The Best-Laid Plans
I had it all figured out.
Ten minutes to download Whisper Flow. Maybe fifteen if someone needed to find their password. Then we'd move on to the real training—the exciting stuff about voice-to-text and capturing ideas on the fly.
I even had a second item on the agenda. A self-assessment survey about AI readiness. Very organized. Very professional.
I was feeling pretty good about myself, honestly.
The First Five Minutes
"Okay everyone, let's go to the Whisper Flow website and click Download."
Simple, right? The kind of instruction that requires no explanation. Like "open your email" or "click the blue button."
Except.
Some people couldn't find the download link. Some people found it but got a security warning. Some people got the file but it sat in their Downloads folder doing nothing. Some people double-clicked and... nothing happened.
And then there were the installation screens. The permissions prompts. The "allow access to microphone" dialogs that nobody was sure they should click "yes" on.
The Hour That Wasn't Supposed to Happen
Ten minutes became twenty. Twenty became forty. Forty became... an hour.
An hour of "where did it go?" and "mine says something different" and "I think I need to restart my computer?"
An hour of me asking people to share their screens on Teams, squinting at error messages I'd never seen before, trying to troubleshoot remotely while everyone watched.
An hour that was supposed to be the easy part.
The Thing Nobody Tells You
Here's what I've learned from teaching AI tools to real people in real workplaces:
We talk about AI like it's the future. Cutting edge. 21st century.
But the laptops we're running it on? They've got their own opinions about the future.
Corporate laptops have security policies. Download restrictions. Admin permissions that require IT tickets and possibly a small sacrifice to the technology gods. What should be "click and go" becomes "click and wait and troubleshoot and maybe try again tomorrow."
This isn't a failure of the people trying to learn. It's the reality of enterprise environments.
The AI is ready for the 21st century. The infrastructure isn't always there yet.
What Felt Like Failure
I'm not going to pretend that session felt like a win.
I had planned a training about using AI. Instead, we spent an hour on a Teams call proving that accessing AI is still harder than it should be.
People were frustrated. Some probably wondered why they'd blocked off their calendar for this. I could feel the energy shifting from "this is exciting" to "this is annoying"—even through the video call.
And honestly? I felt it too.
What Saved the Day (Sort Of)
Here's where having a backup plan paid off.
My second agenda item was a simple self-assessment: How do you feel about AI? What are you curious about? What worries you?
We pivoted to that. And suddenly, the energy shifted again.
Because even though people couldn't run the tool yet, they could still talk about it. They could share their questions, their hopes, their concerns. They could start thinking about how AI might actually fit into their work.
It wasn't the session I planned. But it was still a session.
The Path Forward
I'm scheduling one-on-one meetings now.
Fifteen minutes with each colleague. Just enough time to share screens, troubleshoot their specific laptop situation, and get them actually set up.
What should have been a ten-minute group activity is now a series of individual appointments. That's not efficient. That's not scalable. That's not what the AI evangelists promised when they said "anyone can do this."
But it's real. And real is what my colleagues need.
The Lesson I Keep Learning
This isn't the first time I've watched a "simple" setup turn into an hours-long adventure. And it won't be the last.
The hardest part of AI isn't understanding prompts or learning new workflows or figuring out what to automate.
The hardest part is the first five minutes.
The download. The install. The permissions. The "why isn't this working?" moment that makes people feel like they're already behind before they've even started.
If you're trying to bring AI to your team, your coworkers, your organization—budget for this. Plan for it. Expect that "quick setup" will take three times as long as you think.
And when it does? Don't let anyone feel like they failed.
They didn't fail. The gap between "AI is easy" and "your corporate laptop has other ideas" isn't their fault.
Your Turn
If you've ever tried to teach someone a new tool and watched a "ten-minute task" turn into an hour of troubleshooting—you're not alone.
This is the messy, frustrating, very human reality of technology adoption.
It's not as exciting as the demos. It's not as smooth as the tutorials.
But it's where real change actually happens: one stubborn download at a time.
Still scheduling those one-on-ones, still believing the setup struggle is worth it, still reminding myself that patience is part of the process.
P.S. To everyone who sat through that hour with me and didn't give up: Thank you. As a small token of appreciation for your patience, I sent you all Focus Logger—another tool I think you'll love once we get past the download. We'll get there. And when we do, you'll forget how hard this part was. I promise.
P.P.S. If anyone figures out how to make corporate IT policies and cutting-edge AI play nicely together, please let me know. I have colleagues waiting.