future, bringing diverse perspectives to the forefront, and creating solutions that reflect the needs of all humanity. Let us be the ones who challenge the status quo, break barriers, and open doors for generations of women to come. Together, we have the power to change the world. Let’s be bold, be visionary, and above all, be unstoppable.

The content was taken from my notes for the Insurjo24 session of Pavni Diwanji, ex-VP of Facebook and Google.

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Khwaja Rasheed

Life depends on Your Interpretation of it! I am crafting an interesting story out of it :)