- Mollie Staretorp
- Feb 27
- 3 min read
Updated: Sep 9
At some point in the founder journey, the support that used to feel helpful starts to feel like another thing to manage.
You’re assigning tasks, but they come back half-done. You’re still handling decisions. You’re spending more time reviewing than you would doing it yourself.
If this sounds familiar, it’s not a failure — it’s a milestone. Most early-stage founders start with generalist VAs to handle basic admin. But as the business grows, so do the expectations, tools, and complexity. The support model needs to grow with it.
Here’s how to know when you’ve outgrown your current VA — and what to do about it.
5 Signs You’ve Outgrown Your VA
1. You’re still the default for everything.
Even with a VA in place, all decisions still come through you. Nothing moves unless you push it — and it’s exhausting.
2. They require constant instructions.
Every task needs step-by-step guidance. There’s no initiative, no foresight, and no system-building.
3. Delegation is costing you time, not saving it.
By the time you explain the task, review the result, and clean it up, it would’ve been faster to do it yourself.
4. Tool usage is limited or outdated.
Your VA struggles with the tools your business now relies on — or avoids them entirely. You’re stuck bridging the gap.
5. You’re managing the assistant, not being supported.
Instead of expanding your capacity, your VA has become another person to manage — which defeats the purpose entirely.
Why This Happens
Most entry-level VAs are trained to complete tasks — not to think like operators. They do what they’re told, but they’re not equipped to:
Anticipate what’s next
Understand context
Improve workflows
Communicate with stakeholders
Operate across tools and systems
This model works when your business is simple. But when you’re juggling investor meetings, team ops, product launches, and growth goals — it breaks.
What you need is no longer a basic assistant. It’s an Executive Virtual Assistant (EVA).
What an EVA Can Do Differently
An EVA is trained to support executive workflows and business operations at a higher level.
That includes:
Managing calendars, meetings, and comms across stakeholders
Building and maintaining SOPs
Drafting emails and documents with context
Running workflows and light project management
Using AI tools and automations to remove manual work
Acting as an internal point of coordination
You stop being the only person with context. Your EVA becomes a second brain for your business.
What to Do Next
If you’re ready for a higher level of support:
Acknowledge the gap.
Your current VA may be doing their best — but their role isn’t set up to meet your current needs. That’s not failure. It’s growth.
Document what’s changed.
List the tasks, tools, or decisions that feel bottlenecked. These are the handoffs that your next assistant should be able to own.
Decide whether to upskill or upgrade.
Some VAs can grow with you — others can’t. If you find yourself training your assistant on tools and executive thinking, it may be time to bring in someone who’s already operating at that level.
Redesign the role.
Whether you continue with your current VA, promote them internally, or replace them with an EVA, redefine the role around ownership and outcome — not just task support.
You’re Not Being “Too Demanding.” You’re Evolving.
Founders often stay too long with the wrong support because they feel bad about moving on. But needing more is a sign of progress — not impatience.
You’ve grown. Your systems have grown. The assistant model that got you through the early stage won’t get you through the next one.
This isn’t about replacing help. It’s about replacing friction — and getting the kind of strategic support that actually keeps up with you.
Further Reading
The Difference Between a VA and an EVA — and Why It Matters
How to Turn Your VA Into a Strategic Partner
Why Delegation Fails (And How to Fix It)
Managing a VA: Tools, Routines, and Boundaries That Work
