🗝️ This fear slowed me down for 20 years
"The best way to find out if you can trust somebody is to trust them." — Ernest Hemingway
🔑 This issue at a glance (2-second summary)
Some tasks you've refused to delegate aren't about the task. They're about the risk of the person. AI takes that risk off the table.
The travel mistake that scarred me
Twenty years ago, I worked with a pretty well-known client. One day, his human executive assistant got his travel wrong and left him stranded on the tarmac. Because of that, he missed a big opportunity. He was livid, and he fired her over it.
She didn't mean to do it. It was human error. But she was gone.
I was young, and it stuck with me. I told myself right then, I'll delegate a lot of things in my business, but not travel. Travel I'll always book myself.
So that's what I did for twenty years. Every flight, every hotel, every car...I booked them myself. I travel a lot, and that was easily an hour of time and mental calories burned for each trip.
Until a few weeks ago.
I started training Henley, my A.I. executive assistant, to book my travel. Now it's flawless.
Once a speaking engagement is confirmed, Henley reads the contract. He knows the city, the venue, the start and end time. He books the flights around it using my preferences. He books the hotel using my loyalty numbers and my rules about distance from the venue. He even schedules my rideshares in advance.
Monica walked into my office the other day and saw Henley's screen moving on its own. She said, "What is he doing?" He was booking my Ubers.
I still book my personal travel, the family vacations and the fun stuff. But routine travel, the speaking engagements and client trips with a clear start and end time, Henley owns that now. Twenty years of that particular knot in my chest, gone.
My fear was never about the travel. It was about trusting a human with something that could leave me stranded. Humans have bad days. We forget. We rush. We miss the fine print. An A.I. employee doesn't. Henley runs the same play with the same care every single time.
You have your own version of my travel. The task you refuse to delegate. The report you still pull yourself at midnight because someone botched it once. The invoice you still cut by hand because a person billed the wrong client years ago and you never forgot it.
That's the task an A.I. employee should own next. And you hand it off the same way I handed off Henley: through conversation.
Winners take action
Pick the task you've been carrying alone for years, then talk it out loud until it becomes a skill file.
A skill file is just a plain-English document your A.I. reads to know how to do a task, like an SOP you'd hand a new hire, except your A.I. writes it and keeps it current for you. This is how I trained Henley on my travel. Not by typing out a document myself. By having a conversation. I told him my preferences, my thresholds, my gotchas, the same way I'd brief a new assistant on their first day. Every correction I gave became part of that skill file, and it's the whole game.
Here's your move this week:
Open your main A.I. tool, turn on your microphone, and walk it through your one guarded task out loud. The airline you default to. The price ceiling. The hotel rule. The exception you always make. Don't hold back the small stuff, because the small stuff is the value.
Then tell it "turn everything I just said into a skill file that you follow every time, and keep updating that file whenever I give you corrections, so I never have to repeat myself twice. Do you understand?"
Let it run the task once while you watch. Correct what it misses. Watch the skill file get sharper.
Do that for a couple of weeks, and you'll trust it the way I now trust Henley. He books me into hotels I never even look up before I land.
The tools you need
Talking out a skill file works great. But some tasks are easier to show than to say. For those, let the A.I. watch you do it.
Challenge: Some training needs visuals. Those tasks that have too many clicks, tabs, and tiny judgment calls to narrate cleanly. You'd spend an hour describing it and still leave things out.
Solution: Record your screen while you do the task once. The A.I. watches the whole thing, hears you talk through it, and writes the skill file for you. Then it can repeat what you did.
Try this in 10 minutes:
In Claude, click over to the Cowork side, click the + button, and use the "Record a skill" feature. In ChatGPT, the same thing lives under the record-and-replay plugin, or you can turn on Computer Use in settings and let it watch your entire screen while you work.
Hit record and do the task once, start to finish, the way you always do it. Open the app, log in, run the report, whatever it is. This works great for legacy software that has no API to connect to, because the A.I. just watches you use it like a human would.
Talk out loud the whole time. Say what you're clicking and why. The A.I. reads the transcript alongside the screen, so your narration is what turns a recording into real understanding.
Stop the recording. It generates a long skill file that captures the exact process. Save it, name it, and now any of your agents can run that task.
This is how you hand off the messy stuff that never fit into a written SOP. Start with a small task. Show it once, and your A.I. employee has it forever. You just keep refining it over time. That is the difference between a chatbot that answers questions and an employee that does the work.
This week on the pod
This week on King Moves (What Would You Delegate to AI, But Not a Human? | Ep. 148), Justin and I trade some use cases that made us stop and ponder. His assistant Edgar caught something on Justin's calendar that Justin never asked him to look for. You'll want to hear what it did next.
We also get into how we named our agents. Fun fact: turns out I'm actually a descendant of Claude. You'll have to listen to find out what I mean by that.
And we go a few rounds on why the "silly" personal use cases might be the most valuable ones of all.
If you've been sitting on a task you refuse to delegate, start here.
Listen on Apple Podcasts
Listen on Spotify
Listen on YouTube
Watch on YouTube
Stop playing life on hard mode. Automate your success.
Until next week,
Ethan King
A.I. Automation for Business Growth
Keynote Speaker | Author | CEO | Strategist
P.S. On Sunday, September 28, I'm running Build My AI Team Live, where I walk you through building your own AI employees in real time. Not theory. You build alongside me. Spots are limited and the waitlist is open now: buildmyaiteam.live
P.P.S. Here's where I'll be speaking and working with teams over the next couple of months. If you'll be at one of these, come say hello. And if your team could use hands-on help putting AI to work, let's talk.
September 15: EO Southwest Ontario. AI Beyond the Hype Part II: Build Your Digital Dream Team
September 17: EO Boston. AI Beyond the Hype, Part II (during Prompts and Circumstance: AI Keynotes + Show-and-Tell)
September 23: Atlanta Founders Forum. AI Beyond the Hype, Part 1: Turn AI into ROI
September 24: Private logistics technology company. Full-day AI training in the Sacramento area
September 28: Build My AI Team Live. I walk you through building your own AI employees in real time (join the waitlist)
October 2: Private construction company. On-site AI employee build in South Florida
October 7: EO Tulsa. AI Beyond the Hype: Part 1, Turn AI into ROI
October 8: EO Oklahoma City. AI Beyond the Hype: Part 1, Turn AI into ROI
October 20: EO Fort Worth. AI Beyond the Hype Part II: Build Your Digital Dream Team
October 29: EO New Jersey. AI Beyond the Hype Part II: Build Your Digital Dream Team That Works While You Sleep
• • •
New to this newsletter? Grab past issues here.
Note: This newsletter may contain affiliate links. If you choose to purchase after clicking a link, I may receive a commission at no extra cost to you. However, please note that I only share products I actually use myself and believe in.
