Issue #07 · July 2026

How Learning to Use AI at Work Reveals
How You Actually Do Your Job

I see business owners come to AI the same way over and over: they expect it to do their job right out of the box. When it doesn't, they decide AI is overhyped and go back to what they were doing.

That disappointment usually isn't an AI problem. It's a mirror reflection of the person using AI. Learning to use AI at work is a skill, and almost nobody tells you what building that skill actually reveals.

The Reason AI Disappoints Most People

When we work with clients on AI adoption, we notice the same pattern. Someone wants AI to take over a task they do every day. So we ask them to describe how they do it. And more often than not, they can't. Not because they're not good at it. Quite the opposite. They're so good at it that the whole process lives in their head and runs on autopilot.

So think about the conundrum here. If you can't describe how you do the work, how can you expect AI to do it for you? This is the same trap behind one of the most common questions business owners are asking right now: "I started with the tool and I'm trying to work backwards to the problem. Is that wrong?"

The instinct makes sense, but it's backwards. You can't teach AI to do a process you've never actually described.

Teaching AI Is the Real Skill

The conversation online is stuck on prompting. Prompt libraries, prompt courses, the 10 prompts that will change your niche. Prompting is real, but it's not the point.

The actual skill is teaching. When you learn to teach AI to work with you and for you, you're doing the same thing you'd do with a new hire: naming the steps, explaining the judgment calls, and defining what "good" looks like.

That's where the value hides. The moment you slow down to teach AI how you work, you're forced to look at your own process through a different lens.

The Two Bonus Wins That Outlast Any Tool

Learning to use AI at work produces two branched-off benefits that outlast any single tool.

A better understanding of your own work. When you describe a task step by step, you see what actually works, what doesn't, and which steps were just fluff. Redundancies. Steps to fix a problem that no longer exists. Teaching AI is a review of your workflow that you didn't sign up for but desperately needed.

A clear view of where AI fits in your role. Not the doomer version where it replaces you, and not the regret version where it does nothing useful. You start to see which parts of your job are repetitive and rule-based, which parts need your judgment, and where AI can genuinely carry the load.

This is why so many companies are stuck in what researchers call "pilot purgatory." Three-quarters of companies that start experimenting with AI struggle to move past the experimentation stage. They ran a test, it underwhelmed, and they stalled. In most cases they skipped the part where you learn to teach the tool what your work actually involves.

How to Start Using AI at Work the Right Way

If you've tried AI and it let you down, or you don't know where to start, here's a simple first step.

Pick one task you do regularly. Before you open any AI tool, write down every step of how you do it, as if you were training someone who has never seen your business. Where do you start? What do you check? How do you know it's done? You'll likely find you can't finish in one sitting, and that gap is exactly where you didn't understand your own process as well as you thought.

Then bring in the AI and teach it what you wrote.

Working with AI is a skill that has to be built. The businesses pulling ahead aren't the ones with the fanciest tools. They're the ones willing to describe how they actually work, spot the gaps, and put AI where it belongs.

Execute. Rinse. Repeat.

Want the full version of this idea, including the exact first step I'd have you take? Read the complete breakdown in this week's newsletter.

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Frequently asked questions

Why does AI disappoint so many people at work?

Most people expect AI to do their job right out of the box. But the work they want to hand over lives in their head and runs on autopilot, so they can't describe it. If you can't describe how you do the work, you can't expect AI to do it for you.

Is prompting the most important skill for using AI at work?

No. Prompting is real, but the actual skill is teaching. When you teach AI to work with you, you do the same thing you'd do with a new hire: name the steps, explain the judgment calls, and define what "good" looks like.

What is pilot purgatory and why do companies get stuck in it?

Pilot purgatory is when a company experiments with AI, gets underwhelming results, and stalls. Roughly three-quarters of companies that start experimenting with AI struggle to move past this stage, usually because they skipped teaching the tool what their work actually involves.

How do I start using AI at work the right way?

Pick one task you do regularly. Before opening any AI tool, write down every step of how you do it, as if training someone who has never seen your business. Then bring in the AI and teach it what you wrote.

What do you gain from teaching AI how you work?

Two things that outlast any tool: a better understanding of your own work, because describing a task step by step exposes redundant steps, and a clear view of where AI fits in your role, from rule-based work AI can carry to the judgment calls that stay yours.