Hiring an Admin: Where to Start
(and why you don’t have to do this alone)
Most founders don’t start out wanting to do everything themselves. It just… happens.
At some point, you realize you’re the one creating marketing materials, managing calendars, researching software, fixing billing issues, and yes—occasionally schlepping snacks for a staff meeting. Not because it’s the best use of your time, but because there’s no one else to do it.
You’re tired. A little resentful. More stretched than you want to admit.
Meanwhile, there are staff issues bubbling up, projects going sideways, customers getting frustrated, and accounts payable inching toward panic.
“I don’t see how this can possibly change,” a client once told me.
I understood exactly what he meant.
The saddest, loneliest-looking office I could find in stock images. Don’t be this guy!
Why This Feels So Hard
If you built your company from nothing, stepping back can feel impossible. You’ve been the glue, the safety net, the decision-maker. Money feels tight. Time feels nonexistent. Every day is some version of putting out fires.
So the idea of making change—especially hiring help—can feel overwhelming. Like one more thing you don’t have room for.
Here’s the part I want you to hear clearly: you were never meant to do this alone.
Why Coaching Is the First Step
Your business didn’t land here by accident. It got here through a thousand small decisions—some intentional, some made under pressure, some made simply to survive another week.
Coaching creates a pause in the momentum. A place to step back and look honestly at:
How you’re spending your time and energy
What you’re holding onto that no longer serves you
What truly requires your leadership—and what doesn’t
This isn’t about judgment or fixing you. It’s about clarity. And self-trust. And building the capacity to lead differently.
Without that foundation, hiring an admin can feel frustrating or disappointing. Not because they aren’t capable—but because delegation is a skill most of us were never taught.
Where an Admin Actually Helps
This is where an Admin—Virtual Assistant (VA) or Executive Assistant (EA)—can be incredibly powerful.
Many founders believe they need to get organized first. That once the systems are perfect, then they’ll bring someone in. In practice, the opposite is almost always true.
The most effective leaders I know make change with support, not in isolation.
The order matters:
Coach → Admin → Systems
Virtual Assistant vs Executive Assistant: What to Hire First
Virtual Assistants (VA)
For many leaders, a VA is the gentlest—and smartest—place to start.
A VA can take real weight off your plate right away:
Email and inbox management
Scheduling and calendar coordination
Payroll and bookkeeping support
Day-to-day administrative tasks
But the deeper value comes over time. A good VA notices patterns. They see where the same task keeps popping up, slightly differently each time. They help document how things actually work, not how you wish they did.
Think about your sales process. Is every new client welcomed the same way? Is their information easy to find later? Are there steps that quietly fall through the cracks, only to reappear as stress?
Start small. Capture the obvious workflows first. The systems will grow naturally from there.
In-Person Admin, Office Manager, or Executive Assistant
An in-person Admin can be transformative—but timing matters.
I rarely recommend hiring in-person support as a first step. Working with a VA for 6–12 months builds the muscle of delegation. It helps you see how much you’ve been carrying, and what kind of support actually helps.
With that clarity, an in-person EA or Office Manager isn’t just helpful—they’re empowered to succeed.
A More Sustainable Way to Lead
Hiring an admin isn’t just an operational decision. It’s a leadership one.
When paired with coaching, administrative support doesn’t just reduce your workload—it changes how your days feel. Less frantic. More intentional. More aligned with why you started this business in the first place.
If you’re considering hiring a VA or EA and aren’t sure where to begin, I’m happy to talk through what I’ve seen work—and what doesn’t.
You don’t have to carry all of this alone anymore.
Ask me about my experience with fractional and virtual assistant services! Schedule a one-hour consultation to begin unpacking what you and your business need. Let’s build a business you want to live with.