Summary
Ian recounts his experience starting as the first UX person at Salesforce and managing increasingly complex, diverse teams. He highlights the challenge of aligning managers Adam and Karen’s teams on performance and promotions, which exposed a lack of shared language and clarity. Struggling with one-on-ones and team anxiety, Ian researched his team’s career concerns and realized many felt pressured by linear career ladders emphasizing management tracks. Ian advocates for treating careers as design projects with flexible, jungle-gym-style paths, emphasizing individual needs rather than prescribed steps. He developed a framework capturing core and additive skills across design, research, communication, leadership, culture, and innovation—recognizing that leadership isn’t about managing but mentoring and influencing. Ian created a collaborative workshop to help individuals and teams reflect on their brand, set actionable goals, and develop a network of mentors across business and technical domains. His approach standardizes language, reduces promotion debates, improves one-on-ones, and empowers both managers and employees to proactively design their career trajectories.
Key Insights
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Career ladders are linear and imposed, but real careers should be designed as flexible, non-linear 'jungle gyms'.
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Managers evaluated their large teams completely differently, revealing a need for a shared assessment framework.
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Many technical contributors resist management paths but can still grow significantly as individual contributors with leadership in mentoring and culture.
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Effective one-on-ones need structure to provide consistent value regardless of manager's daily energy.
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Knowing your product and competitive landscape deeply is a core and sometimes overlooked UX skill.
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Communication skills, even basics like error-free emails, strongly affect credibility at executive levels.
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Leadership is about influence, mentorship, and culture-building, not just formal management roles.
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Innovation requires a fearless mindset willing to break rules and challenge existing processes.
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Personal branding shapes how stakeholders perceive you when you're not in the room and needs active reflection and adjustment.
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Workshops that bring diverse experience levels together promote learning, cohesion, and create a common language for career development.
Notable Quotes
"Careers as ladders, which is how HR wants it to be because it fits financial models, but careers aren’t linear—they’re jungle gyms."
"Why don’t we do what we do for our careers? Designers should design their own career as a project."
"Leadership does not mean standing in front of a room. It means mentoring, influencing, and helping others grow."
"If you’re amazing at your job but nobody listens or acts on your work, what’s the impact really?"
"People care so much about titles, but honestly, I’d prefer the star-bellied sneak on the business card."
"A good one-on-one needs some framework so that even if I'm tired or burned out, I can still provide value."
"Knowing your customer and your product inside and out is a given—you can’t design well without that knowledge."
"Communication is mundane but key: sending an email full of mistakes to an executive changes their entire impression of you."
"Innovation is about being fearless. There’s a rule or a process, but that doesn’t mean it’s right—keep pushing and breaking things."
"Your career is the only design project you will ever own, so own it consciously and actively."
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