Pro Tips for Corporations Looking to Upskill with AI

Corporate leaders, let’s level set for a minute.

Canada has roughly 21 million people in the workforce today. Every single one of them will need to upgrade their AI literacy—from basic awareness to advanced, role-specific fluency.

This includes both technical professionals (who need to learn how to apply their skills in a business and product strategy context) and non-technical professionals (who need the bridge to understand and lead confidently in AI-driven conversations).

That’s the challenge in front of us: moving everyone—technical and non-technical—together as a unit into the future of work.

And here’s the playbook.

Too many companies are still treating AI training like a team-building activity.
A nice-to-have. An afternoon away from the office. Maybe even something “fun” to check a box.

Stop it.

This is not entertainment.
This is not trust-falls with ChatGPT.

Your business is going to war with its future right now.
If you miss this moment, you’re not just behind—you’re out.

1. Stop With the Team-Building Mentality

AI training ≠ a feel-good offsite.
If you’re running it like ropes courses and icebreakers, you’ve already missed the point.

This is about equipping your people with the tools to defend your market position and launch the next generation of products.

Treat it like survival training. Because it is.

2. Know the Real Cost

On average, it will cost you between $2,500 and $6,500 per person to meaningfully upskill your team.

That number shifts depending on role and industry context. But it’s the budget reality you need to start planning for.

If you think you’re going to check this box with a $199 online course, you’re already behind.

3. Train People Where They Work

The most effective AI training doesn’t happen in boardrooms.

It happens at employees’ desks, on their equipment, inside the context where they already work.

That’s where the breakthroughs happen—when they wrestle with their own workflows, files, and constraints.

Smart companies already know this.
Take Walmart, for example. They’ve built self-directed online learning portals that let employees opt in to training that fits their schedule and role. No classrooms. No wasted time.

And here’s the kicker: when employees self-select into training, you learn something powerful—who’s willing to invest in their own growth.

👉 Pro Tip: Track who’s opting in. Those are the people you should be promoting right now. They’re already showing the initiative your future depends on.

4. Build Capacity First

The #1 excuse I hear every day?

“Christa, my people don’t have time for this. It’s such a struggle to get folks to carve out the time.”

Here’s the hard truth: everyone will have plenty of time for training when they don’t have jobs because the company didn’t adapt. You need to intervene on that classic old playbook pushback.

That’s why our model uses the first two sessions for capacity-building. We show employees how to use AI to buy back 3+ hours in their work week.

Guess what? Now they have time for training.

And here’s the kicker:
If you don’t think your teams can spare 90 minutes a week online to learn, you’re the company that needs this the most.

Because if your people are that maxed out, you’re already in trouble. Those early capacity-building wins are exactly what will reorient your company toward where it actually needs to go.

5. This Is About Survival, Not Fun

Your competitors are embedding AI into products, workflows, and customer experiences.

If you’re still treating AI as a fun side project or “innovation theatre,” you’re already behind.

This is not about “learning AI.” It’s about embedding AI into the core of how your business operates.

6. If Your Training Isn’t Structured This Way, You’re Already Wasting Your First Attempt

Half-day workshops won’t save your business.

You need a structured, contextual, and capacity-driven approach:

• At-desk learning with real workflows

• Industry-context applications

• Capacity building first to free up time

• Strategic fluency to drive products and decisions

If you’re not doing it this way, you’re setting yourself up to spend twice the money and twice the time on a “second attempt.” And by then, your competitors may have already pulled ahead.

The Bottom Line

This isn’t team-building.
This isn’t optional.
This isn’t about “someday.”

This is about whether your company will be here in five years.

So stop looking for entertainment. Stop pulling people out of context. Stop pretending you don’t have time.

Train your people where they work. Build capacity first. Invest in the future.

And here’s the irony: if it’s done well, with human-first educators like us, everyone comes out the other side unified, excited, and hopeful about their future.

We’ll call that the team builder bonus you get for free.

Want to talk about what this can look like? Come find us. We’ll show you the way.

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