How to start delegating without losing your mind
Especially if you’ve been doing everything yourself for way too long.
Delegation sounds great in theory — until you try it.
You hand something over, hoping to buy back time, and after some time you get five follow-up questions, a task half-finished, or work that you end up redoing yourself.
That’s when the thought creeps in: “It’s easier if I just do it myself.”
It’s not that delegation doesn’t work. It’s that most small business owners are doing it backwards — expecting someone else to “take things off their plate” without giving them the tools to do it well. So how to learn to delegate productively?
The real reason delegation fails
It usually starts with good intentions. You’re overwhelmed, so you hire someone — maybe a VA, a site admin, or an assistant — to help.
You hand them something small, like logging receipts or sending follow-ups. But what feels simple to you is actually unclear to someone else. They don’t know your shorthand. They don’t see your mental to-do list. They don’t know how to “just do it the way you do.” So they ask questions. They check in. They miss things.
And suddenly you’re more stressed than you were before. That’s not their fault, or yours if that’s to day. It is the system that is missing and until someone shows you why, you cannot know that’s the case!
Start with what you already know
Start with something small and familiar, something you do regularly, almost without thinking, like updating a spreadsheet every Friday. Or chasing a materials delivery. Or sending out weekly invoices.
Pick one thing that always gets done (eventually), and walk through how it happens — out loud, in writing, or in a voice note.
What happens first? Where does the info go? What would “done” look like? That becomes your first process.
You don’t need fancy tools — just a way to share your structure
You can use ClickUp, Trello, a shared folder, or even WhatsApp. The tool doesn’t matter, what matters is that the person who is helping you can see:
What to do
When to do it
How to know they’ve done it right
and if they have an example to follow or a checklist to tick off, even better! The goal is not perfection — it’s consistency.
What letting go actually looks like
At first, you’ll want to check everything. That’s normal. You might feel unsure, or tempted to just jump in and fix it if it is not correct. Please refrain from doing so, try to explain to who is helping you why they need to correct something and how. Give them the tools to get it right next time.
When you catch yourself and choose to trust the process just enough to let it work the shift happens. One of my construction clients did this beautifully. They were behind on invoicing for months because the owner was the only one who “knew how it all worked.” We mapped out the basics, set up a template, and gave their VA a weekly rhythm to follow.
By week two, invoices were going out without any chasing. The owner stopped worrying about it. And they got paid on time, consistently, for the first time in ages.
Delegation isn’t about losing control
It’s about building systems that let you focus on what only you can do, while knowing that the rest is still getting done.
You don’t need to hand over your whole business. Just start with one piece. Give it structure. Let it run. And when it works? Do it again with something else!
Want to hand over the chaos (without creating more)?
That’s what the Systems Starter Kit is for.
We don’t just talk about what to delegate — we actually build the workflows and templates so you can do it without stress. Based on how you work, not some idealised version of operations.
If you’re ready to stop holding it all — but still want it done right — the Starter Kit is where we start.