Episode 411
AI failure rates shock me.
Erin Gajdalo, CEO of Pluralsight, joined me and what she revealed about why AI projects collapse disturbed me even more..
I expected to talk about tools, frameworks, and roadmaps.
Instead, Erin asked me question I wasn’t ready for:
“Is your team actually ready for this? How can you even tell?"
Um...
Because most leaders — myself included — push for AI adoption without slowing down to ask if our teams can actually absorb the shift.
Erin has led major transformations at Avantax, LPL, and now Pluralsight... and she’s seen the same silent pattern across industries:
Leaders blame the tech.
Teams blame the workload.
But the real problem is almost always hidden deeper.
Readiness....and getting their quickly....is everything.
In our conversation, she breaks down:
👉 The blind spot most CEOs overlook.
👉 Why 50% of AI projects fail.
👉 What separates teams that finish from those that stall.
👉 The first move every CEO should take when they realize their team can’t keep up.
👉 And how her transformation background gives her a unique advantage in the AI era.
This conversation changed the way I think about leading through AI.
What’s the biggest AI readiness challenge you’re seeing in your teams right now?
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Published on 3 days, 8 hours ago
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