Etc. File #004 — If You Disappeared From Your Business for Two Weeks, What Would Stop?
Let's try something. Tomorrow morning, you disappear from your business.
Nothing dramatic. You're fine. But for the next two weeks, you're completely unavailable. No email, no texts, no "quick question." No logging in from vacation because you suddenly remembered something at 9:47 p.m.
What happens?
Can someone follow up with the prospect you talked to last Thursday?
Does anyone know which proposal template is the current one?
Can someone update the website without first figuring out who has the login?
Does the team know what needs to happen before that new client gets started?
Can someone pull the monthly numbers, and do they know where those numbers come from?
Who knows that one particular customer always needs something done a certain way?
And perhaps the most revealing question: how many times would someone text you anyway?
I know what it's like to be that person
Earlier in my career, I owned "all the things." I knew the processes and the history. I knew where things lived, who to call, which version to use, and what needed to happen next. If something fell into the space between departments or job descriptions, it had a pretty good chance of landing with me.
My boss at the time told me, "If you get hit by a bus, we're screwed."
It was meant as a compliment, and at the time, I took it as one and believed it was job security. Being the person everyone relies on can feel pretty good. You're trusted, you're valuable, and you know how everything works.
But here's what being that indispensable also looked like: I couldn't take a vacation without being interrupted – ever manage getting a contract signed while standing in a ride line at Disney World? I did. I also missed school events for my kids because I was the only one who knew how to finish a pitch deck.
There was always a question only I could answer, or something only I knew how to do, or some piece of history that lived in my head. I don’t say any of this looking for a pat on the back – I share it because it didn’t have to be that way.
Eventually I figured out that the problem wasn't that I knew too much. The problem was that too much of what I knew stayed with me. There's a big difference.
Your process isn't documented if the documentation is Alex
Every business has an Alex. Maybe it's the founder, or the office manager who has been there for 11 years. Alex knows how everything works.
Need to find an old contract? → Ask Alex.
Something weird happened in the CRM? → Alex knows the workaround.
Need to reorder something? → Alex knows the vendor.
A client has a question nobody understands? → Alex remembers what happened last time.
Alex is fantastic → Alex is also a system.
And that's a problem. Not because Alex is doing anything wrong; they’re probably doing a whole lot right. The problem is that the business has quietly built its processes around access to a person instead of access to information.
What if Alex gets sick? Or takes a vacation, or gets promoted … or leaves? Maybe Alex simply has 42 other things to do and doesn't need another "quick question." Suddenly the invisible system becomes very visible.
Step One: Find It
You don't have to disappear for two weeks to figure out where the dependencies are. Pick one area of your business (sales, billing, marketing, client onboarding, reporting, your CRM, vendor management, whatever) and ask four questions. I call it the Two-Week Test, and you can download a worksheet here or at the end of this post if you'd rather work through it on paper.
01 What would stop?
What literally couldn't happen if you, or another key person, weren't available? Maybe nobody else has access. Maybe nobody knows the process, or a decision can't be made without one person. Or maybe everyone knows what needs to happen, but only one person knows how to make it happen.
02 What would slow down?
These things wouldn't stop completely. Someone could probably figure them out … eventually. After searching email, the shared drive, the CRM, and three folders inexplicably named "Old." The information exists, and the process probably does too, but the path isn't clear.
03 What would generate a question?
The ones that start with "Where is...?", "How do I...?", "Which one do we use?", "Who handles...?", "What happens after...?" and "Do you remember why we...?" Every recurring "quick question" is a clue. It tells you that the information exists, but it isn't accessible where someone needs it.
04 What would keep going?
Pay attention to this one, too. What would continue without anyone noticing you were gone? Those are probably your real systems: the information is accessible, someone knows what happens next, the right people have access, and the process doesn't need one particular person to push it forward. This is what you want more of.
Step Two: Prioritize It
Finding the dependency is only the beginning, because not everything that breaks matters equally. If nobody posts on social media for two weeks, maybe very little happens. If nobody follows up with incoming sales leads for two weeks, that's a different story. If payroll can't run because only one person knows how to do it, that's different again.
So, once you know what stops or slows down, ask the more important question: if this stopped working for two weeks, what would it actually cost us? (Obviously, dollars matter, but don’t think only in dollars.)
Would you lose or delay revenue?
Could you lose a customer, or damage the customer experience?
Would employees be unable to do their jobs while work piles up somewhere else? Could you miss an important deadline, payment, or obligation?
Could it damage your reputation, or cost you an opportunity you don't get back?
Now look at that consequence alongside the dependency.
→ High dependency, low impact: probably annoying, but maybe not where you start.
→ High impact, low dependency: worth protecting, but you may already have a reasonable system.
→ High dependency, high impact: this is your priority.
Step Three: Fix It
This is where businesses tend to overcomplicate things. We need a new system, we need to document everything, we need new software, we need an AI agent.
Maybe. But before jumping to the solution, ask: what would a better way for this work to happen look like?
Maybe the knowledge just needs to be documented. Maybe someone else needs access, training, or authority, or ownership needs to be clearer. Maybe a seven-step process could become three steps, or a repetitive handoff should be automated. Maybe AI could retrieve the information, create the first draft, or answer routine questions. And maybe part of the process should stay exactly where it is, with the person whose judgment makes it work.
The answer may be one of those things. More likely, it's some combination of them.
The goal isn't to automate the process. The goal is to build a better way for the work to happen.
Start smaller than you think. Let's say your entire client onboarding process lives in Alex's head. You could map every workflow, buy a new platform, and launch a six-month transformation project. Maybe you should eventually, but the first move could be this: have Alex record a 10-minute walkthrough of what they do, turn it into a checklist, and give someone else the access they need to complete it.
Then look at the checklist. Which steps are repetitive? Which can be automated? Where could AI be useful? And which parts require Alex's judgment?
You haven't completely rebuilt client onboarding. But tomorrow, your business will depend less on Alex than it does today. That matters.
So after you identify a high-impact dependency, ask one more question: what's the smallest change we could make that would meaningfully reduce the risk? Start there.
How AI changes this conversation
When a business discovers that too much depends on one person, the conversation can move very quickly from "We need to document what Alex does" to "Can AI do what Alex does?"
Perhaps. But I think we're skipping a really important question: what are we making Alex do that doesn't require Alex?
If Alex spends hours copying information from one system to another, generating the same report, routing routine requests, hunting down information, or answering the same basic questions over and over, we shouldn't preserve that work simply because Alex has always done it. Automate it, let AI retrieve the information, build the workflow, and give Alex those hours back.
But first, understand what Alex actually does. A job that looks like 10 repeatable steps from the outside may contain dozens of tiny decisions Alex stopped consciously thinking about years ago. They know when the normal process doesn't apply. They notice when a customer request feels slightly off. They know why a step exists in the first place, and they remember what happened the last time the business made an exception. They know when to follow the process and when not to.
That's the difference between automating a task and replacing judgment.
Before you automate the process, understand the whole process. Before you give an agent the job, figure out what the whole job is. And before you decide Alex is replaceable, make sure you know everything Alex knows.
The goal isn't to make people replaceable
Good systems aren't about making your people interchangeable. They're about freeing people to do the work you need them for.
I want the person with 10 years of customer knowledge thinking about the customer, not spending their afternoon answering questions about where files live. I want the founder making decisions only the founder can make, not being the only person who knows what happens after someone fills out the contact form. I want the marketing person thinking about the message, not recreating the same process every month because nobody ever documented it.
AI and automation should make that more possible, not less. The best use of someone's time is their judgment, expertise, creativity, and relationships. Not remembering what the password is.
So, could you disappear for two weeks?
Maybe the answer is absolutely not. That's okay. The more useful question is: why not?
If the answer is because your clients value your expertise, your team needs your leadership, or there are decisions only you should make, that's one thing. However, if the answer is because nobody else knows how to send an invoice? That's definitely worth fixing. And if an AI agent can send the invoice? Great. Just make sure somebody understands what happens when the invoice is wrong.
Try it on your own business
The Two-Week Test worksheet walks through the same three steps on paper, one area of your business at a time.
Download the Two-Week Test worksheet
Etc. Takeaway: Find the dependency. Understand the consequence. Fix what matters first.
Don't assume the answer is documentation, automation, AI, or another person.
Understand the work before you choose the solution.