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Is It Time to Get Out of Your Own Way? 7 Questions to Ask Before You Hire Support

  • Writer: Liz August
    Liz August
  • Nov 12
  • 2 min read

Let’s cut to it: if your business has turned into a daily game of “what fresh chaos is this?” — it might be time to get out of your own way and let someone else step in.

 

Because yes, you’re capable of doing it all. But should you?

 

The clients who come to us aren’t new to business. They’re smart, savvy, and scrappy. But somewhere between scaling their services and onboarding their fifth client while muttering "I got it," something breaks. (Usually their sanity.)

 

So if you’re wondering whether now is the right time to hire help, start here:

 

7 Questions to Ask Yourself Before Hiring a Virtual Assistant or Integrator:

  1. Are you doing too much in your business?

  2. You wear all the hats. And the shoes. And the coat. No wonder it feels heavy.

  3. Are you still responsible for most of the moving pieces?

  4. Client work, emails, content, tech, scheduling... If it stops without you, it’s a you-sized bottleneck.

  5. Do you feel spread way too thin?

  6. There’s a difference between being busy and being buried. Which one are you?

  7. Are you actually ready to give up control and trust an integrator?

  8. Hiring support means letting go. If you’re not ready to delegate, nothing will change.

  9. Can you think like a true CEO?

  10. The visionary's lane is high-level, long-term, big-picture stuff — not troubleshooting broken forms or setting up CRMs.

  11. Do you have workflows and processes for day-to-day operations?

  12. If you’re relying on memory, DMs, or your inbox as a task manager… we need to talk.

  13. Can you financially afford it?

  14. This doesn’t mean “do you have cash lying around?” It means: are you spending so much time doing that you’re not earning what you could?

 

What to do if you’re saying “Yes” to most of these…

 Start with a Strategy Session.

 

It’s not fluff. It’s not an upsell. It’s the first step in figuring out what kind of support will actually move the needle — whether that’s systems, tech, admin, or a little of everything.

 

You talk. We listen. Then we build a custom plan that gets you out of the weeds and back to thinking like a CEO.

 

👉 Book your Strategy Session here — and let’s make burnout a thing of the past.

What Our Clients Say

Liz and the Simplify, Simplify team are miracles in my life. If you are struggling with technology in your business, Liz starts there, but before you know it, she’ll be handling so much of your life you’ll wonder how you ever survived without her.

- Judi Harrington, Copywriter & Writing Coach

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Made with 💙 + 🥤 in Worcester - the ancestral lands of the Nipmuc

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