If you've ever hired someone to help relieve the overwhelm you feel in your business and you still feel like you're doing everything yourself, this episode is for you. Because I'm going to be talking about why you keep failing at delegation—and spoiler alert, it's probably not the reason you think.

It's not about who you hired. It's about what you hired them into.

Whether you're the CEO trying to grow your business or you're just trying to get control of your time and get time back, your systems matter. Delegation isn't the problem—but your back end might be.

So let's talk about it.

Welcome to the Mind Your Time podcast. I'm Shannon Baker, your coffee-loving host and business operations strategist. If your business feels chaotic and you're tired of spinning your wheels, you're in the right place. Each episode contains bold strategies and practical insights rooted in my POWER In Motion Framework to help you streamline your operations, reclaim your time, and grow without burnout.

Whether you're just starting out or scaling to six figures and beyond, I’ll help you simplify, set boundaries, and build a business that works for you. So grab a cup of coffee or your favorite beverage and let's dive in.

Okay, so let me start by taking you back to one of the first clients that I ever worked with as a virtual assistant. We're going to call her Melissa.

On the outside, everything in her business looked amazing. She was almost making six figures, she was booking speaking gigs, and she had a waitlist full of dream clients. But once I got to look behind the curtains and see the real deal, her business was a mess.

There were no SOPs. No task management system. Nothing was documented. It was just pure chaos.

During her discovery call, I noticed some red flags that I should not have ignored. She was very vague about how she worked and couldn’t explain her processes. Honestly, she was pretty scattered. But I ignored all those red flags because I was new—and I truly believed I could help her.

Well, guess what? I couldn’t.

Every time I tried to create structure in Melissa's business, she got flustered. Sometimes she even ghosted me. One day she said I was giving her too much work—when all I had done was try to introduce some clarity and organization.

Needless to say, I ended up firing her as a client.

That was the moment I realized: delegation isn't always the issue. Nine times out of ten, the real problem is the backend of the business.

I remember sitting at my desk wondering, “Is it me? Am I asking too much?” But deep down, I knew I wasn’t. I was asking for basic things: clarity, communication, and structure.

That’s when it hit me—it wasn’t about my effort. It was about her readiness.

And that moment has stuck with me ever since. Because I’ve seen it happen time and time again—especially with women who are purpose-driven and laser-focused on reaching their goals.

So let’s talk about this for real.

If you're anything like my client Carla—this is a different client—then you’re probably thinking delegation just doesn’t work for you either.

You’ve handed off a few tasks here and there. Maybe you’ve hired a VA once, twice, even three times—and each time it’s failed. Somehow it always ends up the same.

Tasks fall through the cracks. You repeat yourself constantly. And eventually, you just do it yourself.

So you tell yourself, “It’s easier if I just handle it.”

But here’s the truth: you aren’t failing at delegation. You’re trying to delegate into disorganized—or nonexistent—systems.

Let’s say you hire someone and say, “Just help me. Jump in wherever I need support.” Sounds reasonable, right?

But without clear expectations, documented steps, or a system for them to plug into, they’re left guessing. And guesswork leads to mistakes. Mistakes lead to mistrust. And suddenly you’re back in the weeds, stressed out and burned out, doing it all yourself again.

The problem isn’t that you hired the wrong person. It’s that your backend wasn’t ready to support them so they could support you.

Now hear me out. I’m not saying you need to build a 200-page SOP manual overnight. But you do need a system—a foundation that gives your support team clarity, direction, and documentation so they can actually help.

That’s where the Back Office POWER Checklist comes in.

It’s the very first thing I give to anyone who’s preparing to hire or who’s had a poor experience with delegation. It helps you take an honest look at what’s working, what’s missing, and what’s creating bottlenecks behind the scenes.

Because if your business is built on adrenaline and last-minute decisions, no VA in the world can keep up. But if you give them a roadmap, show them the big picture, and provide a little breathing room—they can help you lead.

That’s exactly what one of my clients—let’s call her Carla 2.0—did.

She came to me totally over it. She’d already sworn off hiring another VA because it had “never worked.” She said it was more stress than support.

But during her POWER In Motion Jumpstart Session, we did something different.

Instead of rushing to fill in the gaps, we slowed down. We walked through the Back Office POWER Checklist together. And that one step changed everything.

She saw exactly where her systems were fuzzy, where handoff points were failing, and where her expectations were still stuck in her head. That clarity shifted everything.

By the end of her session, she didn’t just feel ready to hire—she felt equipped to do it differently. She had a starting point, a 30-day focus, and a way to prepare for the kind of support she actually wanted and needed.

For the first time, she wasn’t hiring from the verge of burnout. She was hiring with intention.

Her plan now is to bring on a VA who can truly grow with her. And when she does, she already knows what that onboarding process will look like—because we mapped it out together.

She’s planning to enroll them into Founders Circle after 90 days of working together, and they’ll use the Delegate with Confidence Guide to co-build the backend—without Carla becoming the bottleneck again.

What a difference preparation makes. And it started with one honest look at what was happening behind the scenes.

That’s what I want for you, too.

So let me ask you—do you really know what kind of support you need? Or are you hoping someone will just figure it out for you?

Do you have a repeatable way to hand things off? Or are you winging it every time something comes up?

Answer those questions honestly.

Here’s your quick win challenge this week: Download the Back Office POWER Checklist and complete it—truthfully. Don’t sugarcoat. Don’t skip the messy parts. If it’s slowing you down or making delegation harder, it needs to be addressed.

This isn’t just the first step to hiring. It’s the foundation for building a business that supports the growth you want.

Now let’s wrap this up with three mindset shifts that can change your entire approach to delegation:

First, hiring isn’t the fix—preparation is. If your backend is chaotic, it won’t matter who you hire. You have to make space for them to succeed.

Second, delegation works when you lead it well. That doesn’t mean micromanaging—it means providing structure, context, and a system that helps your team step into their role with confidence.

Third, you don’t need a massive overhaul to see results. Sometimes one focused audit or a 30-day plan is all it takes—just like Carla 2.0 experienced.

If you’re ready for support that actually sticks, download the Back Office POWER Checklist now. And if you want personalized guidance as you walk through it, book a POWER In Motion Jumpstart Session. In one hour, we’ll create a 30-day action plan that gets your backend ready for the kind of support that can help you thrive.

You don’t need to do more to make your business run better. You just need the right foundation.

Let’s build it together.