Lidia Oshlyansk reflects on navigating decades of tech evolution - from webmaster days to AI - and shares tactical advice for product operatives. Drawing parallels between today’s AI boom and past shifts (web/mobile revolutions), we talk about transferable skills (negotiation, systems thinking) over fleeting tools, debunks "future-proofing," and advocates curiosity-driven adaptability.

Key Timestamps

01:58 - Lidia’s unconventional path: From "business architect" to CPO roles at Spotify/Google
04:07 - Case Study: How "information architects" evolved into modern UX strategists
08:51 - Reality Check: "GPT-5 won’t fix human-centered leadership" (critical systems thinking)
14:21 - Data Point: 27 COBOL developer jobs in Sweden today (adaptation > prediction)
20:21 - Framework: Transferable skills that outlast tools (with PM/UX examples)
27:46 - Leadership Hack: Building "future-proof" teams through skill adjacency mapping
34:39 - Candid Talk: Why existential crises plague tech leaders (and how to reframe them)
42:02 - Tactical Takeaway: "Block 30 min/week for AI upskilling – no agenda required"
50:26 - Counterintuitive: "Stop future-proofing careers – start curiosity-proofing"

3 Strategic Themes for GTM Leaders

Navigating AI Disruption
- Why AI adoption curves mirror mobile/web revolutions1
- The critical human skills that remain automation-resistant (e.g., negotiation, prioritization)
Building Resilient Teams
- Identifying "evergreen" skills (e.g., information architecture → modern UX strategy)1
- Creating psychological safety for continuous reskilling
Personal Adaptation Playbook
- Curated peer learning networks > generic upskilling platforms
- Career capital vs. career comfort tradeoffs

Quotes

"Your ability to negotiate priorities with engineers/designers/execs is the ultimate transferable skill" – Lidia

"We don’t need future-proof careers – we need curiosity-proof humans" – Leah

Guest Background

Current Role: CPO @ Gillian (building the world’s largest growth platform for founders)
Career Highlights:
- Scaled products at Spotify, Google, and Eschew
- PhD in Human-Computer Interaction (early web/UX focus)
- Pioneer in animated GIFs and 1990s web design

Send us a text

Leah on Linkedin / Twitter / Youtube

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