April 1, 2025
You’re not going to be able to grow and scale your business without growing and scaling your team. And that means learning to delegate. In this episode of Bringing Simplicity Unfiltered, Greta and Judy get honest about why delegation is so hard for high achievers and perfectionists, including themselves, and what actually makes it work.
Greta has helped scale two companies to $1 million. Judy has worked with multiple CEOs scaling to seven and eight figures, including one company that went from $7.5 million to $14 million in three years and hit the Inc. 5000 list twice. Even so, they admit they aren’t always as good at doing this for themselves as they are for their clients. Here’s what they’ve learned.
Judy likes to frame it from a pain point: how devastating would it be for your clients, and your clients’ clients, to lose support because you never delegated? If you don’t delegate, you’re going to burn out, your team is going to burn out, and if something ever happened where you couldn’t work, everything would stop.
When you delegate, three things happen:
The first step is admitting to yourself that delegation is an area of opportunity for you, then deciding and taking action.
You can exercise this muscle before you ever delegate a single task. Greta used to think, “This is something I’ll always own, so I don’t need to document it as thoroughly.” The reality is you should be documenting everything.
Judy has pushed Greta to keep Loom running. Once, when Greta was out of office, Judy took a Loom Greta had recorded, followed the mouse movements, and completed the task correctly. Any documentation, even if it’s not perfect, is better than no documentation. It gives the next person somewhere to start.
That’s a line from a book Judy and Greta were both reading at the same time (Greta admits she wrote “eek” next to it because she knew that wasn’t her yet). Gary Vee says something similar: document, don’t create. When you document and share it, it’s there for other people.
Team members often hang on to information without meaning to, because they want to be needed. If there’s no SOP, people can always count on them. But when they see you, the CEO, documenting everything without fear, it models the abundance mindset that there’s always room to grow. Your team doesn’t do what you say. They do what they see you do.
Greta’s mistake as an overachiever was assuming she could say “I want a landing page for this opt-in” and someone would knock it out of the park. That’s unrealistic. They don’t have her years of experience or her brain.
Dan Martell’s 10-80-10 rule fixed that:
That last 10% gets faster and faster the more projects you do together.
Judy’s take: the greatest way to be disappointed is to have expectations. You can (and will) have high expectations as a business owner, but when you start delegating, remember you’re not going to be the best delegator yet. As Greta put it, it’s probably you, not the people you hired.
One of the most common things missing in delegation is a timeframe. Give the task, the SOPs, and your expectations, then ask them to confirm they’ve read the SOPs by a certain date.
Set the due date before you actually need it. We usually build in a three to four day buffer. If you really need it done Thursday, ask for it by end of day Tuesday so you have time to review and test it before it goes live.
Telling someone “that wasn’t what I wanted” can be uncomfortable, especially with VAs. But how would anyone ever get better without real feedback? Be kind and gracious about it. A lot of people are quick to fire someone, when the real problem was that they weren’t clear on their own expectations. Often feedback becomes an open dialogue about how to improve the process itself.
Judy recommends the book Crucial Conversations for leaders who want help with these conversations. Come from the frame that nobody wants to do a bad job. Point out what went well, share pointers for next time, and keep going. If someone keeps underperforming after multiple rounds of feedback, it won’t be because you didn’t help them improve. In our experience, people who aren’t ready to be around high performers will often quit on their own.
We check in with team members to ask how things are going, whether they’re enjoying the work, and what they’d change. One excellent team member recently suggested two or three things that would streamline her job, and we said, “Awesome, look into it, let’s do that.” In order for delegation to be fun, you have to be willing to hear feedback, good and bad. Your success is only as good as your team’s success.
Layla Hormozi reportedly blocks her Fridays for team syncs. Schedule your own. Have these conversations over video or voice whenever you can, not text or email, because written messages remove the human touch. If you’re short on time, record a quick Loom.
And be transparent. Your team often thinks you know everything. Let them know you’re expecting them to master this skill, because their skill set is how the company is going to grow.
Document the task first (a Loom recording is fine), start with something small that takes under 20 minutes to check, hand it off with clear expectations and a deadline, ask for feedback on your instructions, and review their work with a quick Loom.
From Dan Martell, it means you spend the first 10% setting clear expectations, the team member does 80% of the work, and you spend the final 10% reviewing, cleaning it up, and giving feedback.
We usually build in a three to four day buffer, so if you need something Thursday, ask for it by end of day Tuesday. Expect the first attempt to take at least three times longer than it takes you.
Video or voice whenever possible. Text and email remove the human touch. If you’re short on time, record a short Loom.
If you’ve done it twice, document it. Even imperfect documentation is better than none.
If you’re growing your team and want help building systems that scale, learn more about Bringing Simplicity or reach out to us.
Want more? Watch every episode of Bringing Simplicity Unfiltered on our YouTube channel.
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