What happens when you realize great training isn’t enough?

That’s the question Jess Almlie faced when she left the corporate world to build her own business and began discovering the limits of traditional learning and development. In this conversation, she shares the highs and lows of being self-employed, the lessons behind her new book L&D Order Taker No More, and why too many trainers set themselves up for failure by treating every problem as a “training problem.”

Jess explains how she learned the hard way that even the best-designed programs can fall flat if they’re not addressing the real issue. Misaligned systems, unclear expectations, or poor management habits can’t be fixed by a course or a workshop. Her solution: stop acting like helpers and start showing up as strategic partners. That means slowing down, asking sharper questions, and resisting the urge to plug in training as the default answer.

We also talk about the process of writing a book—how years of blogging, experimenting, and testing ideas gradually turned into a practical handbook that every learning leader wishes they had when moving from order taker to business partner. Jess pulls back the curtain on how she made that transition and what it takes to create lasting impact inside organizations.

If you’ve ever wondered how to stop spinning out content that doesn’t move the needle—or if you’ve thought about writing your own book—this episode will resonate.

Get full access to Lessons from Learning Leaders at lessonsfromlearningleaders.substack.com/subscribe