Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox, and if you want to read more of my posts, check out my archive here!

Today, in 5 Minutes or Less 🕰️

In this issue, we'll explore the typical career paths for aspiring design leaders in tech, demystify the firm foundation you need to start your journey to the top job.

Did You Know 😊

The "10-year rule" for mastering a skill is a well-known concept, but in the tech industry, the timeline for design leadership is a pressure cooker. While your counterparts in traditional sectors may spend decades slowly climbing the corporate ladder, you need to prove your strategic value and business acumen at lightning speed. It's not uncommon for design leaders to secure an executive or senior leadership role within their first 10-13 years of their career. This compressed clock means every year counts, and every decision is a critical step toward the top. To position yourself for a top leadership role, you need to be intentional and strategic at each stage.

Years 1-5: Foundational Excellence: This is your time to become a master of your craft. Hone your skills in a core discipline, build a strong portfolio, and gain a deep understanding of the technology and business you're designing for.

Years 5-10: Expand Your Influence: Shift your focus from individual contribution to team and project/product leadership. Seek opportunities to manage projects and teams, contribute to product strategy, and build strong cross-functional relationships. Learn to connect your work to the bottom line. Job titles and focus might evolve like this:

Individual Contributor: Your focus is on execution of design tasks, the quality of individual output and personal craft and skill development.

Design Manager: You focus on team impact and output, individual growth, developing team members, project oversight.

Design Director: You focus on departmental strategy, cross-functional alignment, operational excellence, scaling functional  impact.

VP/C-level Design Leader: You focus on company-wide design strategy, organizational impact, business growth, future-proofing design, and executive advocacy.

✍ Case Study: Moi!

🍏 The Foundation: Deep Craft at Apple

I started my career straight out of college as an Interaction Designer in Apple's Advanced Technology Group (ATG). I spent three years honing my craft, learning from some of the best minds in the industry. My first management moment came when I was asked to lead an interdisciplinary team researching omnidirectional display technologies. It was my first taste of management—not by choice, but by necessity—and it set the stage for everything that followed.

💻 The Hustle: Agency Life and Startup Scraps 

After five years Apple closed ATG and I joined the design agency Studio Archetype as an Interaction Design Director. Then I moved to Excite@Home as a Principal Interaction Designer. This was over a two year time span where I learned to adapt to different environments, navigate immigration challenges, cope with my father passing away, buy my first house… you get the picture. It taught me resilience, tenacity and adaptability and so much more that would prove invaluable as I grew up personally and professionally.

🚀 The Leap: Scaling a Team at Yahoo 

Seven years into my career, I was given a huge opportunity: to become Yahoo's first Design Manager. Over the next five years, my role and responsibilities grew exponentially. I helped build and scale projects and teams, and connected design outcomes directly to business results. I left Yahoo as a Senior Director, taking a much-needed career break. After 12 years of being an immigrant ‘alien of extraordinary ability’ where my right to be in the U.S. was tied to my visa, I had finally secured my green card and applied for U.S. citizenship

🧘‍♀️ The Detour: A Break to Build Something New 

My career then took a fascinating six-year detour. I leveraged the principles of user-centered design thinking in a completely different context: running my own Feng Shui consulting company. I immersed myself in Chinese metaphysics, a discipline that taught me new ways to look at systems, patterns, and human experience from the outside in. I know what you might be thinking, why not something practical or monetizable, like an MBA? Go figure!

💡The C-Suite: Back to Tech with a Fresh Perspective 

My unconventional career path came full circle when I returned to the tech world to build a UX design team for the startup, [24]7.ai. The skills I'd developed during my break—systems thinking, pattern recognition, and a fresh perspective on human-centered design—were crucial. They empowered me to build a cross-functional, international design teams from the ground up.

Over the next five years, I rose to become the company’s Chief Design Officer. After that, I spent a year as a Director of Product Design at Meta before starting my own coaching company. This new chapter allowed me to shift my focus to the human experience from the inside out, and I now dedicate my time to supporting the next generation of creative leaders in tech as they navigate their own unique leadership journeys.

🤑 How to Apply This 

My story isn't a playbook, but a reminder that a leader's career isn't always a linear climb. The moments that seem like detours, the layoffs, the side hustles, the career breaks are often where the most profound growth and unique skills are forged. It's these diverse, often difficult, heart wrenching experiences that truly set great leaders apart. A journey into leadership, I found, requires a lot of introspection and learning. Two learnings I came to see were essential to leadership are nurturing allies and being an active listener. Here’s why:

🕸️ Build and Nurture Allies and Supporters

Your leadership is ultimately measured by the trust others place in you. The most powerful proof of your influence is not what you say about yourself, but what others say on your behalf to those in power when you are not in the room. Your network is more than a list of contacts; it's a living ecosystem of support. Engage with people, learn about them and find your tribe.

👂 Practice Active Listening

In a heated debate with engineering and product teams about a critical feature, it's easy to get defensive and immediately jump to protecting your team's work. An active listening approach offers a powerful alternative.

Active listening is about understanding perspectives, asking clarifying questions, and reflecting on what's been said. Instead of reacting defensively, you could pause and ask, "What are the core concerns from engineering about the timeline, and from product about the user value?"

Their responses will help you identify common ground and propose a solution that respects everyone's constraints and priorities. This strategy not only builds consensus rather than creating conflict, but it also establishes a foundation of trust.

💥 The Short Of It 

The path to the executive suite is less about a linear climb and more about a strategic expansion of your skills, influence, and network. The key is to see every experience, conventional or not, as a story of continuous growth, and the time to start writing your next chapter is now.

On that note, I have to be honest this newsletter took a longer break than I intended. The reason? I've been writing my first book! I'm so excited to finally share that I've completed "Leading by Design: The Insider’s Playbook for Tech Leadership," which is coming out this September. I poured everything I know into this project and can't wait to share more details with you in the coming weeks.

That's it for this week!

If you enjoyed this piece, subscribe to get the next one in your inbox, and check out my archive here.

Are there any topics you’d like me to cover in the future? Just send me a direct message or an email.

With ❤️ from Sally

PPS Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Claim your free copy of the Personal Planning Workbook "Sally's Soul Searching Research Guide” and discover how to unlock purpose and direction in the areas of your life that are in your control.

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics