Episode 11

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.

Day one as a new design leader. The office buzzes with anticipation. Whiteboards display user flows, sticky notes cover walls, Figma files await exploration. Your team watches intently—some excited, others nervous. Executive stakeholders expect immediate results. Engineers wonder if you'll disrupt their process. Product managers hope you'll align with their roadmap.

What you do in these crucial early days determines your success and your entire team's trajectory for years to come.

I've stepped into this exact scenario multiple times throughout my career, and I've discovered that the most impactful design leaders build understanding first. The truly transformative approach to your first 90 days shouldn't be implementing sweeping changes or criticizing existing processes, instead you should be creating a foundation of knowledge, relationships, and strategic vision that fuels sustainable transformation.

Throughout my journey, I've learned that transitioning into a new design leadership role presents a unique tension. You feel pressure to demonstrate immediate value while simultaneously needing to understand the organization's complex dynamics.

As a design leader, I've taken over teams where designers operated in isolation from development, where product managers dictated design decisions, and where user research was considered a luxury rather than a necessity. I remember one instance where I arrived to find designers creating beautiful mockups that developers couldn't implement, product managers unable to articulate design requirements to offshore teams, and executives demanding faster delivery without understanding design's strategic value.

The temptation in these situations is to immediately implement new processes, reorganize the team, or push for different design tools. I've witnessed new leaders make these moves, only to face resistance that undermined their effectiveness for months afterward.

My approach evolved after experiencing both successes and painful failures. I developed a three-phase framework that has guided me through multiple leadership transitions, including building teams from scratch and transforming struggling design organizations.

The central principle I learned was that understanding, must precede action.

Let's explore how this unfolds across the crucial first 90 days.

Phase 1. Days 1-30. The Art of Listening.

The first month as a design leader is about immersing yourself in the organization's reality.

When I joined my current role, I avoided immediately critiquing the existing interfaces or pushing for a design system and instead spent time understanding the organization's unwritten rules, relationships, and daily rhythms.

I started by shadowing customer service representatives as they handled user calls. This decision revealed invaluable insights that no slide deck could provide. Listening to actual users struggle with navigation issues, watching their frustration with inconsistent interfaces, and hearing customer service representatives explain workarounds provided concrete evidence of experience problems.

I came to learn that 37% of support calls stemmed from users struggling to complete basic tasks—a powerful metric that later helped secure executive buy-in for major design initiatives. This represented significant operational costs and customer frustration.

Next, I scheduled informal conversations with developers across several teams. I asked questions about their challenges with the current process. These conversations revealed that designers handed off work without proper context, and last-minute changes regularly derailed sprint planning. This highlighted the process issues and the relationship breakdowns between disciplines.

I met with individual product managers to understand their goals, constraints, and frustrations. I discovered they lacked confidence articulating user needs, which led them to focus exclusively on feature lists rather than experience quality.

Continuing with digging deeper into the metrics, I conducted similar discussions with executives, focusing on their business objectives rather than design specifics. This revealed misalignments between company priorities and how teams actually operated.

By the end of this month, I had developed a comprehensive understanding of the organization's reality and how work actually flowed through the system. This was active information gathering that required strategic questioning and careful listening.

My leadership approach during this phase centered on demonstrating respect. I acknowledged the constraints teams operated under, recognized the history behind current practices, and validated the challenges everyone faced. This built trust that proved essential for the changes that would come later.

Phase 2. Days 31-60. Crafting the Vision.

By the second month, patterns had emerged from my observations. I saw that developers made crucial interface decisions without guidance because they lacked design direction. Designers created beautiful mockups disconnected from technical constraints. Product managers couldn't articulate design requirements clearly to offshore teams.

As a design leader, my role was to identify these patterns and translate them into a compelling vision for change. I created a strategic document that connected design improvements to the business metrics that executives cared about. Development velocity, customer acquisition costs and support ticket reduction.

I involved key stakeholders from across the organization in shaping it, and facilitated workshops with designers, developers, and product managers to identify shared goals and pain points. This collaborative approach accomplished two critical leadership objectives: it improved the strategy through diverse input and created stakeholder ownership essential for implementation.

The strategy deliberately balanced quick wins with structural changes. For developers making interface decisions without guidance, I proposed a simple pattern library as an immediate resource while laying groundwork for a comprehensive design system. For designers creating implementation-challenged mockups, I instituted technical feasibility reviews early in the design process.

My approach to presenting this vision illustrates a crucial leadership principle: connect design improvements to business outcomes. When meeting with the executive team, I didn't lead with aesthetic considerations or user experience theory. Instead, I started with the 37% of support calls stemming from usability issues, calculated the operational cost, and showed how our strategy would address this concrete business problem.

This framing transformed design from a subjective discipline into a strategic business function. It aligned the focus to reducing support costs, improving operational efficiency, and enhancing customer retention.

Phase 3. Days 61-90. Strategic Action.

The final month focused on demonstrating progress while building momentum for longer-term change. As a design leader, I identified three critical screens in our logistics platform causing significant user friction. I steered away from attempting system-wide changes immediately and instead led the team through redesigning these screens as a focused pilot project.

This targeted approach accomplished several leadership objectives simultaneously. It provided a tangible example of our design vision, created evidence of impact through improved completion rates, and gave the team experience with new collaborative processes.

I established regular design review and feedback cadences, but made them meaningful rather than bureaucratic. Each review focused on specific user problems and business outcomes rather than subjective opinions. This structure taught the team to evaluate design through the lens of user and business impact.

A pivotal leadership moment came when presenting the results of our pilot project to executive stakeholders as I highlighted the collaborative process that created them. This demonstrated how our approach was transforming how teams worked together.

From my experience leading design teams through transitions, here are the essential principles that will help you navigate your first 90 days as a design leader:

Invest in understanding before acting. The depth of your knowledge in the first month determines the impact of your actions in months that follow. Schedule time with customer service representatives, developers, product managers, and business stakeholders to understand their unique challenges and perspectives.

Build relationships across disciplines. Your effectiveness as a design leader depends on your ability to collaborate with product, engineering, marketing, and executive teams. Invest time in understanding their goals and constraints before proposing changes that affect them.

Translate design value into business terms. Connect your design initiatives directly to business metrics like support cost reduction, development velocity, and customer retention. This translation is essential for securing resources and support.

Choose focused initiatives over comprehensive changes. Demonstrate your approach through targeted projects that show tangible results rather than attempting system-wide transformation immediately. These success stories build credibility for larger initiatives.

Balance action with understanding. While deep comprehension is critical, teams also expect visible progress. Identify targeted opportunities where you can demonstrate impact without requiring extensive organizational change.

As we conclude this first season of Design Leadership Insights, I want to reflect on the journey we've taken together across these eleven episodes.

We began by exploring how to scale design impact within organizations, growing from a solo contributor to leading teams across multiple regions. We examined the 89% Solution for building and retaining high-performing design teams through structured development frameworks and meaningful growth opportunities.

We delved into creating psychological safety as the foundation for innovation, establishing environments where teams feel empowered to take intellectual risks. We explored the art of design critique through structured frameworks that elevate feedback from subjective opinions to meaningful growth opportunities.

Our journey took us through reimagining complex user experiences like flight booking interfaces, implementing progressive disclosure principles in enterprise design, and positioning design leadership as a bridge between user needs and business objectives.

We examined how technical backgrounds can strengthen design leadership, the value of creative side projects in developing leadership perspective, and transforming customer satisfaction data into meaningful design decisions.

Today's episode on navigating your first 90 days as a design leader completes our exploration of the design leadership journey—from building teams to creating environments for innovation to translating user insights into business value.

The common thread throughout this season has been a fundamental principle: exceptional design leadership doesn't mean imposing your vision or implementing trendy methodologies. You should be creating environments where design can thrive, building sustainable processes, connecting user needs with business objectives, and continuously delivering value through user-centered solutions.

As you apply these principles in your own leadership journey, remember that your greatest impact comes from the designs you create, the teams you build, the processes you establish, and the culture you cultivate.

Thank you for joining me throughout this season of Design Leadership Insights. If these episodes have provided value to you, I'd be grateful if you'd leave a five-star review wherever you get your podcasts. Your feedback helps other design leaders discover these conversations.

I'm already developing ideas for season two, where we'll explore new dimensions of design leadership including scaling operations internationally, navigating organizational transformations, and integrating emerging technologies into design processes.

Until then, continue building bridges, creating psychological safety, and transforming organizations through thoughtful design leadership.

Thank you for listening to Design Leadership Insights. If you'd like to get in touch, you can email info at design leadership insights dot com.