Leadership Archives

January 5, 2025

Strategic Design Leadership: Essential Questions for Design Executives

Design leaders face a pivotal moment. As artificial intelligence reshapes creative processes, platforms evolve at unprecedented speed, and businesses seek more profound competitive advantages, the mandate for design leadership has fundamentally expanded. What was once about craft excellence and product impact now demands enterprise-wide transformation and strategic influence.

Yet, with expanded influence comes increased complexity. Today's design executives must simultaneously:

Drive business transformation while preserving creative excellence
Scale impact across portfolios while maintaining quality and consistency
Navigate emerging technologies while focusing on human needs
Build organizational capability while delivering immediate results
Create measurable business value while pursuing breakthrough innovation

Success in this environment requires new frameworks for thinking and action. The questions that follow serve as a strategic compass for design executives navigating these challenges. Developed through observation of leading design organizations, they target the core dimensions that distinguish high-performing design leadership: vision that drives transformation, systems that enable scale, teams that deliver excellence, and innovation that creates lasting value.

These are not questions to answer once and move on. They are tools for continuous reflection and strategic clarity - helping design leaders maintain focus on what matters most while building the foundations for lasting impact.

Direction-Setting: Drive Design-Led Transformation

Vision & Strategy

Do we have a compelling vision for how design will transform our business beyond improving products?
Have we clearly articulated how design drives core business metrics and enables future growth?
Are we making bold bets that position design as a strategic driver rather than just a service function?
Have we redefined what unique value design brings in an AI-augmented world?
Are we positioned to shape business strategy, not just respond to it?

Innovation Direction

Are we leading breakthrough innovation initiatives that could fundamentally transform the customer experience?
Have we identified clear opportunities where design can create competitive advantages that are difficult to replicate?
Are we effectively balancing short-term execution with long-term transformation?
Are we driving innovation in business models, not just user experiences?
Have we identified opportunities where design + AI can create exponential value?

Resource Allocation

Are we investing our design resources in the highest-impact opportunities across the company?
Have we identified and secured resources for strategic capabilities we need to build for future success?
Are we systematically reallocating resources from lower to higher-value design initiatives?
Have we created clear mechanisms to scale design impact without linear headcount growth?
Are we investing ahead of emerging competitive threats and opportunities?

Organizational Alignment: Scale Design Impact

Organizational Design

Does our organization structure enable both consistent execution and rapid innovation?
Are we building mechanisms to scale design thinking across the enterprise?
Have we structured for agile learning and adaptation versus traditional workflows?
Does our organization enable both strategic influence and operational excellence?

Talent & Capabilities

Are our most critical design roles filled with exceptional talent who can drive strategic impact?
Are we developing leaders who can drive enterprise transformation through design?
Have we redefined career paths for an AI-augmented design world?
Are we building the commercial and strategic acumen our future requires?
Have we identified and developed new capabilities needed for strategic impact and future success (e.g., AI integration)?

Design System Evolution

Is our design system evolving from a component library to a true strategic asset?
Are we building infrastructure that creates network effects across products?
Have we established frameworks for maintaining quality in an era of infinite variation and rapid generation?
Are we effectively balancing standardization with AI-enabled personalization?

Leadership Mobilization: Build Strategic Influence

Senior Team Evolution

Have I built a senior leadership team that balances design excellence, business acumen, and strategic thinking?
Does my team reflect the diversity of perspectives needed across customer experience, systems thinking, and technological innovation?
How have I developed my leaders from execution-focused managers to strategic partners who can influence at the enterprise level?
Is our design leadership team equipped to shape business strategy?
Have we developed the judgment to lead in an AI-augmented world?

Team Dynamics & Decision-Making

Does our leadership team operate as a cohesive unit focused on enterprise-wide impact rather than just portfolio-specific wins?
Are we having the right strategic conversations that elevate beyond craft and into business transformation?
Are we making decisions at the pace our technology enables?
Have we created mechanisms for cross-functional strategic influence?
Is our team equipped to shift from production excellence to strategic judgment?
Have we established clear principles for when to preserve human craft versus leverage AI capabilities?

Operating Rhythm

Have we established a cadence that balances strategic thinking with rapid execution?
Are our leadership forums and rhythms driving substantive strategic discussions versus status updates?
Have we evolved our rituals to focus on strategic impact versus production?
Are our review processes suited to AI-accelerated workflows?
Do we have the right forums for influencing enterprise direction?

Cross-Organization Leadership

Has my senior team built the right relationships and influence with cross-functional leaders?
Are we effectively bridging between design excellence and business impact in our leadership approach?
How are we developing the next generation of strategic design leaders?

Innovation Excellence: Drive Breakthrough Impact

Customer-Centered Innovation

Are we identifying opportunities that transform customer relationships?
Have we created effective mechanisms to translate customer insights into innovation?
Are we effectively balancing user needs with business objectives?
Do we have frameworks for innovation that leverage both human and machine capabilities?

Technology Integration

Are we effectively integrating emerging technologies into our design processes?
Have we established clear frameworks for evaluating and adopting new design tools?
Are we maintaining design excellence while leveraging automation and acceleration?
Have we defined clear principles for human-AI collaboration in design?
Have we built infrastructure that scales our strategic advantages?
Are we effectively balancing automation with human judgment?

Measurement & Impact

Have we established new metrics for design's strategic impact?
Are we measuring value creation beyond traditional design metrics?
Do we have clear frameworks for evaluating AI-augmented design quality?
Have we created mechanisms to demonstrate design's enterprise value?

Personal Effectiveness: Lead with Vision and Craft

Time & Focus

Am I spending enough time on strategic priorities versus operational details?
Have I created effective delegation mechanisms for routine decisions?
Are my priorities aligned with where design creates most enterprise value?
Have I found the right balance between vision setting and execution oversight?
Am I maintaining sufficient bandwidth for future-focused thinking and innovation?
Have I redefined what "craft mastery" means for my own role in an AI era?

Leadership Model

Am I effectively balancing creative leadership with business acumen?
Have I built strong relationships with key stakeholders across the organization?
Am I role-modeling the design thinking and innovation mindset we need?
Have I evolved my leadership style to drive enterprise transformation?
Do I demonstrate comfort with ambiguity and rapid change?

Growth & Development

Am I continuously expanding my strategic and business leadership capabilities?
Have I built a strong network of peers and mentors for perspective and growth?
Am I effectively developing the next generation of design leaders?
Am I developing the business and strategic acumen our future requires?
Do I have effective mechanisms for continuous learning and adaptation?

Personal Impact

Have I positioned myself as a strategic leader beyond design?
Am I influencing at the right level of the organization?
Do I have the right metrics for my own effectiveness?
Am I creating space for others to grow into strategic roles?

Implementation Guide

The value of these questions lies not in their occasional review but in their systematic application to design leadership practice. Here's how to use them effectively:

Regular Self-Assessment

Design leadership requires ongoing reflection and adjustment. Schedule quarterly deep-dives into these questions, ideally coinciding with your organization's planning and review cycles. Block focused time — at least two hours — to honestly assess your answers and their implications.

During these reviews, look for patterns rather than just individual answers. Which areas consistently need attention? Where do you see the same challenges recurring? These patterns often reveal systemic issues that require structural solutions rather than tactical fixes.

Document your reflections and revisit them over time. This creates a valuable record of your strategic thinking and helps identify both progress and persistent challenges. Pay particular attention to areas where your assessment has shifted significantly — these often indicate important changes in your organization's context or needs.

Team Development

These questions serve as powerful tools for developing your broader design leadership team. Use them to structure development conversations and guide capability building across your organization.

In one-on-one sessions with direct reports, select relevant questions to explore together. This helps senior design leaders understand how their work connects to larger strategic objectives. It also provides a framework for discussing their growth and development needs.

For team sessions, choose specific sections that align with current challenges or opportunities. For example, use the Innovation Excellence questions to guide a leadership offsite focused on scaling innovation practices, or explore the Organizational Alignment section when working on design systems strategy.

The questions can also help identify gaps in your team's collective capabilities. Where do you see hesitation or uncertainty in the answers? These areas often highlight the need for targeted development or new expertise.

Strategic Planning

Embed these questions into your formal planning processes. They help bridge the gap between high-level strategy and practical execution by forcing consideration of key enablers and dependencies.

During annual planning, use them to test the completeness of your strategic thinking. Do your plans adequately address each dimension? Have you accounted for the organizational capabilities needed to execute successfully?

In quarterly reviews, select relevant questions to structure the discussion. This helps maintain focus on strategic issues rather than getting lost in tactical details. It also provides consistency in how you evaluate progress and make adjustments.

Share appropriate questions with cross-functional partners to guide strategic discussions. This helps establish shared language and frameworks for thinking about design's role in driving business value.

Success Indicators

While the questions themselves are qualitative, look for quantitative indicators that show progress in each area:

Strategic Impact
- Design representation in key decision forums
- Business metrics influenced by design initiatives
- Executive stakeholder engagement scores
Operational Excellence
- Design system adoption rates
- Speed to market improvements
- Quality metrics across the portfolios
Team Performance
- Leadership pipeline strength
- Team engagement scores
- Retention of key talent
Innovation Outcomes
- Success rate of new initiatives
- User adoption of new features
- Revenue from design-led innovation

Moving Forward

The role of design leadership continues to expand and evolve. These questions provide a framework for navigating this evolution with intention and strategic clarity. They help design executives maintain focus on what matters most: building teams that can execute with a high bar, creating systems that enable scale, and driving innovation that delivers lasting value.

Use these questions not as a checklist to complete, but as prompts for deeper strategic thinking. Let them guide regular reflection on your organization's direction and capabilities. Share them with your leadership team to spark meaningful dialogue about priorities and possibilities. Most importantly, adapt them to your specific context and challenges.

Remember that the goal isn't perfect answers but better questions — ones that promote strategic thinking, reveal hidden opportunities, and drive meaningful progress in building design's influence and impact across the organization.

The future of design leadership will be defined by those who can consistently connect creative excellence with business impact, while building the organizational capabilities needed for sustained success. These questions can help light the way forward.

September 5, 2023

Rachel Kobetz Joins PayPal as Chief Design Officer

Former Global Head of Design at Expedia Group brings extensive design vision, experience strategy, and operational leadership to PayPal

PayPal today announced that Rachel Kobetz has joined the company as Senior Vice President and Chief Design Officer (CDO), reporting to John Kim, Executive Vice President and Chief Product Officer. Rachel joins PayPal following more than 20 years in senior leadership roles building design organizations at some of the world’s largest companies.

Rachel comes to PayPal from her most recent position as SVP and Global Head of Design at Expedia Group, where she was responsible for leading the company’s Experience Design organization. Her responsibilities included design vision, experience strategy, and operational leadership for products and services for all Expedia Group stakeholders, including employees, travelers, partners, agents, and developers. Prior to this, Rachel was SVP and Head of Experience Design at Bank of America where she led the Experience Design organization to drive the end-to-end transformation of core product and service experiences. Rachel was also the Head of Studio, New Product UX at Amazon’s Design Group, and prior to this was Senior Director of UX at Samsung’s Mobile Innovation Lab.  

In her role as PayPal’s SVP and CDO, she will be responsible for the design strategy and execution at scale across all end-to-end experiences (including PayPal, PayPal Braintree, Happy Returns, Honey, Venmo, Xoom, and Zettle) for consumers, merchants, developers, and employees globally.

“Rachel has a standard of excellence, creativity and innovation that we are excited to leverage during PayPal’s next phase,” said John Kim, EVP and CPO. “Her experience in financial services and consumer tech coupled with her ability to make technology more human makes her the perfect choice to help us create our next generation of experience-led products and services.”

“We have a massive opportunity to evolve our products and deliver ground-breaking design,” said Rachel, incoming SVP and CDO at PayPal. “I bring a renewed focus on design strategy, craft, quality, and innovation. And with other leaders throughout the company, we can elevate our experiences to set the bar within and across industries.”

August 20, 2022

The People Who Have Influenced My Design Practice and Leadership

Throughout my career, I’ve been influenced and inspired by many people, books, and experiences that have shaped my approach to the work. But there are a few who’s philosophy and perspectives have become part of my designer DNA and ethos.

By internalizing their teachings and perspective and evolving from them, I can attribute the foundation of my design practice and leadership to these influential people, who continue to inspire me and constantly renew my passion for design:

Charles and Ray Eames

“The details are not the details. They make the product.”

Not only were Ray and Charles an amazing couple well known for their modern furniture design, they pioneered work in film, environments, textiles, and architecture, and pushed the boundaries of what design means and could be. Their bar for quality and attention to detail are why I exude the mantra that the details are what separates good from great.

When asked by Madame L’Amic, curator of the exhibition “Qu’est ce que le design? (What is Design?)” at the Musée des Arts Décoratifs, Palais de Louvre in 1972, Charles Eames responds:

Q: “What are the boundaries of Design?”
A: “What are the boundaries of problems?”

Bruce Mau

“Design is the ability to imagine a future and systematically execute that vision. So if you think about what all designers do, they’re all futurists. They’re all thinking about what’s going to happen. They’re going to make something new happen in the world. They’re all trying to make the world a better place. I’ve yet to meet a designer who wakes up in the morning thinking, “I think we could do something worse.” That’s not our mandate. That ability to create a vision is one of the most powerful tools that a designer has. We don’t really understand how powerful it is — it’s an incredible power to create the future by showing somebody what it looks like.”

If you haven’t read Massive Change and MA24 — do it.

Dieter Rams

Dieter is a goldmine of quotes and inspiration, especially his ten principles for good design. Modern, minimal, and timeless, his “as little design as possible” philosophy always has me pushing teams to find the elegance in a solution, paring it back to its essence. Distill complexity, expose simplicity. But I find his approach to life and expectations for designers even more intriguing.

“Good designers must always be avant-gardists, always one step ahead of the times. They should — and must — question everything generally thought to be obvious. They must have an intuition for people’s changing attitudes. For the reality in which they live, for their dreams, their desires, their worries, their needs, their living habits.They must also be able to assess realistically the opportunities and bounds of technology.”

Brigitte Borja de Mozota

“Design is a management tool that creates differentiation in the internal capabilities of the company. Design is no longer seen as the output of design-form, but as a creative and management process that can be integrated into other organization processes, such as idea management, innovation management, and research and development management, and that modifies the traditional structure of process management in a company.”

Brigitte is a researcher in management science, and wrote one of the first books I read on Design Management, which became my handbook. Her work on The Four Powers of Design clearly outlines a balanced scorecard approach to measuring and communicating Design’s impact.

These leaders have shaped my design leadership approach, my practice, and inspired me to shape the world around me. I hope by sharing this it will move others to learn more about them and become inspired themselves.

June 12, 2022

10 Truths From Building Design Organizations at Scale

Observations from a chief design executive that apply across industries and companies.

Having the opportunity to build design orgs in some of the largest companies in the world, I’ve observed that even with completely different cultures, org structures, and industries…some things stay the same.

You will never have enough designers. You will never have enough time. You will always be building the plane while it’s flying. Design is a valuable, scarce resource. The sooner you navigate this truth and use it to your advantage, the sooner you build leverage.
Design transformation is company transformation. The work you’re doing isn’t just for the design org. Becoming an experience-led company transforms the culture. Realize that change management is your job.
Chart tomorrow’s vision while building for today. North stars are in the ether if you’re not improving current experiences. Drive impact in the short-, medium-, and long-term. Short-term wins become proof points that build reputation and provide runway. The medium-term is where the magic happens.
Show up as a company leader, not just a functional leader. Design cuts across orgs and teams, which provides a unique view of the environment. When you make that mindset switch, you’ll get pulled into the conversations and decision making you wanted all along.
Always be recruiting. The coffee chat you have today might be a future hire five years from now. You are responsible for treating your talent pipeline like a supply chain, always keep it moving.
Your “first team” is your boss and peers, not your directs. If you only focus down, you’ll realize you’ve been neglecting across and up. That’s where important communication, relationships, and visibility is required for the success of your organization.
Be the matchmaker. Connecting the dots across the company will unearth teams that don’t talk to each other, duplicative efforts, and opportunity areas. Build the network, streamline the work, and unearth new business models.
Trust is the foundation of all great teams. Take the time to build trust with your team, throughout your org, with your peers, and your manager. Take a 360 degree approach, and be the constant gardener.
No one understands what you do, so explain it to them. Don’t leave the design process in an opaque box that produces magic. The more people understand the complexity and rigor behind the work, the more others will respect and champion Design.
As you scale, the talent you hire and the mechanisms/levers you create will determine how your culture evolves. Make sure you’re minding the shop and sharing artifacts that guide decision making and incentivize desired behaviors.

May 15, 2022

Mastering Orchestration: 8 Ways to Drive Business Outcomes as a Design Leader

Connecting competitive advantage and value to customer and business impact.

As a Chief Design Officer (SVP/VP Design, Head of Design, etc.), you’re responsible for connecting the value and competitive advantage that design creates to customer and business impact. Here are eight ways to drive business outcomes no matter what scale you’re operating.

Decode corporate strategy and connect the threads. Translate the corporate mission, vision, and strategic intent into the differentiating design capabilities that will provide competitive advantage. Develop a clear thread that ties the strategies together — from corporate strategy all the way down through to experience strategy. Illuminate the alignment and connection. Translate corporate objectives into design objectives.
Define an inspiring design vision and clear execution path. Create the design vision, and the three-year strategic plan, principles, roadmap, and operating plan to get there. Define goals that lead to the clear outcomes and milestones defined in the strategic plan. Develop an inspiring vision of the future. Make strategy tangible through narrative and prototypes. Socialize, get feedback, and communicate far and wide.
Drive a dual operating system. Deliver for today while making strategic investments in the future. Orient towards experience maps and roadmaps that paint a clear North Star and define the progress signposts on the way there. Make sure you’re executing short-term responsibilities while also shaping the future. Align your best talent to the most critical work for the company, while making space for exploration to go after what’s next.
Identify beacon programs. Use beacons as the light that guides the organization to new ways of working. These become your case studies and examples of how being experience-led yields better outcomes. Leverage these programs as catalysts to embed human-centered design into the fabric of the organization.
Make teaming a priority and build organizational leadership muscle. The larger and more matrixed the company, the more important this will become. This is a requirement if you want to reinvent any experience at scale. Teaming across the organization will pull together diverse, cross-functional perspectives, forge strong working relationships, increase collaboration, and accelerate the work needed to achieve the business outcomes you’ve defined.
Create quality and coherence mechanisms. Leverage orchestration and governance to create experience cohesion. There’s an interesting dichotomy that happens as you elevate as a leader and your organization scales. You can no longer be close to every program, and yet, you need to be able to hold the quality bar and ensure cohesion.
Show don’t tell. Measure what matters, and align to shared outcomes and metrics wherever possible. Define leading and lagging metrics for all of your priorities/objectives. Benchmark current state and get moving.
Connect design outcomes to customer and business impact. As a [design] leader, there’s a critical difference between stating and demonstrating business impact. How you measure progress and the effectiveness of your plan is where the rubber meets the road. Develop a scorecard, impact reports, narrative artifacts, and ongoing communication. Continuously communicate progress across and up.