Hello and welcome to Design Leadership Insights, a podcast where I share the real stories, strategies and lessons learned from building and leading design teams. I'm Paul and I've spent the last 15 plus years navigating the complex world of design leadership.
Picture this: you've just launched a website that you thought would showcase your expertise as a design leader. Three months later, you're sitting in front of your laptop, staring at analytics that tell a brutal story. Bounce rates through the roof. User feedback that cuts to the bone. A site so confusing that people can't figure out whether it's a blog with a podcast or a podcast with a blog.
That was me six months ago. Today, I want to share how the most humbling design failure of my career became the foundation for one of my most important leadership breakthroughs. This is about the moment I realized that true design leadership means transforming failure into a systematic approach to accountability and growth.
As design leaders, we often talk about learning from mistakes, but we rarely discuss what that actually looks like in practice. The reality is that failure in design leadership carries weight beyond just personal disappointment. When you're responsible for guiding teams, your failures ripple outward, affecting confidence, credibility, and the trust others place in your vision.
My podcast website redesign began like many projects do, with the best intentions and a dangerous combination of time pressure and overconfidence. I had leveraged AI tools to accelerate production, prioritizing speed over the thoughtful process I would demand from my own teams. The result was a site that emerged from a hurry, with only superficial consideration given to branding, identity, and user experience.
The brand confusion was immediate and devastating. Users couldn't understand the relationship between my Medium articles and podcast content. The identity felt fractured because it was fractured. I had attempted to merge two different content strategies without creating a coherent vision that would guide users through either experience.
More painfully, I had neglected the accessibility standards I championed in my professional work. The very principles I taught other designers to prioritize had become casualties of my rushed timeline.
Here's where the real leadership lesson begins. As a design leader, my first instinct was to quietly fix the problems and move on. But I realized this approach would waste the most valuable part of this experience: the opportunity to model how leaders should respond to failure.
The first leadership decision I made was to conduct a frank assessment with the same rigor I would apply to any team project. I approached this assessment as if I were evaluating work from a designer I was mentoring. This meant setting aside ego and applying the same standards I expected from others.
I started by gathering direct feedback from colleagues and users. One colleague told me, "The layout is confusing. I can't figure out whether this is a blog with a podcast or a podcast with a blog. The identity feels fractured." Another user said, "I gave up trying to find episode transcripts. If accessibility matters to you, it should be obvious in your design."
Initially, this feedback stung. But I realized that as a leader, my response to criticism would either model resilience and growth or defensiveness and stagnation. I chose to treat each piece of feedback as valuable data rather than personal attack.
With my failures clearly documented, I had to establish goals that aligned with my leadership values rather than just fixing surface problems. This process revealed something crucial about design leadership: our personal projects become laboratories for testing whether we actually practice what we teach.
Creating a new website from scratch with a strong visual identity became my north star. This was about more than building something that looked professional. It was about crafting a digital presence that would demonstrate the thoughtful approach I advocated for in my teams.
Ensuring accessibility was baked in from the start became non-negotiable. I had failed my own accessibility standards, which meant I had failed to honor the inclusive values that formed the foundation of my leadership philosophy. This goal represented a commitment to practicing what I preached.
I committed to making each episode its own standalone landing page, addressing the content strategy confusion that had plagued the previous version. This decision required me to think systematically about information architecture in ways I had skipped during my initial rushed approach.
These goals emerged from a conviction that had been tested by failure: digital experiences should be both beautiful and functional for everyone. They represented my personal commitment to craft something that truly reflected my values as a leader.
Before opening design tools or writing code, I immersed myself in research with the same thoroughness I would expect from my teams. I examined industry standards, reached out to peers for feedback, and analyzed user behavior patterns.
This research phase became a lesson in leadership humility. I had to acknowledge that my expertise in managing design teams didn't automatically translate to executing great individual design work under pressure. The skills required for leadership and hands-on execution overlap but are not identical.
The feedback process revealed how my leadership position had insulated me from direct user criticism. When leading teams, feedback typically flows through layers of meetings and formal reviews. Working directly with users who struggled with my design provided immediate, unfiltered insight into the gap between intention and execution.
During the implementation phase, I treated each design decision as an opportunity to practice the decision-making frameworks I taught my teams. When faced with the choice between a dark theme I personally preferred and a light theme that would be more accessible to broader audiences, I chose to implement theme switching that honored both preferences.
This decision embodied a leadership principle I often discussed but rarely had to personally navigate: designing for others rather than for yourself. As a leader, it's easy to advocate for user-centered thinking when you're not the one making the detailed implementation choices.
I approached accessibility requirements with the same rigor I would apply to enterprise projects. This meant going beyond compliance checklists to think about real people navigating the site with different abilities and technologies. I implemented skip-to-content links, ensured proper color contrast, and created transcript integration that felt natural rather than obligatory.
Each technical choice became a test of my leadership principles. Using CSS image masking for vendor logos and leveraging PHP templates for easy updates reflected my belief that sustainable design requires thinking beyond the immediate launch to long-term maintenance and evolution.
Perhaps the most significant leadership insight emerged during the iteration process. Each version of the site brought me closer to my vision while revealing new opportunities for improvement. This experience reinforced something I often told my teams but had to personally rediscover: great design emerges from iteration, not inspiration.
As a leader, I often watched team members struggle with the discomfort of showing unfinished work. Living through this discomfort myself renewed my empathy for designers who resist sharing early concepts. The vulnerability of putting incomplete ideas into the world requires emotional resilience that leaders must model, not just request.
The technical implementation phase taught me about the relationship between design vision and execution constraints. When I discovered that certain design ideas couldn't be implemented within my timeline and budget constraints, I had to make trade-offs that my team members face daily but that I usually observed from a distance.
The transformed website became more than a successful redesign. It became evidence that leadership growth requires engaging directly with the challenges we ask our teams to navigate. The technical skills I developed during this process improved my ability to have meaningful conversations with developers about implementation feasibility.
More importantly, the experience of systematic failure and recovery gave me a framework for helping team members navigate their own challenging projects. I learned to recognize the signs of rushed decision-making because I had lived through the consequences of prioritizing speed over process.
The accessibility improvements I implemented became examples I could reference when advocating for inclusive design in enterprise projects. Having personally experienced the complexity of balancing aesthetic preferences with accessibility requirements gave weight to my arguments for building inclusive practices into project timelines.
The most powerful lesson from this experience centers on the concept of design accountability as leadership development. When we take responsibility for our failures with the same rigor we apply to our successes, we model the intellectual honesty that drives team growth.
Start by applying your team's quality standards to your own individual work. If you expect your designers to conduct user research, conduct user research on your own projects. If you advocate for accessibility, implement accessibility features in your personal work. This alignment between teaching and practice builds credibility that no amount of theoretical knowledge can create.
Create systematic approaches to learning from failure. Document what went wrong, why it went wrong, and what specific changes will prevent similar problems in the future. Share these insights with your teams to demonstrate that failure becomes valuable only when we extract actionable lessons from the experience.
Use personal projects as laboratories for testing the advice you give others. The frameworks and processes you recommend to your teams should be frameworks you've personally validated through your own design challenges.
Finally, recognize that leadership credibility comes from demonstrated problem-solving under real constraints, not just theoretical expertise. Your team members face budget limitations, timeline pressures, and technical constraints daily. Experiencing these challenges yourself deepens your ability to provide meaningful guidance when they encounter similar obstacles.
Design leadership requires us to continuously test our assumptions against reality. Your next personal project, whether it's a website, mobile app, or design system, represents an opportunity to validate whether you actually practice what you teach.
Choose a project that challenges you to apply the principles you advocate for in your leadership role. Use the same research methods, design processes, and quality standards you expect from your teams. Document your decision-making process so you can share both successes and failures with the designers you lead.
The goal is alignment between your leadership advice and your personal design practice. When that alignment exists, your guidance carries the weight of lived experience rather than just theoretical knowledge.
Great design leaders are made not just through managing successful projects, but through personally navigating the uncertainty, constraints, and trade-offs that define real design work. Your willingness to engage directly with these challenges while maintaining the same standards you expect from others builds the kind of credibility that transforms teams and elevates design practices across entire organizations.
The journey from failure to success in your own work becomes a roadmap you can share with every designer who faces similar challenges. That transformation from personal accountability to team growth represents the evolution from design manager to design leader.
Thank you for listening to Design Leadership Insights. I'd love to hear about your own experiences with design accountability and leadership growth. You can reach out by emailing info@designleadershipinsights.com. The topics we covered today and more are explored in much more depth in my book Beyond the Wireframe, available at all good bookstores and at beyondthewireframe.com.
