Some interviews stick because they take a noisy topic and bring it back to reality. This was one of them. I spoke with Erin Gajdalo, CEO of Pluralsight, about what it actually takes to upskill a workforce in an AI era that seems to change by the week. We compared boardroom intent with day-to-day practice, and Erin was refreshingly clear about both.

Pluralsight began more than twenty years ago in classrooms, moved online as the market shifted, and now supports Fortune 500 teams with expert-led courses, hands-on labs, and the admin tools leaders need to measure progress at scale. The thread running through the whole story is simple: people learn by doing, and companies get value when that learning maps to real work.

We talked about AI in her own workflow first. Erin uses it to draft presentations, crunch data, and speed up research, then pushes that mindset across the company through focused sprints where every department experiments and reports back. That culture piece matters.

Pluralsight's latest research found that 61 percent of respondents still think using generative AI is "lazy," which drives employees to adopt tools in the shadows and exposes the business to avoidable risk. Her answer is clear guidance, safe environments to practice, and permission to test without fear of failure.

The payoff shows up in real examples. One financial services firm raised prompt engineering efficiency by 20 percent and saved 1,600 hours in three months by pairing assessments with prescriptive learning paths and hands-on practice.

We also explored the fear that keeps people quiet. Layoff headlines travel faster than case studies, and that skews the mood inside many teams. Erin makes a straightforward case. Treat AI as an assistant that improves standard and repetitive tasks, protect the business with clear policies, then invest in education for everyone, not only engineers.

Close the confidence gap with data. Baseline skills, prescribe learning, measure proficiency, and tie improvements to actual tasks. When leaders show their own work and give teams room to try things, adoption follows.

The conversation finished on the future. Technical skills will keep evolving, but the standout advantage will be a willingness to learn and the soft skills that carry ideas from prototype to production.

Erin also shared a personal goal that resonated with me. She would love a private breakfast with Serena Williams to talk about Serena Ventures and backing founders from underrepresented groups. It fit the theme of the episode. Talent is everywhere. Opportunity appears when someone opens a door and stays long enough to help you through it.

If you want the full story, including how Pluralsight is updating its platform for scale and how leaders can reduce "shadow AI" without slowing innovation, you can find their research and resources at Pluralsight.com. 

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