You know the fastest way to make a “simple” task take an entire afternoon?
Hand it to someone else and then spend the next two hours answering questions about how to do it and pointing out the “tiny” mistakes that become massive frustrations.
Like when GIFs are your love language, and you include them in all forms of communication only to check on a post and discover… The GIFs aren’t GIFing.
Because when you start delegating, it’s not the work that gets you. It’s the handoffs. The tiny details. The micro-decisions. The “wait, where did you put that?” and “which version is the right one?” and “why did you set the heading size to be 16 when it should be 18?” spiral.
Whether you delegate to humans or AI, if you’re reading this like, “Alison… I feel attacked,” trust me, I’m calling myself out too!
When we make things “complicated”
When I first started this newsletter, it was honestly pretty straightforward. I had AI help me pull out my story, my takeaways, and a weekly challenge, and then I’d drop it into an email and hit send.
Done. Easy. Very main-character energy.
Then I decided to repurpose the content for broader distribution (because, of course, I did).
So I added the blog. Then a LinkedIn newsletter. Then eventually a podcast and, most recently, a paid version that goes deeper.
And every time I added one more place this content needed to go, a bunch of “small” things quietly showed up with it. Little tweaks to the copy, different formatting, different CTA language so it actually made sense on each particular platform.
Same content. Different rules. Nothing hard. Just a lot.
When I first started over a year ago, I hadn’t documented any of the process. Not because I was being careless; it just never occurred to me. I was doing it myself, so I didn’t need instructions.
I knew what “right” looked like.
Then my business grew, my calendar got tighter, and my brain got louder, especially as my newsletter started to gain traction in all the different places.
Finally, I made the responsible CEO decision: “I’m handing off distribution.”
Except that handing off distribution when nothing is documented is how managing the task becomes more time-consuming than doing the task.
Now understand that my VA was completely capable. It was more like I gave general instructions (grab the copy from my Google Drive and go post in these 3 places) and then I’d go check on it and realize a bunch of tiny details were, well, wrong.
Headings weren’t the size I wanted. CTA’s didn’t match the platform. And yes, on occasion, a file wasn’t uploaded properly, which meant that my GIFs weren’t GIFing!
So now I was doing the work and being the Quality Control Department and being the Process Translator and being the final boss of “tiny details that somehow matter.”
Which is how “delegation” turns into the thing that makes you want to take the task back, and because it’s either that or you’ll LOSE.YOUR.MIND.
The Handoff Tax
If you can relate this at all, as much as we both might not want to admit it, this generally isn’t a “team member problem.” It’s a workflow problem.
Because when the workflow isn’t mapped, every handoff costs you. Every owner change creates friction. Every unclear step turns into a question. And every mistake turns into time wasted.
You end up being the bottleneck, whether you mean to or not, and it’s the reason “simple” work is stealing your week.
Personally, that stings because I was literally setting up systems and workflows for other people’s business for a living!
The good news is that I also knew you don’t fix this problem by working harder, micromanaging more, or magically finding the world’s most perfect team member.
You fix it by defining the path so the work can move without you pushing it forward every time.
I say that to say this, because yes, in my case, I did end up making a team change. Not because my old VA was a bad person, but because the role needed a different personality type.
The point I want to drive home, though, is that “fix” wasn’t the new person. The fix was the structure.
Fast forward: months later, I finally built a fully mapped-out system for this newsletter distribution. Like, fully.
I still owned the content creation (that’s my lane), and I still used AI the way I always have to help me draft it.
But everything after that? The distribution, the formatting standards, the platform-specific tweaks, the CTAs, the exact “this goes here, then here, then here” steps… it all got documented (right down to the details that used to make me twitch).
My new VA walked into a documented path, and that’s what made consistent execution possible because she knows exactly what needs to be done and when I see something I want changed, we document it!
And I’m seeing the same pattern across my business with my webinars, podcast workflows, content repurposing, and lead gen.
ALL of it got easier when the “tiny details” were written down where someone can actually follow them.
My VA isn’t waiting on me. She’s proactive.
She gets things done before I “assign” them because she already knows what’s next. She’s not blocked by questions. She’s not guessing. She’s not doing trial-and-error every week.
She’s moving me forward… not the other way around, because I am no longer fixing mistakes, which means I can focus on revenue-generating activities that have scaled my business.
Weekly Challenge
Remember last week’s backend triage, where you circled the one backend fire that makes everything harder?
This week, don’t “fix” it. Just make it transferable.
- Pick that one workflow.
- Record a quick Loom of you doing it start-to-finish (messy is fine).
- Create a rough SOP from it (bullet points are perfect). Make sure it answers:
- What are the steps, in order?
- What does “done” mean?
- Where does it live (tool/link/location)?
- Where are the handoffs (who owns what, and what triggers the next step)?
That’s it. The goal is to stop losing time to rework and “tiny detail” corrections.
*And if you want the exact AI prompt I use to turn that Loom/transcript into a clean SOP, that’s going in The Caffeinated Entrepreneur: The Refill that drops tomorrow!
What’s your version of “the GIFs aren’t GIFing?”
Reply to this or DM me and tell me the tiny detail that makes you absolutely feral when it’s wrong. The thing that seems “small” to everyone else, but you’re over here double-checking it like it’s a life-or-death situation.
(Fonts? Links? Spacing? Subject lines? Calendar invites? The way a PDF is named? I want the stories.)
Thanks for reading. Keep showing up, keep taking the next step, because the caffeine is strong… and so are you.
Till next time!
The Caffeinated Entrepreneur: The Refill is for the people who are done “getting inspired” and are ready to actually fix the thing.
Every week, you’ll get the deeper breakdown + copy‑paste AI prompts/templates that turn the free newsletter’s challenge into implementation… because screenshots don’t count as execution.
If you want the extra shot (and you’re not looking for an easy button), subscribe to The Refill.
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The Caffeinated Entrepreneur: the Refill
For the people who are done “getting inspired” and are ready to actually fix the thing. Every week, you’ll get the... Read more |
