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.

May 22, 2023

Decoding The Future: The Evolution Of Intelligent Interfaces

A futuristic smart city during the day, with skyscrapers, greenery, and a large rectangle pool of water reflecting the buildings and the sky
kobewan x Midjourney 2023

In the tech world, there's always a 'next big thing' on the horizon. Right now, that horizon is dominated by conversations about artificial intelligence, mainly ChatGPT, Google’s Bard, and Generative AI tools like Midjourney and Dall-E 2. Some professions are embracing Generative AI, while others are fearing it.

Included in that conversation is a lot of talk about chatbots. But chatbots are not the future, they are our present. In many ways, chat interfaces are the foundation of more conversational and natural interactions with systems and computers, but really they are the start of something much bigger.

We’ve been anticipating this future for a while, but it hasn’t really been possible until the last couple of years when the right ingredients and technology have converged. It’s an exciting time.

Ubiquitous Computing and Intelligent Interfaces

What happens when we move beyond our screens and unleash computing power, the internet, and AI into the real world? It starts to get interesting. Welcome to the age of ubiquitous computing — the future of intelligent systems.

Ubiquitous computing, also known as pervasive computing or ambient intelligence, is a concept first proposed by Mark Weiser, Chief Technologist at Xerox PARC, in the late 1980s. Weiser later wrote a paper on the topic in 1991 titled "The computer for the 21st century". The idea behind ubiquitous computing was to create an environment where computers were embedded seamlessly into the physical world and where human-computer interaction was natural and effortless. Where we forget about the underlying technology. Weiser envisioned a world where computing would be "invisible," and users would be surrounded by an "information fabric" that would provide them with relevant information and services.

Ubiquitous computing has been somewhat realized in the Internet of Things (IoT), the network of interconnected devices and sensors embedded in everyday objects, from smart homes to self-driving cars. But, the original vision of ubiquitous computing as a truly seamless and integrated experience has yet to be fully realized.

Then there are intelligent Interfaces, representing a paradigm shift in human-computer interaction. Unlike traditional GUIs (Graphical User Interfaces) that require users to learn the system's language, intelligent interfaces aim to make the system understand the user's language. Instead of humans adapting to the system, the system adapts to them. Intelligent interfaces leverage human instincts and behaviors to create a more intuitive experience. These systems integrate artificial intelligence (AI) and can leverage everything from touch interfaces, voice recognition systems, and gesture-based controls to brain-computer interfaces — they’re multi-modal.

These intelligent systems can make our interactions with technology more intuitive, natural, and efficient. Think Siri, but on steroids. So as we stand on the brink of a new era in human-computer interaction, it's worth exploring how these interfaces have evolved, where they're headed, and how they will revolutionize how we interact with devices and the world around us.

“The future is already here — it's just not evenly distributed.” 
— William Gibson

Current State

The journey has been gradual, with momentum building in the last five years. It started with command-line interfaces, moved to graphical user interfaces, and then to touch interfaces with the advent of smartphones and tablets.

A spectrum that illustrates the evolution from interfaces that are built around computers to interfaces built around humans, from punchcards, keyboards, and mice to touch, voice, gesture, and gaze.
Slide from my Leading Innovation presentation, 2019

Today, we're already seeing the beginnings of intelligent interfaces. Technology is getting smarter, from Alexa managing our smart homes to AI algorithms recommending our next Netflix binge. They're in our phones, our cars, even our refrigerators. And they're changing the way we interact with technology. We’re now using much more natural and multimodal interaction in everyday objects. We're seeing the rise of voice interfaces like Apple's Siri and Google Assistant, gesture-based controls in gaming systems like the Nintendo Switch, and even early versions of brain-computer interfaces (BCIs) from companies like Neuralink.

As consumers, we’ve become accustomed to using biometrics, like facial recognition and fingerprints, to authenticate and unlock our devices. Even BMW is starting to use gestural interaction and gaze for hands-free interaction in their cars. Augmented Reality (AR) and Virtual Reality (VR) interfaces are becoming more popular, providing immersive experiences that blend the virtual and real worlds. This is seen in devices like the Meta Quest and Microsoft HoloLens.

Interaction patterns of the future.

The chat interfaces we’re seeing today with ChatGPT and others are setting the foundation for multimodal systems of the future. The back-and-forth interaction volley will lay the groundwork for how systems interact with us, anticipating our needs, confirming our requests, and acting on our behalf.

We’ve seen glimpses of ubiquitous computing and intelligent interfaces in TV shows and movies, but it’s always seemed to be further into the distance. However, we’re now on the cusp of an explosion of product innovation that advances in AI, computing, and hardware will finally enable. It’s exciting that what used to be science fiction and innovation concepts are now becoming reality. Movies and TV shows have played a large part in inspiring us to push further.

Minority Report (2002)

One of the most famous examples is the user interface in Minority Report. The movie has been highly influential in shaping public perceptions of interfaces and has inspired real-world applications of gesture-based interfaces and other emerging technologies. Most remember the gestural interface used by Tom Cruise’s character, what’s not widely known is the computer system used in the movie. John Underkoffler of Oblong Industries created the g-speak Spatial Operating Environment, which uses natural gestures — no keyboard, mouse, or command line. Underkoffler also worked on the gestural holographic interfaces in Iron Man (2006).

Her (2013)

The gesture-based interfaces in Minority Report and Iron Man gave us a glimpse of what's possible, while the voice interface in the movie Her showed us a future where our devices understand us on a deeply personal level. Her explores the idea of natural UI, the potential for human-like interactions with digital assistants, and the potential implications of a future where technology becomes more integrated into our personal lives.

Maeve’s “Attribute Matrix”, Westworld

Another great example is Westworld, which explores the concept of ephemeral interfaces and artificial intelligence, where android hosts adapt and respond to the guests' actions and preferences in real-time, creating a highly personalized and immersive experience in a technologically advanced amusement park. It gets even more interesting when the androids return to the “real world.”

Blade Runner 2049 (2017)

Blade Runner 2049 offers a glimpse into a future where projection mapping and augmented reality create immersive and dynamic environments. In the movie, projection mapping creates large-scale holographic displays that interact with the physical environment, creating an immersive and surreal atmosphere.

Iron Man’s J.A.R.V.I.S. AI assistant and the virtual assistant FRIDAY in Captain America: Civil War are great examples of natural UI. These interfaces demonstrate the potential for natural language processing and machine learning to create sophisticated and responsive digital assistants to help us navigate our increasingly complex and interconnected world.

Intelligent Interfaces promise to make our interactions with technology more natural and effortless. By leveraging our behaviors and instincts, they can also reduce the learning curve associated with new technologies, making them more accessible to a broader range of users.

Emerging technology shaping the future

The interface of the future is not chat — it’s multimodal and ubiquitous.

The future is not pages and pages of UI flows or detecting whether you’re on desktop or mobile. Our future interfaces will be intelligent, contextual, and ephemeral. Just enough interface compiled in real-time, based on context and relevance.

UI that appears when it’s needed and hidden when it’s not.

The ability to interact by voice, touch, or typing, easily switching modalities based on what’s natural for the user. Where interfaces are fluid, and sound and haptics enhance calm, ambient interactions. A proactive concierge that provides what’s needed based on understanding who you are and gets better the more you interact with it.

Systems that adapt to humans instead of the other way around.

Imran Chaudhri, Co-Founder, Chairman, and President of Humane at TED 2023

Some companies are already working towards this vision of the future. At this year’s TED Conference, Humane’s Imran Chaudhri provided a preview of their unreleased tech, a system where AI, computer vision, and projection come together to create an assistant that’s with you throughout your day without using a phone — where the device disappears. Early views of this type of system are reminiscent of Pranav Mistry’s 2009 SixSense demo at TEDIndia of a wearable gestural interface, his MIT Media Lab thesis project. Pattie Maes, who runs the Media Lab's Fluid Interfaces research group, created a huge buzz at the TED main stage that year, introducing the project.

Mercury OS

Another team pushing the boundaries, former Apple designer and founder Jason Yuan and Sam Whitmore, have just received funding for new.computer, whose mission is to “create a future where computers intuitively adapt to humans, forging relationships as essential as the tools we use today.” Jason Yuan’s name may be familiar for creating Mercury OS, a minimal, fluid reimagining of the traditional operating system focused on the user’s intention instead of apps and folders.

Refik Anadol, Machine Memoirs

And some of the most experimental art may push the boundaries and help shape how we interact with future systems. Refik Anadol uses projection mapping and machine learning to create immersive AI data sculptures and interactive art installations. Anadol's work blurs the line between the physical and digital worlds, creating beautiful and thought-provoking environments.

Advancements in AI, machine learning, natural language processing, and human-computer interaction will likely drive the evolution of intelligent interfaces over the next decade. As we think about the types of new interactions and experiences that will evolve, here are some of the trends and developments that will influence that future:

  1. Multimodal Interfaces: Future interfaces will likely combine text, voice, visual, and even tactile inputs and outputs. This will allow users to interact with AI in whatever way is convenient or intuitive for them at any given moment. For example, you might speak a command to your AI assistant, then receive a visual response on your smart glasses.
  2. Context-Aware Interfaces: AI will become better at understanding the context of user interactions. This means that the AI will understand what you're saying, where you are, what you're doing, and what you might need in that specific situation. This could involve integrating data from various sensors and sources to provide more relevant and personalized responses.
  3. Emotionally Intelligent Interfaces: AI will become more adept at recognizing and responding to human emotions. This could involve analyzing voice tones, facial expressions, or even physiological signals to understand the user's emotional state and adjust its responses accordingly.
  4. Proactive Interfaces: Instead of waiting for commands, AI interfaces will become more proactive, anticipating user needs based on patterns, habits, and preferences. For example, your AI assistant might suggest leaving early for a meeting if it knows there's heavy traffic on your usual route.
  5. Immersive Interfaces: With advancements in AR, VR, and projection mapping technologies like those demonstrated by Humane, we can expect more immersive AI interfaces. These technologies could allow for more natural and intuitive interactions with digital content.
  6. Collaborative Interfaces: AI will become more capable of collaborative problem-solving, working alongside humans to tackle complex tasks. This will involve understanding and contributing to human-like conversations, including recognizing when to take initiative and when to ask for clarification.

In the future, we can expect more personalized and immersive interfaces. AI and machine learning will continue to make interfaces smarter and more adaptive. They'll learn from our habits and preferences, making our interactions with technology more efficient and enjoyable. AR and VR will continue to evolve, creating more immersive and interactive experiences, blurring the lines between the physical and digital worlds, and creating new possibilities for interaction. Though still in their infancy, Brain-Computer Interfaces (BCIs) hold the promise of a future where we can interact with technology using our thoughts alone.

We'll see a move towards more continuous, personalized, ambient interfaces. These interfaces will be seamlessly integrated into our daily lives, allowing us to interact with AI in a more natural and intuitive way, similar to how we interact with other humans. Consider a combination of voice, gesture, gaze, and even thought-based interfaces in the future enabled by technological advancements like BCIs.

The latest research in the field is fascinating. Scientists are exploring everything from AI algorithms to brain-computer interfaces, and their findings could revolutionize how we interact with technology. Researchers at MIT's Computer Science and Artificial Intelligence Laboratory (CSAIL) are developing systems that can understand and respond to human emotions, potentially making our interactions with technology more empathetic and engaging. Meanwhile, researchers at the University of California, San Francisco, are making strides in BCI technology, recently developing a system that can translate brain signals into complete sentences.

Intelligent Interfaces represent the next frontier in human-computer interaction. They hold the promise of making our interactions with technology more natural, intuitive, and engaging. While significant challenges and ethical considerationsexist, the potential benefits are immense. One thing is clear — how we interact with technology is about to change significantly.


This is a more dense approach than my usual posts. As always, send me your feedback. If the community is very interested in this topic, I’ll write part two, where I’ll dive into intelligent interfaces' challenges, ethical considerations, and how the role of designers will evolve. I’ve been trying out ChatGPT as my research assistant, how did it do?

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