Empowering Teams with AI Training

Author

Charlene Li
August 11, 2025

"We’re going to become an AI-first company."

When CEOs make this kind of declaration, they might be expecting excitement, new innovations, or a surge of inspired productivity. 

Instead, most teams panic. 

A recent study reveals a troubling reality: there's a massive gap between executive expectations and employee readiness. Leaders are mandating AI adoption while leaving their teams without the support they need to succeed.

The disconnect caused by a lack of appropriate training makes sense. We're asking people to embrace transformative technology while simultaneously abandoning them in the learning process. 

The results are predictable: widespread anxiety, productivity theater, and teams caught between expectations and reality.

The Hidden Cost of Poor Implementation 

The disconnect between leadership intentions and employee reality creates a cascade of problems:

🤷 Most accept AI outputs without proper verification

🫣 Nearly half of employees hide their AI usage out of fear

🤔 People feel pressured to use tools they don't understand

🕜 Workers spend as much time learning and overseeing AI as completing tasks manually

Many workers that use unsanctioned AI are afraid to admit it, while on the other side, workers forced to use AI often opt out and tell their bosses that they’re using it when they’re not. This is inefficient at best, and dangerous at worst. When people can't be honest about the tools they're using, you lose visibility into what's actually happening in your organization.

This isn't just about technology adoption. This is about trust, psychological safety, and the fundamental relationship between leaders and their teams.

The Training Dilemma

I keep hearing the same question from leaders: "How do you do AI training when everything is changing all the time?"

It's a fair question. Traditional training models assume stability. You create a curriculum, roll it out, and expect it to remain relevant for months or years. AI development moves too fast for these traditional models, and that's exactly why leaders need to rethink the way they approach training entirely.

The Solution: Hybrid Learning That Actually Works

The answer lies in a flexible approach. Formal training and freeform experimentation work well in tandem when it comes to AI training, because it gives workers a solid foundation while also empowering them to adapt alongside the technology. 

Centralized Training: Your Starting Point

Some things need to be consistent, comprehensive, and carefully controlled:

🔹 Company policies: What's allowed and what isn't

🔹 Universal best practices: Baseline skills everyone needs

🔹 Safety and ethics protocols: How to identify risks and biases

🔹 Critical thinking frameworks: How to verify and validate AI outputs

Think of centralized training as building the guardrails. It's slower to develop and deploy, but it creates the psychological safety people need to experiment confidently.

Decentralized Learning: Your Acceleration Engine

The real magic happens in the informal, peer-to-peer learning that responds to real challenges in the context of real work, in real time:

🔹 Sharing sessions discussing wins and failures

🔹 Cross-functional showcases of creative applications

🔹 AI office hours where colleagues troubleshoot together

🔹 Experimentation challenges that encourage innovation

Beyond just learning how to use AI tools, AI training is about developing curiosity, imagination, critical thinking, and adaptability. 

The goal is to create an environment where people feel supported in making the inevitable mistakes that come with mastering new tools.

Making This Real

Start by asking yourself: What are your people really afraid of?

Is it the technology itself? Or is it the fear of looking incompetent, making mistakes, or being replaced?

Address the human elements first. Create spaces for honest conversation about AI concerns. One organization created an intro to AI course specifically for people who are more skeptical about AI so that there is time to properly address areas of concern. 

Then build your hybrid approach:

➡️ Celebrate both successes and intelligent failures

➡️ Establish your non-negotiables through formal training

➡️ Create multiple informal learning opportunities each week

➡️ Make it clear that curiosity and experimentation are job requirements

Your Turn: 

How is your organization handling AI training? Are you seeing signs of AI anxiety on your team?

I'd love to hear what's working (and what’s not!) as you navigate this challenge.

What I Can’t Stop Talking About

  • What part of your job do you want AI to take? As the reality of work changes with AI, workers are shifting focus from “will I be replaced” to questions about how to work alongside AI.

  • Authentic leadership is more important than ever, especially in the age of AI. Listen to my conversation with Jerry Won on his podcast Tomorrowist to learn how leaders can step up in this crucial moment.

My Upcoming Appearances/Travel

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