Issue #19 · Ops & Om · Health of Business series · Episode 3
or listen on Spotify · Apple Podcasts
Everybody tells you the same thing before you hire someone: document your work. So I did. For years. And then the hard part never showed up.
Everything I do is written down somewhere — instructions, project folders, agents that run the work. When I finally brought on a publishing assistant, I was braced for the training.
She was running the work on day one. Not learning the ropes. Running it.
What actually cost me a week was something nobody warned me about, and it had nothing to do with documentation. It was the plumbing.
Documenting your work is not the thing standing between you and getting help. Your infrastructure is.
Here's what we'll cover in this issue:
Why the scary part turned out to be the easy part
What actually cost me a week
The one signal that tells you a hire is working — and it isn't hours
Delegating With AI Agents Is Easy. You Hand Over the System, Not the Task.
The first thing I handed over was show notes for one of the brands I work with — creating them, uploading them, publishing them. I've done that myself for three or four years.
In my head it was going to take a while to explain. It's the kind of thing you only really get once you've watched it happen a few times. It took almost nothing.
I want to be specific about why, because this is the part people get wrong. It wasn't that I'm a good trainer. I didn't hand her a task. I handed her an agent. The thing that does the work already existed. The judgment was already in there — what to pull out, how to frame it, what the format is.
So the handoff wasn't "here's how I think about show notes." It was "here's the system, go run it."
The system is the training. You skip the apprenticeship because there's nothing left to apprentice.
It also does something I didn't expect: it frees her up to be creative without breaking anything. She can look at the order of the steps and ask what if we did this instead — and we both know the system underneath still works.
There was one gap. When show notes move over to YouTube there's a handful of little selections at the end: add the tags, pick a playlist, is there a collaborator, do you want to monetize, did you approve this. I'd been making those on the fly for years and never wrote any of it down. Not because it was hard — because it was invisible. It wasn't a process in my mind. It was just the last step.
That's the honest failure mode of documentation. It isn't the complicated stuff you skip. It's the stuff you never counted as a process at all. I screen-recorded it, turned the recording into an SOP, dropped the SOP into the project folder, and we closed the gap in one session. Maybe 2% of the work.
Try this prompt:
Take the process I just described and turn it into a project agent,
not a checklist. Write standing instructions covering: the goal, the
inputs, the judgment calls you make and the rule behind each one, the
output format, and what "done" looks like. Then list the decisions you
still can't make without asking me — those are the gaps I have to fill.Delegating With AI Agents Breaks on Access, Not Knowledge
To give somebody access to the way I work, I had to move my entire AI setup from a personal account to an organization account. That turned out to be the real project.
You can't just share your login — it gets flagged. And you wouldn't want to anyway. If your assistant is signing in as you, every sign-in somewhere else needs your approval. You become the bottleneck on the exact thing you hired someone to unblock.
Then the parts I didn't see coming:
Project memory doesn't transfer. You can't reach in and move it. I ended up re-feeding the material and re-running it so the new team account could build its own.
Context doesn't copy-paste either. Mine lives inside a project and accumulated over months. You don't rebuild months of accumulation with a click.
Connectors get approved twice. Once at the organization level, then again for each individual person. It's not a bug — it makes complete sense once you see it. But until you do, you're sitting there wondering why it works for you and not for her.
Everything I know how to do was written down. Almost nothing about how I work was set up to be shared.
Two different kinds of readiness — and the whole "document your processes" conversation only covers the first one.
Think about what that means. Every tool you've adopted, every automation you've wired up, every account you've opened, you set up as if exactly one person would ever use it. It works great. It's efficient. And it has a single point of failure standing right in front of you. You don't discover that by writing an SOP. You discover it the first time you try to let somebody else in.
Two things I'd do differently, and I'm already planning for the next move. One: write context and memory out to a doc as you go — it doesn't do that automatically, it keeps everything internal. Two: stop using Google sign-in for everything. It ties the account to your Google, which means your people can't get their own access without going through you.
Try this prompt:
Audit my setup for one-person assumptions. Go tool by tool through the
accounts I use and flag: which ones are tied to a personal sign-in,
which ones can't add a second user without an upgrade, and where my
AI's context or memory lives that wouldn't survive a move. Give me the
list ordered by how badly it would block someone I hired tomorrow.The Signal That a Hire Is Working — And It Isn't Hours
I'm paying for ten hours a week and I'm actively hunting for more to hand her. Third project goes over this week.
I'm not going to give you an hours-saved number, because I'd be making it up. I never did those tasks in their own block of time. They were always smashed in between three other things.
Here's the actual signal. The other day she was working in Shopify for one of my companies and noticed a product we're promoting was low on inventory. She flagged it, and offered an option for what she could do about it. Inventory is nowhere near her lane. I told her no action needed — and then I thanked her, because that's the whole thing.
I've had an assistant before. In all that time, nothing new ever came back. The work got done. Nothing new ever came back.
A pair of hands only ever gives you back exactly what you handed over. The second version is somebody watching the business.
Those two cost about the same. They are not the same thing at all. And I'd push it one step further: you only get the second version if there's something to watch. If it's all locked in your head and your accounts, there's nothing for anyone to notice. Systems aren't just how you delegate. They're the surface area that makes it possible for someone else to see what you missed.
A business that only runs because you're in it isn't an asset. It's a job you can't quit. Most of us who built something on real expertise are somewhere on that line without knowing exactly where — and there's only one way to find out. You let someone in and you watch what breaks.
For me, what broke wasn't the knowledge. It was every assumption I baked in that I'd be the only one standing there. That's fixable. It's just not the work you were told to prepare for.
Try this prompt:
Here's a task I do myself every week: [describe it]. Ask me the
questions you'd need answered to run it without me. Then tell me which
of my answers were actual rules and which were just preferences I've
never examined.Get the system this runs on — free
Don't start with a manual. Start by building one thing that does the work without you in it — so when somebody shows up, you have something to hand them instead of something to explain.
My inbox agent is the clearest example I've got of a system that can change hands. It triages my inbox three times a day whether I'm paying attention or not. I put the whole thing in a free kit — instructions, setup, all of it. Take it apart. If it doesn't work for your situation, tell me and we'll make it better.
Rather have it built with you? I do this with clients. Book a 1:1.
Baldomero Garza — Find me on X, LinkedIn, Instagram, or book a 1:1.
P.S. — If you do one thing this week: pick the task you'd hand over first, and instead of writing instructions for a person, build the thing that does it. Then see what's left to explain. That leftover is your real documentation. Watch on YouTube →