Developing Designers Through Craft, Confidence, and Trust
Management, Design Leadership
Overview
Over the last 7.5 years at 2U, I’ve managed and mentored designers across marketing, product, and design systems. While my role required operational leadership, the most meaningful part of my work has always been helping designers grow — creatively, professionally, and personally.
I believe strong design cultures are built through thoughtful critique, psychological safety, and leaders who stay close to the work. This case study highlights what that looks like in practice.
Flagship Story: Growing a Designer Into a Principal Leader
Starting Point
When I joined 2U and began managing Lilith James, she was a solid mid-level designer with a strong foundation in structured design environments. She was reliable, detail-oriented, and thoughtful — but hesitant to experiment creatively.
Her biggest challenge wasn’t effort or intelligence.
It was fear of being wrong.
She approached design cautiously awareness of constraints, expectations, and approval, which limited her willingness to explore bold ideas or push beyond established patterns.
"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. Phil does not just care about managing performance of his direct reports; he learns about each individual and works to understand their career goals to empower their growth. Phil is a force of positivity bent on improving the lives of everyone around him."
Lilith James, Principal Product Designer
previously 2U, currently HashiCorp/IBM
My Coaching Approach
Rather than prescribing answers, I focused on changing how she approached the work.
I worked closely with Lilith to:
Normalize messiness early in the design process
Separate exploration from evaluation
Generate many ideas quickly before editing down
Treat experimentation as a skill, not a personality trait
In critiques, I intentionally:
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 for her growth publicly:
Encouraging her to take on larger, scarier projects
Supporting her voice in cross-functional conversations
Recognizing her wins with peers and leadership when she pushed beyond her comfort zone
The goal was not just better work — it was confidence rooted in craft.
The Transformation
Over time, her work changed dramatically.
Design explorations became more expressive and intentional
Ideas were stronger, clearer, and more confidently defended
She sought out complexity instead of avoiding it
Her presence in critiques and cross-functional discussions grew noticeably
As her confidence increased, so did her appetite for responsibility. She naturally stepped into more senior conversations, took ownership of larger initiatives, and became a trusted voice within the team.
Outcome
Over six years, Lilith was promoted twice — ultimately becoming a Principal Product Designer focused on Design Systems.
By the time she moved on to her next role:
She was one of the most trusted designers on the team
Known for both high-quality craft and dependable execution
A confident partner to product, engineering, and marketing
A mentor and expert voice for other designers
She later joined another company as a Design Systems Product Designer, continuing the trajectory she built during her time on my team.
My Leadership Philosophy
This story reflects how I approach people and craft leadership more broadly:
Stay close to the work — design leaders should actively critique and coach
Create safety without lowering the bar — growth requires trust and challenge
Meet designers where they are — coaching is personal, not one-size-fits-all
Advocate, don’t just evaluate — growth accelerates when leaders create opportunity
I see my role not as directing output, but as creating conditions where great designers can emerge.
Additional Growth Stories (At Scale)
This wasn’t an isolated experience:
Helped a junior designer grow into senior scope by developing confidence in critique and ownership
Mentored designers transitioning into systems-focused roles, shaping new career paths within the organization
Supported designers navigating burnout or stagnation by reframing success and rebuilding momentum
Across teams, my focus has remained the same: craft, confidence, and long-term growth.
Why This Matters
Strong systems and processes only work when the people behind them are confident, capable, and supported.
This case study represents the kind of leadership I value most — hands-on, human, and deeply invested in the growth of others.