Building a team is one of the most exciting milestones of scaling a business, but growth is rarely a straight line. One of the most difficult shifts for any entrepreneur is realizing that a partnership that once worked—or one you desperately wanted to work—is no longer serving the business.
Whether the mismatch is in skill set or communication, knowing when to pivot is essential for your sanity and your bottom line. Here are the four key signals that it’s time to part ways with your virtual assistant (VA) and find a more sustainable path forward.
1. The “Broken Record” Syndrome
Communication is the bedrock of delegation. However, if you find yourself clarifying the same expectations and resetting the same boundaries month after month, you have a problem.
If the same issues continue to arise after you have provided clear feedback and reset communication channels, it’s usually not a “misunderstanding” anymore—it’s a lack of alignment. Your time is too valuable to spend it repeating instructions that aren’t sticking.
2. The Skills Mismatch (The Growth Gap)
As your business evolves, your roles will too. Sometimes, a VA who was perfect for your “startup phase” simply doesn’t have the technical depth or skill set required for your “scaling phase.”
It’s important to remember: This is a mismatch, not a failure. Just because they aren’t the right fit for your new requirements doesn’t mean you hired incorrectly back then; it just means your business has outgrown its current support structure.
3. The “Stomach Flip” Test
Pay attention to how you feel when you see a notification from your VA or realize you need to have a check-in. Are you excited to collaborate, or are you feeling a sense of dread?
If you are constantly feeling stressed about having to address ongoing issues or “fixing” their work, the relationship is no longer providing support—it’s creating a new task on your to-do list. Sustainable support should bring peace of mind, not a higher heart rate.
4. Moving from “Hiring Correct” to “Learning What You Need”
Many founders stay in stagnant relationships because they feel they “failed” at hiring. Ending a VA relationship doesn’t mean you failed at hiring; it just means you finally learned what you actually need.
The goal of your business is not to make a specific relationship work at all costs. The goal is to build a team that allows you to step back from the “Operator” seat and move into the “Owner” vision.
The Bottom Line
Parting ways with a team member is never easy, but holding on to a mismatch prevents both you and the VA from finding a better fit. When you let go of what isn’t working, you create the space to find the top 1% talent that will actually move the needle.
Not sure if you need a new VA or a different support model entirely? Take our Delegation Quiz to identify the exact support your business needs to reach the next level.
Need urgent support? Book a consultation today.