The State of Design Leadership 2026:
Pressures & Patterns in a Shifting UX Landscape
A webinar based on in-depth interviews about the pressures shaping design leadership today.
Hosted by: Alex M. Chong
A Lens Into Other Design Leaders’ Experiences
The design leader role is often experienced in isolation, with limited visibility into how peers are navigating similar responsibilities and constraints.
Outwitly’s Director of Design, Alex M. Chong, presents a synthesized perspective on the findings and patterns surfaced from conversations with design leaders across verticals.
Discover the common pressures shaping design leadership today, across personal, organizational, and industry contexts.
An Unconventional, Reflective Session
Design leaders today are expected to operate with greater strategic influence, while navigating accelerating AI pressure, organizational politics, hiring friction, and UX metrics that reward visible output over meaningful outcomes.
This webinar offers a peer-level perspective on these realities, without prescribing a one-size-fits-all approach. Alex will guide you through:
- The core common pressures shaping design leadership across personal, organizational, and macro layers.
- How those pressures show up systemically in hiring, AI, metrics, organizational politics, and support gaps.
- The recognizable patterns and archetypes that emerged from synthesizing our interviews with design leaders.
Leave with a shared language for articulating and reflecting on the shifting role of UX leadership, — and the factors that influence how each of us shows up.
Meet the Speaker — a Fellow Design Leader
Alex M. Chong is the Director of Design, UX Leadership & Practice at Outwitly. In his 12+ years in the field, he has worked with a range of startups and Fortune 500s — designing, advising, and coaching teams building complex products and services.
His focus areas include:
- Working fractionally with organizations to integrate design as a strategic operation
- Shaping practice architecture, operational strategy, and team capability to enable sustained innovation
- Advising and coaching individuals, teams, and leaders in building complex products and services
Alex grounds his perspective in close, ongoing work with design leaders as practices evolve — with attention to how emerging technologies and AI tooling landscapes can reduce noise and amplify creative signal.
