The Work Always Wins
An essay by Austin Knight
Summary
It's easy to get stuck when pushing for something new. Process and PRDs, feedback and debates, alignment chasing. Ironically, process can stall progress. When it does, it's a sign of misplaced focus. A call to get out of docs and get back into design. Real momentum comes from real work: functional prototypes that are tested and shared with the right people. Outcomes speak for themselves. They cut through bureaucracy and shift the conversation from “why” to “how soon.” Show, don't tell. Good design, when taken to its end, is undeniable. Process and alignment matter, but they’re downstream of great work. The work always wins, not because it bypasses the system, but because it earns its way through it.
In large organizations, it's far too easy to fall prey to an illusion of progress, where activity is confused with impact. Designers show up to reviews, document strategy, align with cross-functional partners, and attend planning meetings. These rituals feel productive and offer the illusion of forward motion, but they rarely generate momentum on their own.
These structures aren’t inherently bad. In fact, they’re essential. Roadmaps provide clarity, strategy decks align vision, and design reviews improve quality. The problem isn’t their existence. The problem is when they're put before the work itself. These tools are effective once a strong concept exists. When applied too early, they can stifle progress.
During early-stage exploration, process can inadvertently become a filter for consensus rather than a catalyst for innovation. When that happens, designers feel like they’re stuck. "I'm doing all the right things, but the design isn't moving forward." It’s a signal that attention has been focused more on navigating the system than doing the design work.
It's easy to get distracted by process, because the purpose of process is to drive progress. But when placed higher in priority than the work itself, process and alignment gathering create swirl and stagnation. Before you can align on something, you need a really compelling thing to align on. In those moments, the most useful move is a return to the fundamentals: great design work. Not a deck, or a memo, or an alignment sync. Just thorough design exploration. Lead with the work, and give people something to align on. If you're stalled in bureaucracy, you can ignore it and design your way through it.
Design Your Way Through It
Feeling stuck is often framed as a process problem. But more often than not, it's a focus problem. Energy is going into the process around the design instead of the design itself. Designers don’t need to convince everyone. They need to convince the right few. A staff engineer with influence, a product-minded PM with urgency, or a design peer who wants to take a swing. That’s enough.
When we were designing the future of Square's Online Ordering product, we decided to take a big swing and go after competition like Toast and DoorDash. Our solution would be simple and focused, with the goal of getting businesses online (and accepting orders) as quickly as possible. We'd give every business a site, by default. No onboarding, no heavy setup, and minimal site customization (just a logo and colors). The output would be a clean, simple, high-converting site with rapid performance.
This was a radical departure from everything we had done in the past. It even contradicted some of our best data: customers weren't really asking for this. Our product had always been a big, robust custom website editor with limitless possibilities. We had 14 top-level navigation items, ranging from Editor, to Marketing, to Analytics, to Fulfillment and beyond. It was hard to imagine the product being much bigger or more robust than that, but customers still asked for more of it. More customization, more tools, more control. At the same time, when we looked at the results businesses were getting with the tool (and the reasons they were churning), it always came down to two things: performance and experience. It wasn't converting, it was too slow, it was complex to use. Dare I say, it was too big and robust. What customers asked for and what they needed were two different things.
Vitaly Odemchuk is the best design leader I've ever worked with, and he was our Head of Design at the time (prior to when I stepped into that role). When he proposed this vision for a major pivot toward simplicity, it was not popular. Not even close. Every PM except for one was against it, and they spun up a ton of process to systematically push back. Docs, leadership alignment reviews, countless check-ins — all of which just amounted to circular debates saying we shouldn't pursue that direction, and we should stick to what we know. What we'd always done. It honestly felt like it'd be impossible to get them on board.
In those moments, the level of conviction and unapologetic commitment that he showed made a lasting impression on me. "We're either doing this thing or I'm getting fired," was what he said when I warned him of the significant political challenges we were staring down. He was ready to stake his career on this vision — that's how strongly he believed in it. And when I asked how we'd manage to get everyone on board, he said something I'll never forget. "Austin, the work always wins." If we design the best thing, the thing that is so good it's undeniable, docs and alignment meetings won't matter. Everyone will fall in line around the winning experience. In due time.
Now I will admit, that kind of scared the hell out of me. My instinct is to bring everyone along, not to go through them. But I soon realized, he wasn't trying to exclude anyone. He was trying to show them a better path that they hadn't considered. He was absolutely obsessed with getting each individual aligned; gaining their approval and buy-in. But he wasn't going to do it through meetings. He was going to do it with the work. And let me tell you, that was a ton of work. I've never worked so hard and on such tight timelines. We were absolutely cranking out concepts and prototypes. Everyone was in Figma, designing — Vitaly being the most active of all of us. He was the type of leader that could out-design anyone. He was ready to lead from the front.
"We're going to design our way through this," was what he told me at 11pm on a Friday after a week of rough meetings, conflicting feedback, and copious urgent design work. We always operated with an existential sense of urgency; as if our failure to deliver the right concept at the right time could kill the entire thing. And honestly, that was the case. Our entire product, responsible for $250M+ ARR and ~300 full-time employees, was coming into question at the highest levels of leadership. One PM even left the company in protest. Our fledgling vision was holding on purely through the sheer might and determination of the design team. But you know what? It worked.
After months of deep misalignment with product and engineering, the dam finally broke. People stoped asking why and started asking how soon. So how did we do it? We identified key partners and worked directly with them. A PM that was ready to innovate and take some principled risk. An engineer that had a lot of influence and was always down to build a prototype. A UX researcher that was closer to our customers than anyone on the team, and knew we were onto the right thing. We didn't do this in big meetings. We met 1:1 and shared design prototypes. With those key people on board, we built a strategy PRD, a working beta in code, a set of studies that validated the direction. We gained momentum, and surrounded it with organizational inertia. We designed our way through it.
That product launched and did better than we expected. It would be followed by a subsequent iteration that was even more radical than the first, but nowhere near as hard to get done. Isn't that funny? Sometimes the most difficult part is the small initial push. Our first launch was a footnote in a press release. The second launch was a keynote presentation and a gigantic moment for the company. But somehow, that footnote mattered more to me. It's so easy to underestimate how much work it takes to get to that first little release for something unconventional, and overestimate how much work it takes to launch the big sexy thing a year later once everyone sees the light. Obvious things are easy; disruptive things are hard. And often, the disruptive path means establishing a pivot, taking a principled risk, and putting in the work to win.
Design Is the Work, Not the Deck
At its core, this was a case of design setting the strategy. A lot of places like to say they do that, but in practice it's pretty rare (and usually only happens in functionalized organizations). Design strategies aren't set in docs or decks. I know that might be hard to hear, and of course there are exceptions, but it's the truth.
I believe a critical aspect of what made us successful was that we heavily utilized prototyping as a way to demonstrate the vision. And I'm not just talking about Figma prototypes with screens stitched together. Those are great, don't get me wrong. But nothing beats a real, working prototype. Whether it be built by a designer using a tool like Cursor, or better yet, crafted in partnership with an engineer that can attest to its feasibility. We found those engineers and we prototyped with them. Then we got real customers using our prototypes via a closed alpha, processing real transactions with real customers. 3-5 businesses making money with your design says more than any vision deck ever could.
That isn't to say you shouldn't have a deck. Vision decks are useful and storytelling is a core skill for designers. But without strong underlying work, even the best story can fall flat. Concepts that haven't been fully explored can’t be rescued by a few beautiful slides. A deck might be compelling in the moment, but it will rarely lead to traction on its own. A polished narrative without substance is just theater.
The best deck is a prototype. It communicates more than words on a screen. It aligns people more than a PRD. Because it's a real, tangible thing that people can use themselves. And, perhaps more importantly, because the work was put in to make it great. The bar for a prototype is high, and it can't be met without exhaustive design work.
This isn't a profound thing that I'm saying. Designers have known this for a long time. This is more of a reminder. I remember while I was leading the Core UI for Chrome at Google, prototypes were always the best way to drive forward progress and align the team. We could debate over a PRD for hours, but a real working experience that people could use was less abstract and a bit more difficult to deny. My goal was to get to a Chrome Canary release as quickly as possible. Canary is Chrome's unstable nightly build; we'd push new features to it at the end of every work day. Overnight, millions of users (mostly developers, early adopters and tech influencers) would be using your feature. That short-circuited a lot of debate.
A working feature or prototype carries more weight than a dozen review slides ever could. For one team, that might mean pushing code to a nightly build. For another, it might be a Cursor prototype in the hands of a few customers. Whatever it is, it's a good reminder that every team has their version of a prototype, and it's always the most effective medium.
This Isn’t a Shortcut, It’s the Harder Path
I should be clear, this isn't a hack or a workaround by any stretch. This is the harder path, but it's also the better and more effective path (and I would argue, the more honest path). It means exploring divergent ideas, not just iterating on what exists. Getting close to customers and understanding what they actually need. Putting in the work to go beyond static screens. Sharing concepts early, and testing in messy, uncertain conditions. Taking principled risks, sticking to your guns, and operating with conviction.
Design leaders often feel pressure to stay in the strategy lane, writing briefs, setting timelines, running reviews. And while those skills are important, leadership through craft is the purest form of leadership. Especially when it unlocks potential others can’t see. Of course the easier move is to write a doc and schedule a meeting, but a doc only matters if the underlying idea is good and the vision is clear. Without that, process and bureaucracy start to get in the way.
When that happens, it’s easy to blame the system. But design leaders are the system. The rituals, workflows, and expectations that define how design happens were either created or preserved by the leadership team. If designers are feeling stuck, it’s worth asking: is our culture optimized for doing great work, or is it optimized for appearing aligned?
The fix isn’t to bypass process. It’s to put in the work to reshape it. Create a culture that gives air cover to exploration, encourages velocity over rigidity, and protects the early, fragile phases of invention. Process, alignment and storytelling should be in service of the work, not substitutes for it. Let the hard work happen.
The Work Always Wins
Designers don’t need to win every meeting or dominate every conversation. They need to design the thing that wins the meeting for them.
When the work is strong, it becomes self-evident. The idea no longer needs to be sold. It simply needs to be shown. Great design has a way of aligning teams without the politics. Of rewriting roadmaps without permission. Of cutting through process not by ignoring it, but by outpacing it.
It’s not the easiest path, but it’s the best one. The work always wins.
