Everyone Must Win
An essay by Austin Knight
Summary
In great negotiations, no one walks away feeling like they lost. Everyone walks away feeling like they won. That’s not compromise; it’s positive-sum negotiation. The best leaders, teams, and companies grow not by dividing value, but by creating it. “Everyone must win” is both a negotiation strategy and a design principle for how to build trust, scale influence, and ship meaningful work.
It's natural to approach negotiation like a contest. Someone gets more, someone gets less, and if you’re smart or persuasive enough, you end up on top. That mindset is baked into how many companies operate. Budgets, roadmaps, and headcount all are framed as zero-sum games. But when you’re working on a team that builds things together, this mindset doesn’t work very well. If one person wins, the system loses.
Game theory offers a useful lens here. The Prisoner’s Dilemma shows how rational actors, trying to maximize their own gain, end up with worse outcomes than if they had simply cooperated. The best outcomes come from positive-sum games, which are scenarios where total value increases because the parties design a better system together. The goal isn’t to split the pie fairly; it’s to make the pie bigger.
In negotiation theory, this is called integrative bargaining. Instead of fighting over concessions, you reframe the problem so each side’s success becomes mutually reinforcing. That’s the essence of good design too.
A product team that sees design, product, and engineering as opponents will spend its energy protecting territory. A team that operates under the principle that “everyone must win” spends that energy expanding possibility. The first divides; the second compounds.
"Everyone Must Win" is a Design Principle
Design is negotiation in disguise. Every interface is a set of trade-offs between beauty and performance, usability and flexibility, creativity and constraint. The best designers don’t just balance those tensions; they resolve them. They find solutions that satisfy multiple truths simultaneously.
The iPhone wasn’t a compromise between a phone and a computer; it redefined both. Chrome’s minimal UI wasn’t a concession to speed; it was the design manifestation of performance itself. In each case, design elevated the constraint into the concept.
Inside modern product organizations, Design, Product, and Engineering often have competing incentives. Product optimizes for speed and measurable outcomes. Engineering optimizes for scalability and maintainability. Design optimizes for experience and usability. Each function is right…yet incomplete.
While leading design for Square Online, this dynamic came to a head. The company had recently functionalized, shifting away from a GM-led org toward a fully functional model, and quality was suddenly the mantra. But our product, inherited from the Weebly acquisition, was slow. It ran on Ember, while the rest of Square was built on React. The team was gearing up to launch Online Ordering, a dramatically simplified and focused product for F&B sellers, and there was a hard question on the table: should we build it the easy way (on the legacy Weebly codebase) or the right way (on React)?
On paper, Ember was the faster option. The infrastructure was already there, the engineers were familiar with it, and the product team was eager to move. But building on Ember again would have locked us into the same isolation and latency problems we were trying to escape.
So I reframed the conversation. Instead of arguing for “design quality,” I argued that speed is quality. A fast product isn’t just technically better; it feels better. It communicates trust. It’s a design decision as much as an engineering one. To make that real, my team and I went back and simplified the design scope even further. We stripped the product down to its essence, leaving only the capabilities our sellers truly needed to get online and start taking orders. That focus made the path forward undeniable: with this scope, we could build the right foundation (on React) quickly and confidently.
When we presented it to leadership, I didn’t say “Design wants React.” I said, “If we care about quality, this is what quality means.” Engineering leadership backed it. Product leadership saw the momentum we could gain by shipping something small but excellent.
We shipped Order Online on React in a way that was fast, maintainable, and connected to the rest of Square. React became the company standard soon after, and the engineers who made that leap early were proud of it. That was a true “everyone wins” moment. Design got the quality and focus we wanted. Engineering got a modern foundation that made their lives easier. Product got a faster launch and a platform that could grow.
Negotiating Upward
The same principle applies when you’re managing up. Many designers assume leadership doesn’t “get” design because executives care about numbers like growth, revenue, and efficiency. But that’s not ignorance; it’s scope. Their job is to ensure the company survives and thrives. If you want design to be taken seriously, you can’t resent that. You have to connect to it.
I learned this lesson early in my career at HubSpot. Back then, I was pitching designs to some of the most senior leaders in the company, such as Brian Halligan (CEO), Dharmesh Shah (CTO), Mike Volpe (CMO), and Jeremy Crane (VP of Product). We’d go in with glossy decks, full of typography systems and emotional rationales. The designs were beautiful, the pitches were inspiring…and nothing happened afterward. Leadership would smile, say “great work,” and move on.
One day, we presented a project that captured the problem perfectly. Our creative director, who came from an agency background, had me create an elaborate “ecosystem map.” It was a circular diagram showing all the marketing channels surrounding HubSpot: ads, events, content, partnerships. It was visually stunning. Leadership looked at it and said, “This looks like a design exercise for the sake of a design exercise.”
They were right. We were speaking a language they didn’t understand (or need to). Designers love to talk about empathy, but we often fail to extend it to our own leadership. We know our users, but not our executives. We ignore what motivates them and then blame them for not understanding us.
So I tried something new. Every month, HubSpot’s leadership team shared internal strategy decks which outlined metrics like LTV, conversion, churn, and the big idea of the moment: the “flywheel.” I started reading those decks closely, and when I presented design work, I used the same language. I didn’t talk about “beautiful interactions” or “emotional resonance.” I talked about how the design would improve activation, how it could drive LTV, how it was created to power the flywheel.
Same design. Different framing. Totally different reaction.
Leaders who once politely nodded were now leaning forward, asking questions, and offering support. They saw how design could move the business forward. That’s when I solidified my conviction that empathy isn’t just for users. It’s for anyone you need to influence. And influence comes from making others feel like the success of your idea is also theirs.
Great design leaders don’t translate design into business terms after the fact. They design in business terms from the start. They understand that design is a function of the business, not a separate craft hovering above it. When leadership wins, design wins (and vice versa).
Your success depends on making others feel like your win is their win too.
The Danger of False Wins
Of course, “everyone must win” doesn’t mean “everyone gets what they want.” Too often, teams mistake consensus for collaboration. Consensus feels good because it’s comfortable. Everyone nods, no one disagrees, and progress quietly dies.
Alignment, by contrast, is uncomfortable. It requires friction, debate, and real clarity. It’s not about smoothing out differences; it’s about integrating them into something better.
False wins happen when teams chase harmony instead of truth. They produce watered-down designs, ambiguous strategies, and products that try to please everyone and delight no one. The best teams know the difference: when you walk out of a room aligned, the energy is higher, not lower. Everyone knows what they gained, and what they gave up, and why it was worth it.
Positive-Sum Leadership
Leadership, at its core, is positive-sum. It’s the art of expanding the system so that everyone’s success reinforces everyone else’s.
When you design for shared wins, you earn trust. When you argue for your own win, you invite defensiveness. Every cross-functional relationship (whether it be with Design, Product, Engineering, or the C-Suite) is an opportunity to design a better outcome, not just a better argument. If people leave a meeting with you feeling like they won, they’ll follow your lead next time. That’s how influence scales. That’s how teams compound instead of divide.
Design leadership isn’t about protecting design's slice of the pie. It’s about enlarging the pie. Everyone must win, or no one really does.
