I've been spending time talking to designers and product owners, and I've noticed a trend. People are all about iteration - until it's actually time to iterate. Then come the excuses.
Budget, team structure, leadership, stakeholders, and more collide into an environment where teams constantly prioritize new, "sellable" value rather than continuous improvement. The result? Products with short-term adoption, workaround experiences, growing competition, and mountains of unmanageable tech and design debt.
One of my most transformative moments in my career was when I was thrown into the world of usability testing. The first several tests I dreaded - they would just prove I'm bad at my job right? I'll get fired! But something magical happened - every time I was "proven wrong," I would have a burst of energy and thousands of ideas on improvements. I started walking into sessions hoping my design would get torn apart and I would see something so obvious that was invisible to my world view and perspective.
When people think of design, they often picture the big reveal: polished mockups, a slick prototype, a shiny “final” product. But the truth? The real magic happens in the messy middle — iteration.
Iteration isn’t glamorous. It’s the part where we redraw, reframe, and rethink until things finally click. And it’s not just a design process — it’s a leadership philosophy.
Here’s why:
💪 Iteration builds resilience. Teams that learn to treat ideas as drafts — not verdicts — bounce back faster when things shift. Instead of fearing “wrong,” they see it as “not yet.” And as humans, we need a little help detaching sometimes.
🚀 Iteration accelerates innovation. Big leaps often come from small adjustments stacked over time. A 5% improvement repeated ten times looks like a breakthrough.
🤝 Iteration strengthens collaboration. When everyone knows nothing is sacred, input flows more freely. People share earlier, ask sharper questions, and contribute without fear of “ruining” the big idea.
🌱 Iteration models growth. Leaders who show their own process — drafts, reworks, changes of mind — send a powerful signal: progress matters more than perfection.
Some of the best products (and teams) I’ve seen weren’t built by getting it “right” the first time. They were built by staying open to revision, again and again.
💡 My takeaway: Iteration isn’t rework. It’s the work. And when teams embrace it — with patience, humor, and curiosity — that’s when real breakthroughs happen. It's not about failing fast - it's about learning fast. Together.
What’s the best thing you’ve seen come out of an “iteration that wasn’t supposed to work”?