Design Management · 2U
Developing designers through craft, confidence, and trust
Over 8 years at 2U I’ve managed and mentored designers across marketing, product, and design systems. The most meaningful part of the job has always been helping them grow. Here’s one story of what that looks like.
Role
Manager & mentor
Team
Marketing, product & systems designers
Timeline
6 years
Outcome
Mid-level → Principal
The starting point
Her biggest challenge wasn’t effort or intelligence. It was fear of being wrong.
Results
2
promotions over six years
Principal
Product Designer, focused on design systems
8+
years managing and mentoring designers at 2U
Starting point
Solid, reliable, and afraid to be wrong.
When I began managing Lilith James, she was a solid mid-level designer: reliable, detail-oriented, and thoughtful. She approached design cautiously, aware of every constraint and expectation, and that limited her willingness to explore bold ideas.
My coaching
Change how she approaches the work.
Rather than prescribing answers, I focused on how she worked.
Normalize messiness early in the process
Separate exploration from evaluation
Generate many ideas quickly before editing down
Treat experimentation as a skill, not a personality trait
In critique
Ask why, not what’s wrong.
Asked why she made decisions instead of correcting them
Highlighted moments where risk paid off
Gave clear, actionable feedback tied to craft, not taste
I also advocated publicly: encouraging bigger, scarier projects, backing her voice in cross-functional conversations, and naming her wins with peers and leadership.
“Phil has shown me what being a great leader looks like. He has been my manager for four years but also has been a mentor and role model as I have grown my career.”
Lilith James
Principal Product Designer, formerly 2U
The transformation
Confidence rooted in craft.
Explorations became more expressive and intentional
Ideas were stronger and more confidently defended
She sought out complexity instead of avoiding it
Her presence in critiques and cross-functional work grew noticeably
Over six years she was promoted twice, becoming a Principal Product Designer focused on design systems, then moved on to a design systems role at HashiCorp/IBM.
At scale
Not an isolated story.
Helped a junior designer grow into senior scope through confidence in critique and ownership
Mentored designers moving into systems-focused roles, creating new career paths
Supported designers through burnout or stagnation by reframing success and rebuilding momentum
Philosophy
Creating conditions where great designers emerge.
Stay close to the work
Create safety without lowering the bar
Meet designers where they are
Advocate, don’t just evaluate