DX Perspective: Design For The AI Age, Intentional Org Design, and The Art of Not Knowing
Hi all!
Here’s your weekly dose of DX Perspective, a list of what I’m exploring and thinking about. Feel free to forward this along to friends.
kw picks
This understanding of interfaces has shaped my perspective on design throughout my career, leading me to see design as largely deterministic. I could visualize how interactions would work. The sequence when a user clicks a button, how information appears, how it adapts to different screens. It's dynamic, but predictable. I could visualize the user's journey and think about how to improve it. That changes with AI and LLMs.
VII. What makes an artefact, artefactful? – Studio D
Think about something you worked on for a decent length of time that you shared with the world. What happened next? Of the audience members you targeted, who engaged with it, shared it with their community? Alternatively, who pushed back on it, or ignored it completely?
TBM 350: Connecting Dots by John Cutler
I'm obsessed with the mess of product development. Over the last couple of weeks, I've spent a lot of time with operations leaders trying to bring some order to that mess.
What I'm reading
How to Intentionally Design Your Org, From Square’s Former CEO
Former Square CEO, AWS's first GM and 12-year Microsoft veteran, Alyssa Henry, walks us through the two crucial considerations for organizational design — your business and your people — and how to connect them.
Design at MANUAL - by Tom Scott and Filippos Protogeridis
I am excited to tell the story behind the design team at MANUAL. Healthcare is an industry where design is needed more than ever and after a recent discussion with Filippos Protogeridis about how he’s building the design team at MANUAL I wanted to record our conversations and share with the community more of behind the scenes.
The Theater of Leadership Development
Something is about to unfold. Not on a stage, but in a mirror. Seven acts. A lens, slowly turned. Not a manifesto. Not a toolkit. A philosophical unmasking of the leadership industry—its myths, its performances, its polished evasions.
The Evolution of Interfaces from Option-Based to Goal-Based by Aishwarya Sreenivas
Where do we need to rethink UI elements from first principles in the Age of AI?
The Art of Not Knowing: A Zen Approach to Strategic Foresight Shoshin – beginner’s mind – is the Japanese Zen concept that opens doors that expertise over time slams shut. In Zen monasteries, monks sweep every day as if for the first time – the task isn’t about being the best or the fastest but about encountering every fallen leaf, every bit of dirt with a fresh mind.
38 Web strategy & design articles tagged Ai Design – Luke Wroblewski
Emerging Tech
AI Agents Using MCP = Your “Guy in the Chair”
In 1982, at the heart of the Tron universe was the MCP, or Master Control Program. It was an old-fashioned mental-model of a computing system.
Tobi Lutke, Shopify CEO on AI.
"I heard this internal memo of mine is being leaked right now, so here it is.”
Tools and Resources
My recent articles
Are You Actually Making Progress? How I Rewired My Weekly Reflection to Drive Real Impact
Strategic Design Leadership: Essential Questions for Design Executives
Fueling Innovation: How Design Leaders Drive Product Transformation
Moving Beyond Execution — The Evolution to Strategic Design Leadership
Decoding The Future: The Evolution Of Intelligent Interfaces
🔈 Design Leadership at Scale — Shape The Future of Business
DLS courses are built for design leaders ready to sharpen their strategy, expand their influence, and lead at the highest level. Whether you‘re mapping your next career move, strengthening design operations, or stepping into executive leadership, these programs give you the frameworks and insights to drive real impact.
DLS: Career Strategy (May 17—18)
Your career journey deserves intention and strategy. This weekend immersive is designed for design leaders who are ready to map out their path, elevate their impact, and align their leadership trajectory with long-term goals. Whether refining your current role or preparing for new opportunities, you’ll gain actionable frameworks to craft a career that stands out in a competitive market.
DLS: Executive (June 23–July 3)
This advanced course is tailored for senior design leaders—Senior Directors, VPs, SVPs, and CDOs — who are ready to lead at the intersection of design, business strategy, and emerging technology. Dive deep into aligning design with business objectives, fostering product culture transformation, and building scalable operations that support innovation and growth.
DLS: Operations
Scaling a design organization without compromising quality or culture is a challenge every design leader faces. This course equips senior and emerging design operations leaders with the tools to build robust infrastructure, optimize processes, and drive operational excellence. From talent development to systems that support rapid growth, this program is crafted for leaders ready to take their teams to the next level.
DLS: Director+
Built for experienced design leaders ready to step up to executive roles, Director+ focuses on leading in complex, matrixed organizations, scaling your influence, and making high-impact decisions. This course will empower you to lead with clarity and confidence, bridging design with broader business goals to drive value across the organization.
And please give me feedback. Which bullet above is your favorite? What do you want more or less of? Other suggestions? Please let me know.
Have a great weekend.
— Rachel