Why Informal Learning Can’t Be Ignored episode artwork

EPISODE · Jan 22, 2026 · 53 MIN

Why Informal Learning Can’t Be Ignored

from Harald’s Curious Corner · host Harald Overaa

“How do we drive real skills transformation within a company?”That’s the question we explore in this episode with Eran Vaisfailr, former Product Owner of Learning and Development at Booking.com, now Co-founder and CEO of Plynn, a learning startup focused on turning informal learning into measurable skills. In his time at Booking.com, Eran was at the forefront of building a skills-based organisation, focusing on aligning employee capabilities with business needs.Our conversation explores why skills-based transformation isn't just about formal training systems or shiny new AI tools. Eran shares his experience at Booking.com, where skills intelligence was key. He highlights how day-to-day work, projects, and even platforms like YouTube often offer more valuable learning insights than LMS completion rates.If you’re feeling the pressure of complex skills frameworks and a widening gap between training and performance, this episode offers a grounded roadmap for L&D’s evolution in the age of AI.Some curious takeaways:Skills transformations fail when data foundations aren’t clean and alignedMeasuring performance improvement is the true test of a skills programme’s successStart skills work where the business feels the pain, not everywhere at onceEpisode highlights:(00:00) Welcome to Harald’s Curious Corner(04:26) The biggest mistakes organisations make when implementing LMSs(10:12) Consolidating learning data in complex organisations(12:45) Why Booking.com invested in a skills-based organisation(15:06) Skills only matter when you can prove them(20:04) The hidden data challenges behind skills verification(23:36) Working with business leaders on skills change(28:33) The real reason skills data never lines up(32:32) Why one-size-fits-all learning keeps failing(37:37) Turning YouTube into structured, trackable learning(42:56) Why L&D can’t own just-in-time learning alone(50:03) Reducing system overload and designing learning where work happens(52:21) Curious Corner TakeawaysConnect with the guests:Eran Vaisfailr on LinkedIn: https://www.linkedin.com/in/eran-vaisfailr/ Explore Plynn: https://www.plynn.dev/ Follow me on the following sites:Harald Overaa on LinkedIn: https://www.linkedin.com/in/haraldovera/ Subscribe to Harald’s Newsletter: https://www.linkedin.com/newsletters/6901795950403186688/ 

“How do we drive real skills transformation within a company?”That’s the question we explore in this episode with Eran Vaisfailr, former Product Owner of Learning and Development at Booking.com, now Co-founder and CEO of Plynn, a learning startup focused on turning informal learning into measurable skills. In his time at Booking.com, Eran was at the forefront of building a skills-based organisation, focusing on aligning employee capabilities with business needs.Our conversation explores why skills-based transformation isn't just about formal training systems or shiny new AI tools. Eran shares his experience at Booking.com, where skills intelligence was key. He highlights how day-to-day work, projects, and even platforms like YouTube often offer more valuable learning insights than LMS completion rates.If you’re feeling the pressure of complex skills frameworks and a widening gap between training and performance, this episode offers a grounded roadmap for L&D’s evolution in the age of AI.Some curious takeaways:Skills transformations fail when data foundations aren’t clean and alignedMeasuring performance improvement is the true test of a skills programme’s successStart skills work where the business feels the pain, not everywhere at onceEpisode highlights:(00:00) Welcome to Harald’s Curious Corner(04:26) The biggest mistakes organisations make when implementing LMSs(10:12) Consolidating learning data in complex organisations(12:45) Why Booking.com invested in a skills-based organisation(15:06) Skills only matter when you can prove them(20:04) The hidden data challenges behind skills verification(23:36) Working with business leaders on skills change(28:33) The real reason skills data never lines up(32:32) Why one-size-fits-all learning keeps failing(37:37) Turning YouTube into structured, trackable learning(42:56) Why L&D can’t own just-in-time learning alone(50:03) Reducing system overload and designing learning where work happens(52:21) Curious Corner TakeawaysConnect with the guests:Eran Vaisfailr on LinkedIn: https://www.linkedin.com/in/eran-vaisfailr/ Explore Plynn: https://www.plynn.dev/ Follow me on the following sites:Harald Overaa on LinkedIn: https://www.linkedin.com/in/haraldovera/ Subscribe to Harald’s Newsletter: https://www.linkedin.com/newsletters/6901795950403186688/

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Why Informal Learning Can’t Be Ignored

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This episode was published on January 22, 2026.

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“How do we drive real skills transformation within a company?”That’s the question we explore in this episode with Eran Vaisfailr, former Product Owner of Learning and Development at Booking.com, now Co-founder and CEO of Plynn, a learning startup...

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