Design’s New Differentiator: Moving Upstream in the Age of AI (with Stephen Patterson)

I talk with design leader Stephen Patterson about what still matters for designers as AI makes “good enough” interfaces easy to generate. We discuss the growing sameness across digital products—similar fonts, grids, and Tailwind/Bootstrap-like aesthetics—and how hiring managers look for taste, originality, and the ability to explain problem-solving beyond polished outputs. Stephen traces his path from agency work designing apps in Photoshop to building in-house teams at Braintree, where designers were expected to code, and later to Bloomscape and Highnote, where speed and prototyping matter. We explore how design skill is shifting upstream to brand systems, voice, principles, and rules that guide AI output, and Stephen’s test for thriving: not being afraid of the terminal. He closes by sharing he’s leaving fintech to join Deck, an AI agent startup, as its first principal product designer.

00:00 What Matters in Design Now
02:47 AI Sameness and Taste
06:12 Hiring for Nuanced Judgment
08:32 Six Months on the Road
11:42 How Stephen Got Into Design
13:31 Early UX in Photoshop Era
16:26 Agency to In-House at Braintree
18:14 Why In-House Moves Faster
21:27 Staying Six Years and Moving On
24:49 What’s Next After Braintree
25:31 Leaving FinTech for Bloomscape
27:21 Wearing Too Many Hats
28:24 Designers Who Code Origins
30:37 Startup Generalist Advantage
32:43 Hiring for AI Era Skills
33:51 AI Tools in Workflow
39:51 Why Design Still Matters
45:04 Brand as Competitive Edge
48:07 New Role at Deck
51:02 Host Takeaways and Wrap

Helen Huang on Trove, Behavioral Identity, and Building an Authentic Life in the Age of AI

On today’s episode, we speak to Helen Huang, a product leader and two-time founder building Trove, a “behavioral identity layer” that helps people understand and represent themselves through what they do rather than what they say. Helen recounts immigrating from China to Canada, studying earth science at Waterloo, pivoting into product roles at Zynga, Microsoft, and GitHub, then bootstrapping edtech company CoLab to seven figures while graduating 2,500+ learners before taking a 2024–2025 gap year to learn AI and explore playful experiments (including a garbage-bag fashion show). She describes Trove’s interactive story “Tangles,” early traction and intense user responses, and her aim to invert typical AI use: AI prompts us, and we supply instinctive answers. All while fundraising and hiring a founding team!

00:00 Show Mission Shift
00:48 Meet Helen and Trove
02:38 Reconnecting and Background
06:05 Earth Science to Tech Pivot
08:14 800 Applications and Resume Limits
10:28 PM Lessons to Founder Leap
14:55 Building CoLab and Scaling Education
18:19 AI Hype and Learning Friction
24:59 Gap Year Doubts and Rediscovery
28:01 Garbage Bag Fashion Show
28:26 Immersive Fashion World
29:44 Fun Over Goals
31:48 Civic Tech Detour
34:11 Finding Trove Mission
35:46 What Trove Is
37:54 Actions Reveal Identity
39:58 Early Drops And Metrics
41:59 Real Life Impact Stories
44:47 What Comes Next
46:25 AI Prompts Us
49:36 Use Cases And Ethics
52:51 Closing Reflections

Building Change Capacity: Jillian Reilly on Permission, Automation, and Portfolio Careers

Earlier this year, I interviewed Jillian Reilly, author of The Ten Permissions: Redefining the Rules of Adulting for the 21st Century about why people change (or don’t). And how “permission” and agency shape behavior more than resources, training, or workshops.

In part two of my conversation with Jillian Reilly, we talk about why “change management” often becomes performative and why real transformation depends on building ongoing capacity for change. She describes her role as a catalyst who creates conditions for teams to have hard, honest conversations, run experiments, and rebuild trust, emphasizing that leaders must explicitly allow disagreement and learning rather than rely on one-time programs. We discuss how automation will replace repeatable “corporate cog” work and increase the value of human adaptability, critical thinking, and innovation. 

Jillian frames the current era as an “unraveling” of old social and career scripts and a “renaissance” of choice that requires agency rooted in clear-eyed optimism. She offers practical career guidance: design flexibility early, think in portfolios (“I can” vs. “I am”), build temporary/project-based value like a DJ reading the room, and experiment without dopamine-chasing by matching focus to one’s current season.

00:00 Change Management Trap
01:17 Consultant as Catalyst
05:19 Permission Over Performance
09:26 Building Change Capacity
11:00 Automation Ends Cogs
12:48 Unraveling and Renaissance
21:10 Optimism Creates Agency
27:15 Reclaim Local Control
28:21 Designing Flexible Careers
31:47 Portfolio Skills Mindset
35:14 Build Temporary Projects
40:57 You Already Know This
45:11 Experimentation Versus Dopamine
51:41 Closing Takeaways

Earlier this year, I interviewed Jillian Reilly, author of "The Ten Permissions: Redefining the Rules of Adulting for the 21st Century," about why people change (or don’t). And how “permission” and agency shape behavior more than resources, training, or workshops.

She recounts leaving a prescribed path and law school plans to go to South Africa during the of apartheid, followed by two decades in international aid across Africa. During that time, she led an HIV/AIDS program in Zimbabwe, where she saw how cultural and safety constraints make “novel choices” dangerous. She describes disillusionment with the kind of change driven by funding incentives, moving into consulting, and later prioritizing motherhood despite career trade-offs. We explore the ideas of permission, conviction over certainty, experimentation, avoiding regret through intentional choice, and building “permission-rich” environments in villages and boardrooms alike.

00:00 Why Permission Matters
00:17 Meet Jillian Reilly
01:59 Ten Permissions Explained
04:53 Leaving the Midwest Script
08:11 Aid Work Lessons
10:03 Zimbabwe and Permission
13:32 Agency and Modern Careers
17:46 Moving to South Africa
22:33 Conviction Over Certainty
24:02 Feel Your Way Forward
27:05 Transition to Consulting
27:28 Aid Work Disillusionment
29:39 Spending Versus Impact
31:52 Leaving the Dream Job
36:09 Consulting as Truth Teller
36:55 Permission and Change
41:12 Motherhood and Tradeoffs
46:33 No Regrets Framework
50:57 Returning Through Experiments
53:22 Frontiers and Explorers Way
55:50 Closing Reflections and Tease

The Trust Tax: Reframing Your Story and AI Layoff Narratives

Today I unpack a LinkedIn post about declining trust in ourselves and each other, showing how it appears in job searches and in how companies explain AI-driven change. Drawing on Stephen M.R. Covey’s The Speed of Trust, I argue trust is has a tangible impact across our careers and the broader economy. I share a coaching conversation I had with an ops professional moving toward data analysis who calls his interview narrative “spin,” and reframed it as honest conviction and initiative rather than performance, linking this to Covey’s first “wave” of trust: self-trust as the foundation for relationship and organizational trust. I also critique companies spinning layoffs as AI-driven when they often reflect pandemic overhiring, warning that spin breeds cynicism and slows real adoption.

00:00 The Big Idea
00:55 Trust as Economic Force
01:50 Coaching Story Spin vs Reframe
04:49 Self Trust Comes First
05:40 Layoffs and the AI Narrative
07:29 Low Trust Tax at Work
08:36 Five Waves of Trust
10:31 Culture Leaks to Customers
11:49 Conviction Over Certainty
12:37 Closing and How to Reach Me

Empathy at Scale: James Warren on Building SEEQ, Trust, and the Emotional Data Behind Work

This week, we continue our conversation with James Warren, who left a successful corporate career and built Share More Stories (SMS) alongside an investor/partner through a decade-long, sometimes exhausting dual-company arrangement that required relinquishing control, building trust, and personal growth. James explains SMS’s evolution from storytelling workshops into SEEQ, a productized platform that captures employee and customer stories and analyzes emotions to reveal the “why” behind metrics like NPS and engagement scores. After launching in late 2022, the company faced market re-education in 2023, gained momentum in 2024, and is now scaling with added generative-AI capabilities such as SEEQ GPT for rapid, high-context analysis. He describes how leaders must model healthy vulnerability, and shares a case where employee and customer trust curves mirrored, linking employee experience to customer experience. The host closes by reflecting on SEEQ as infrastructure for measuring an organization’s emotional layer.

00:00 Part Two Setup
01:40 Arranged Marriage Partnership
02:56 Letting Go Of Control
06:25 Two Businesses One Gearshift
07:43 Startup Hiring Build Mode
08:53 Going Full Time SMS
10:03 Being Early In Market
11:05 SMS Origins And Pivots
12:45 Workshops To Tech Breakthrough
15:06 First Big Pitch And API Demo
18:49 Launching SEEQ And Reeducation
23:29 Empathy At Scale Value
26:08 What Stories Reveal At Work
29:11 Psychological Safety Signals
30:05 Facilitating Live Storytelling
30:49 The Magic Moment
32:39 Leaders Embrace Vulnerability
35:18 Asking Better Questions
37:03 Selling Employee Experience Value
40:41 Trust Links EX and CX
45:01 Emotional Archeology
47:06 SEEQ GPT Breakthrough
53:56 Advice For Feeling Stuck
57:26 Trust Reflection Outro

We kick off Season 2 of the Push-Pull Podcast, we widen the lens from career transitions to how people build durable careers amid rapid change. In this episode, I interview James Warren, founder and CEO of Share More Stories, who is a storyteller committed to helping organizations understand their employees’ and customers’ experiences. James recounts early storytelling and entrepreneurial interests, studying at Princeton before transferring to Columbia for creative writing, and learning persistence through rigorous workshops. After marrying young, he entered corporate roles at MetLife and then Altria, where self-advocacy and mentorship fueled moves from communications to brand/marketing to sales, revealing shifting generational expectations about “job hopping.” He eventually left Altria with a package to pursue entrepreneurship, describing a difficult first year, early failed ventures and a failed crowdfunding campaign, and a pivotal partnership that provided the material and experiential resources to build Share More Stories.

00:00 Season Two Mission
00:50 Building Durable Careers
02:24 Meet James Warren
04:19 James Today Snapshot
05:14 Early Storytelling Roots
07:41 Writing Path to Columbia
09:59 Pressure Intuition Pivots
15:07 First Corporate Breaks
18:48 Altria Growth and Moves
23:52 Jump to Brand and Sales
29:53 Sales Role Reality Check
31:50 Resentment In The Field
32:26 Work With Lunch Lesson
33:42 Reorgs And Returning HQ
35:40 Choosing To Leave Corporate
37:19 First Year Entrepreneur Reality
39:36 Origins Of Share More Stories
45:32 Crowdfunding Failure Wakeup
47:31 Mentors And Finding Ken
51:48 Partner Deal And New Runway
53:10 Host Reflection And Wrap

Announcing Season 2 of the Push Pull Podcast. In the world of rapidly evolving AI tools, and the expectations and market disruptions that come with them, ignore the losers trying to scare you. Find what matters to you and be the champion of your own story.

The past few weeks I soft-launched a hiatus, and today I'm making it official. Keep your eyes peeled for Season 2 of the Push Pull Podcast!

Today we revisit a couple of “near misses” — where a combination of solid preparation and luck led my guests to thrive or pivot quickly in the face of turmoil in their organizations.

Omar Dinar discusses joining Lehman at the onset of the financial crisis, and the impact of the bank's bankruptcy on his career. Being in the real estate division allowed him participation in the acquisition negotiations by Barclays where he excelled for a solid portion of his career.

We then revisit our discussion with Annalyn Cruz, at the point where she had years of advising university students under her belt. At a crossroads, she made the tough call to take a pay cut to go into Learning and Development when she had the option to move to a Director-level role. This choice didn’t save her from impending layoffs, but future-proofed her resume to work in corporate spaces.

00:00 Introduction to the MBA Journey
00:25 Landing the Dream Job at Lehman Brothers
02:04 The Financial Crisis Unfolds
02:57 Experiencing Lehman's Collapse
08:07 Transition to Barclays
08:32 A New Path: Semester at Sea
09:49 Pivot to Learning and Development
12:04 Challenges and Growth in L&D
18:03 Final Reflections and Career Transition