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Leading Design Through the AI Shift. A progress report.
5/1/26
Five months in, here's what I'm seeing leading my design org through the AI shift.
The work needs room — to build, to break, to ship. No permission slips. No central gatekeeping. Just the conditions for play, with real product surfaces underneath. That's the call I made early, and it's the one I'd make again.
What came out of it, in half a year (aside from the work going out to into the world)
In a single month, four members of the team shipped four strategic vision prototypes — using a combination of Higgsfield, Replit, Google Vids, ChatGPT, Adobe Podcast, Nano Banana, and Claude. Higher production value than anything we'd shipped before. Faster than anything we'd shipped before. The output wasn't just better. It was a different category of artifact entirely.
One thing to be clear about: the ceiling of what AI produces is set by the ceiling of the people using it. That work was done by principal- and senior-level designers, with content design and research guiding alongside, and strong product management partnering throughout to unblock decisions and protect the timeline. AI didn't make the work great. They did, and AI gave them new range. This isn't a click-and-magic situation — it's a multi-disciplinary one.
That month also didn't happen because the tools were good. It happened because the structure around the tools was good — clear decision-making, fast unblocking, and protected space for creativity to compound across people instead of stalling on approvals. The AI was the accelerant. The talent was the engine. The partnership and leadership were the fuel.
Beyond that month, the team has built roughly thirty distinct AI tools and frameworks since the start of the year — across five categories that, taken together, look more like an operating system than a tool list. Two strategic frameworks change how the org makes decisions. The rest are split across internal productivity, product experience surfaces, admin efficiency, and storytelling.
The two strategic frameworks are the ones I'd want any leader at my altitude to notice. With a peer, I co-authored a Design Support Hub and AI Collaboration Model — a framework, a Replit app, and a live operating ritual run weekly by a principal designer on the team — that unblocks self-serve capacity for design-adjacent partners through guided standards while de-risking the quality of self-served outputs. Intended to influence the operating reference for our entire design org. With our content design leader, I co-authored an Experience Health framework, currently piloting into Weekly Business Reviews — the first attempt my function has made to connect design quality to true business outcomes in a structured, repeatable way. I'm watching closely to see how it all lands but the excitment is there.
A Chief of Staff dashboard I built for myself, with persona-grounded streaming AI and live integrations, is now traveling — other leaders are picking up the ideas and shaping it to their own contexts. What I'm seeing in that is more interesting than the dashboard itself: dashboards are utilitarian at their core, and their job is to help the user take the next best action. The only way they do that well is by being deeply personalized. The shape changes with the role, the operating style, the priorities. The future of this ecosystem isn't one tool serving everyone. It's a substrate that bends to the person using it. That's a different design problem than we've solved at this scale before, and it's the one I think about most.
5 months in. Feels like we just got started.
Tools are good, and getting better. But more importantly, the leadership work around the tools is what makes them compound.
The tools will keep improving regardless of what any of us do. What doesn't happen automatically is the structure underneath — the decision-making, the unblocking, the protected creative space, the sensitivity to where each person is on their own curve, the willingness to credit forward and let the team teach each other. Without that, the tools get faster, but the work doesn't get better. With it, the tools become an accelerant on something real.
That's the work I think most about right now. Three things in particular:
1. AI delivers real speed — and the speed of synthesis and remixed exploration in particular is elite. But the work to get something to a production-grade standard still requires rigor, and the quality of the remix is bounded by the creativity of the user.
The synthesis gain is the strongest. Pulling research, prior art, market context, pattern analysis, and frame-setting together — the cognitive heavy lift that used to take days — now happens in hours. That's not a small improvement. It's a different category of capability.
The speed of remixed exploration is also elite. Testing variations, pushing directions, iterating on a frame until the right one surfaces — the loop that used to span sprints can now span hours. But the quality of what comes out of that loop is directly tied to the creative range of the person driving it. A designer with sharp taste and strong instincts produces a fundamentally different remix than someone treating AI as a slot machine. The tool doesn't lower the creativity bar. It raises the leverage of whatever creativity the user brings.
The first-draft gain is real, too. AI compresses ideation and rough production into a fraction of what they used to take. I've watched my team do in days what would have taken weeks.
But getting from a synthesized, well-explored first draft to something that meets the bar for production — taste, edge cases, accessibility, edge-of-system behavior, the things that make experience feel intentional rather than generated — still takes time. Rigor takes time. Quality takes time. That part hasn't compressed in the same way, at least not yet. It will. Just not yet.
For non-practitioners — PMs, engineers, leaders sketching ideas — synthesis and first-draft speed is the whole story, because a fast, well-framed first draft is more than they had before. That's net new capacity, and it's genuinely valuable.
For design practitioners, the picture has more layers. Synthesis is faster. Remixed exploration is faster. First drafts are faster. And the creativity required to make the remix good is still entirely human. The hours redistribute — less time pixel-pushing, more time directing. Less time on rough exploration, more time on prompt engineering, taste calibration, edge-case curation, and quality review.
That isn't a failure. It's the actual transition right now. The honest framing: AI lowers the floor for non-practitioners. It raises the ceiling for practitioners — but only in proportion to the creativity they bring to the prompt. Synthesis and remix are the elite gains. Systematic production rigor is the remaining work. Conflating these sets the wrong expectation for designers, for leaders, and for the execs writing the headcount plans.
2. The tooling landscape is fragmented, personal, and constantly merging. There is no single fluency to acquire.
Every designer on the team has a different stack. The capabilities overlap, then merge, then diverge again. A tool that was best-in-class six weeks ago is mid-tier today. A tool that didn't exist six weeks ago is now central to how someone works.
That fragmentation has a real cost we don't talk about enough. There's a constant background load on every practitioner — evaluating new tools, re-learning workflows, swapping muscle memory, deciding what to ignore. The pressure isn't just "get fluent." It's "stay fluent against a target that won't sit still." That's not a complaint, it's the actual job description right now.
The leaders who'll handle this well stop chasing one-tool-to-rule-them-all and start investing in what's actually durable: taste, judgment, the ability to direct outputs, and the resilience to keep learning when the floor moves. You cannot automate curiosity.
3. The human work isn't soft. It's the structural prerequisite for everything else — and trust is the architecture.
The pace of change is real. The cognitive load is real. The pressure to stay fluent against a moving target is real. None of that is sustainable if the people doing the work aren't held alongside it.
We do weekly team reflection together. Not a status meeting. Not a retro on what shipped. A check-in on how we're metabolizing the change — what's exciting, what's heavy, what's making people second-guess themselves, what they need from each other and from me. We talk about which tools are landing and which ones are creating friction. Where the work feels generative and where it feels performative. What's worth letting go of. What new instincts are forming. The conversation shifts every week because the ground does.
It's therapeutic, and it's also necessary. The rate of change in this work outruns any individual's ability to process it alone. The antidote is doing it together — which means leaders have to make space for it, not just permit it. A check-in that's optional gets skipped. A check-in that's structural gets metabolized.
The other half of the architecture is trust. My team knowing I trust them — to try things, to break things, to pick the tools that fit how they think, to disagree with me, to bring the work forward in their own voice — is paramount. Not aspirational. Paramount. The autonomy at the start of this post doesn't work without it. The thirty tools and frameworks don't get built without it. The strategic vision prototypes don't ship in days without it.
Trust is hard to talk about in a leadership post because it may sound soft. It isn't. In a moment of constant change — when nobody knows what tool will be best in six weeks or what the work will look like in a year — trust is the only thing that lets people move at speed without breaking. It's not a perk. It's load-bearing infrastructure.
The environment I keep talking about is, in the end, just a structure for trust to live in.
Five months in, the work is environmental — and ongoing. Make it safe to try. Make it cheap to fail. Make it visible when it works. Scale what works without forcing it on people who aren't ready, inspiration within proximity of curious high adopters is the better tactic.
Speed at this scale isn't free. It requires definition & structure around decision-making, unblocking, and creative permission. It requires multi-disciplinary talent at the table — design, content, research, product — moving together. AI compounds creativity only when the leadership scaffolding lets people move and the partnership underneath is real. Without that, the tools just create faster versions of the same bottlenecks.
Execution is cheap. Ideas are everything. Taste is the constraint. And the environment is what makes all three possible.
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10/25/24
My time at Zillow thus far has been an extraordinary journey of reimagining how we help people find their way home - not just as a transaction, but as a profound part of the human experience.
In a world where technology touches every aspect of our lives, few products have the privilege of remaining relevant throughout one's entire life journey. Home is one of those rare constants - a thread that weaves through every chapter of our story, from first apartments to family homes and beyond.
Leading design teams through this landscape isn't just about solving complex problems; it's about embracing the remarkable opportunity to transform one of life's most meaningful and consequential experiences. As we build towards our 'golden era’ of design,' as our CDO Jenny Arden often mentions, we're not just redefining workflows - we're crafting moments of joy, relief, and possibility in people's lives. We're fundamentally rethinking how technology can make the dream of home more achievable for millions, transforming intricate, tiresome real estate processes into intuitive, meaningful experiences within our super app aspiration.
Staying grounded in my leadership philosophy which centers on nurturing innovation while guiding teams through transformative change, always remembering the profound trust people place in us during their housing journeys. By fostering a culture of continuous learning and unwavering quality, we're building an environment where designers feel empowered to push boundaries and reimagine what's possible. This delicate balance of ambitious innovation and human-centered execution isn't just about building products - it's about opening doors to new possibilities in people's lives, getting home.
This past year I’ve been constantly inspired by my peers who fearlessly push me to tackle this complexity with creativity and determination to be better every day.
The future holds endless possibilities for how we can transform this paradigm and be a true leader not only in the real estate, but in design at large and I can't wait to see what we'll achieve in the year to come.
Stay tuned.