Hiring a VA or OBM Won’t Save You If You Don’t Have This First
By Eloisa Guynn
Let’s have the honest conversation most people avoid. Hiring a virtual assistant (VA) or an online business manager (OBM) will not save your business from disorganization, burnout, or operational overwhelm—especially if the business systems you’re plugging them into are a mess.
We see it all the time. Founders who are stretched thin and overwhelmed look to hiring as the answer. They bring on a VA or OBM hoping this person will take everything off their plate, bring order to the chaos, and magically know what to do. But weeks in, they are still frustrated. Tasks are slipping, things are being done differently than expected, and instead of feeling relieved, they feel like they’re managing even more.
The truth? Hiring someone into dysfunction will only scale the dysfunction.
This is not a knock on VAs or OBMs. There are some incredibly talented professionals out there—people who are proactive, strategic, and deeply committed to helping your business thrive. But just like in any industry, there are also folks who overpromise and underdeliver. And none of that changes the reality that as the founder, you are responsible for what they’re walking into. You set the tone. You define the systems. You provide the structure—or lack thereof.
If your VA or OBM is scaling chaos, that’s not on them. That’s on you.
So before you hire help, let’s talk about what you actually need to have in place to ensure that support is effective, empowering, and scalable.
The VA or OBM Is Not the Fix
Let’s start with the obvious. A VA or OBM is not a Band-Aid for broken business operations. If you are disorganized, unclear on your goals, reactive in your decision-making, or constantly reinventing how things get done, then bringing in support is not going to solve your problems. In fact, it may make things worse.
Because what happens when you delegate into dysfunction? You get confused deliverables, wasted time, missed deadlines, and mutual frustration. You end up micromanaging or redoing work entirely, which is the exact opposite of what you hoped hiring would give you.
The fix is not the hire. The fix is the system they are stepping into.
What Most Founders Get Wrong
The biggest misunderstanding I see is the belief that once you hire the right person, they will just “take it and run.” That they will automatically know what to do, how to do it, and how to make decisions the way you would. But unless you are hiring a high-level operator into a fully documented and structured business (which, let’s be real, most aren’t), you are setting them—and yourself—up for failure.
Here is what most founders skip:
Sharing their business’s vision and values in a meaningful, practical way
Outlining how they make decisions and what their priorities are
Clarifying what success actually looks like for the role being hired
Providing documentation for how things are done
Your team cannot operate like you do unless you give them access to how you think, what matters to you, and what your expectations are
Structure Always Comes Before Support
Before you bring someone into your business to “own” an area, you need to define what ownership means in your world. Structure is not optional. It is the prerequisite to support.
Think about it this way: if your business were a building, you would not bring in a decorator before laying the foundation. Yet that’s what so many founders do. They look for someone to “make things better” before the basics are in place.
Here is what structure looks like:
Clear, documented processes (SOPs) that explain how tasks should be completed
A shared understanding of your mission, vision, and values
A communication rhythm and decision-making framework
Defined KPIs or outcomes for each role
Expectations around timelines, ownership, and accountability
If you cannot hand off a process and reasonably expect it to be completed accurately without your constant involvement, you are not ready to delegate. You are trying to outsource leadership without providing leadership.
Yes, Great VAs and OBMs Exist—But You Still Have to Lead
Let me say it again for the people in the back: this is not about discrediting amazing VAs or OBMs. There are some truly excellent professionals out there who will go above and beyond to support your vision, create systems, and document processes with you.
But they cannot do it alone. Not in the beginning.
You have to provide guidance. You have to explain. You have to share how you think, what you value, and how decisions get made. You are not just hiring help—you are onboarding someone into a business you have built, with all the nuance, context, and complexity that comes with it.
Even the most experienced OBM cannot compensate for what you have not made clear.
And if you do find someone who helps you document and clarify things? Wonderful. That’s a powerful investment. But it still requires time and collaboration. It is not an overnight fix, and it is not passive. You will need to lead them through it.
Not Everything You Do Is Scalable—and That’s a Problem
Here is something no one tells founders enough: if your processes are too complicated to explain, they are not scalable. If you are constantly making exceptions, improvising solutions, or relying on your memory to get things done, then you are not delegating—you are duct taping.
Scalable businesses are built on clarity. They are built on repeatable processes that can be handed off and executed consistently. They are built on systems that empower your team to make decisions without relying on your every input.
Ask yourself:
Could someone else repeat this process without asking me 10 follow-up questions?
Do I have documentation that shows exactly how something should be done?
Are my expectations clear, realistic, and measurable?
If the answer is no, that is your next step—not another hire.
The Real Work Is Upfront—but the Payoff Is Long-Term
If you are hiring because you are overwhelmed, it might feel discouraging to hear that you need to do more work upfront. But this is not extra work. This is the work. And once it is done, everything else gets easier.
When you build clarity into your business—clarity around how things are done, why they are done that way, and what success looks like—you unlock the full potential of your team. You can finally delegate without doubt. You can trust the process. You can scale without being in every detail.
That is what most founders actually want when they hire. They want freedom. But freedom is a result of structure, not just support.
Accountability Is Empowerment
Let’s be real. If you have hired support and it has not gone the way you hoped, that is not a sign that you failed. It is a sign that there is a gap in your foundation that needs attention.
So instead of beating yourself up, take accountability. Learn from it. Set aside the time to create the clarity your team needs to do their best work.
This is not about blame. It is about ownership. You are the founder. That means you are responsible for creating the environment your team steps into. And when you build it well, great people can thrive in it.
Final Thoughts: Clarity Before Delegation
If you are hiring because you are overwhelmed, burned out, or buried in the weeds—and yet nothing seems to get better—it is time to look at what you are handing off.
Questions to ask yourself:
Are your expectations clear?
Do your systems support your vision?
Have you built a business your team can actually succeed inside?
If not, then you do not need another hire. You need clarity. And we can help you build it.
Ready to Build a Business That Supports the Support You’re Hiring?
Book a Business Clarity Session and let’s identify the gaps, build the structure, and create a business that can actually grow with you—not just depend on you.
Clarity comes first. Delegation gets easier after that.
TL;DR
Hiring a VA or OBM without structure is not delegation, it's outsourcing confusion
Clear expectations, SOPs, and operational frameworks must come first
Great hires still need leadership, onboarding, and ongoing support
VAs and OBMs are not the problem, but they cannot solve broken foundations
As the founder, it’s your responsibility to create clarity before bringing others in
Document your processes, define how you think, and give your team the tools to succeed
Delegation works when your business is ready to support it
