238. Why Your Assistant Isn’t Working (And How to Fix It)
Tue Sep 02 2025
Everyone loves to tell busy founders, “You need an assistant!” But here’s the problem not all assistants are created equal. And if you hire the wrong one, you’ll waste money, get frustrated as hell, and end up thinking assistants don’t work.
In this episode of World’s Greatest Boss, I break down the three main types of assistants: Virtual Assistant (VA), Personal Assistant (PA), and Executive Assistant (EA).
You’ll learn exactly what each one does, the benefits and drawbacks, signals that it’s time to hire, and how to actually find the right one. By the end, you’ll know which assistant can buy back your time without making a costly hiring mistake.
What You’ll Learn in This Episode:
The core differences between a VA, PA, and EAThe biggest mistake founders make when hiring an assistantSigns that you’re ready for each type of assistantThe real costs (and hidden costs) of these rolesWhere to find the right assistant for your needs
Why This Matters:
Hiring the wrong kind of assistant is one of the most expensive mistakes you can make as a founder. Whether you’re drowning in repetitive admin tasks, losing weekends to errands, or stuck in the weeds of business operations, the right assistant can give you back your time — and your sanity.
Resources and Links:
Connect with Jackie on LinkedInLearn more at People PrinciplesDan Martell’s book: Buy Back Your Time
If you enjoyed today’s episode:
Subscribe to World’s Greatest Boss wherever you listen to podcastsLeave a review to help more business owners find the showShare this episode with a founder friend who’s overwhelmed and needs help
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Everyone loves to tell busy founders, “You need an assistant!” But here’s the problem not all assistants are created equal. And if you hire the wrong one, you’ll waste money, get frustrated as hell, and end up thinking assistants don’t work. In this episode of World’s Greatest Boss, I break down the three main types of assistants: Virtual Assistant (VA), Personal Assistant (PA), and Executive Assistant (EA). You’ll learn exactly what each one does, the benefits and drawbacks, signals that it’s time to hire, and how to actually find the right one. By the end, you’ll know which assistant can buy back your time without making a costly hiring mistake. What You’ll Learn in This Episode: The core differences between a VA, PA, and EAThe biggest mistake founders make when hiring an assistantSigns that you’re ready for each type of assistantThe real costs (and hidden costs) of these rolesWhere to find the right assistant for your needs Why This Matters: Hiring the wrong kind of assistant is one of the most expensive mistakes you can make as a founder. Whether you’re drowning in repetitive admin tasks, losing weekends to errands, or stuck in the weeds of business operations, the right assistant can give you back your time — and your sanity. Resources and Links: Connect with Jackie on LinkedInLearn more at People PrinciplesDan Martell’s book: Buy Back Your Time If you enjoyed today’s episode: Subscribe to World’s Greatest Boss wherever you listen to podcastsLeave a review to help more business owners find the showShare this episode with a founder friend who’s overwhelmed and needs help