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

1. Navigating AI Disruption
   • Why AI adoption curves mirror mobile/web revolutions1
   • The critical human skills that remain automation-resistant (e.g., negotiation, prioritization)
2. Building Resilient Teams
   • Identifying "evergreen" skills (e.g., information architecture → modern UX strategy)1
   • Creating psychological safety for continuous reskilling
3. 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