The Identity Crisis Nobody's Naming, with Annie Tsai

Annie Tsai is Chief Operating Officer at marketing technology company Interact, where she has spent 25 years building, growing, and scaling software companies. She also serves as COO of Moms in Tech, a global community of over 19,000 working mothers in the industry, and writes two weekly columns on technology and AI. Before this, she spent more than fifteen years leading customer experience and cross-functional teams from the C-suite.In our conversation, we discuss:Why the shift from orchestrating work to actually executing it herself is creating a very real identity crisis, and not just for junior workersThe real cost of running twenty concurrent strategic initiatives without gaining any personal capacity, and the systems she had to build, then open source, just to keep track of it allWhat she had to let go of to get here: the clout that comes with a title, and the belief that time served still earns you anythingWhy taste and craft, not raw skill, is what separates someone with institutional knowledge from a new grad using the same AI toolsWhy almost nobody in a room full of early AI adopters knew what "planning mode" was, and what that reveals about how most people are still using AI wrongWhy she thinks this identity crisis might finally break America's habit of letting work define who we areWhere to find Annie:Personal: annietsai.comomsintech.comWhere to find Vlad:Website: vladmoskovski.comLinkedIn: linkedin.com/in/vladmoskovskiFree Somatic Intelligence Toolkit for LeadersAI gives everyone data. The leaders who stand out also listen to their body's intelligence. Download the free toolkit here: vladmoskovski.com/handbook-landing-pageTimestamps:00:00 Introduction, and why work now means holding twenty conversations at once that never end00:58 Who Annie Tsai is: COO at Interact, Moms in Tech, and her upcoming third book02:44 The premise behind her column: a generation trained to become one expert thing, now disrupted04:27 From orchestrator to executor: how her actual role changed over the last few years08:21 The cognitive cost of running twenty strategic initiatives at once, and the systems she built to survive it10:43 What she had to let go of: the clout that comes with a title12:20 Taste and institutional knowledge as the real differentiator AI can't replace17:15 Her hope for the American workforce: that what we do stops being who we are18:24 The grief of losing a skill you used to love, and why it deserves to be named as grief20:47 Painting murals, and finding the time to fill the buckets that make you feel like yourself21:55 Advice to her thirteen year old son on what to study and why25:10 Creativity as the new white picket fence29:58 Metacognition as the most underrated AI skill, and why almost nobody in the room knew what planning mode was32:32 Why "AI native" is the wrong hire, and what to look for instead35:35 Modeling AI use as a leader, and the CEO who built the dashboard instead of just talking about it36:30 Closing: what people will be pleasantly surprised to evolve into