April 7, 2025
Most founders wait too long to hire an Executive Assistant.
They say, “I’m not ready” while drowning in emails, calendar chaos, and $20/hr tasks.
Your business isn’t stuck because you need to do more. It’s stuck because you won’t let go.
In this article, I will show you the exact playbook to hire your first Executive Assistant.
Ayman's Note: This article is just a preview. I’ve built a full Notion system to help you delegate, onboard, and scale with an Executive Assistant. You can grab that at the end of this article.Know What Kind of Help You Need
Below is the types of Assistants:
- A Virtual Assistant (VA) handles repetitive digital tasks.
- A Personal Assistant (PA) handles errands & home life.
- An Executive Assistant (EA) runs business ops, scheduling, and high-value execution.
If you’re spending 10+ hours a week on admin, you’re losing money by not having an Executive Assistant.
Your focus should be on growth, strategy, and execution—not booking flights or managing your inbox.
Identify What to Delegate
I use a priority system every morning:
A – Must get done today
B – Nice to have
C – Errands/admin
D – Delegate (takes >15 min, doesn’t need to happen today)
If a task is worth less than $100/hr, I shouldn’t be doing it.
Your Executive Assistant should remove friction from your life and business.
- Business tasks: inbox triage, calendar management, travel, scheduling, podcast prep
- Ops tasks: CRM updates, tracking KPI dashboards, SOP documentation
- Special projects: client coordination, event planning, logistics
Find Your EA the Right Way
Forget job boards. Leverage your network.
The best Executive Assistants are already working for great entrepreneurs.
Ask 5 CEOs: “Who’s your Executive Assistant? Do they have any spare hours?”
I found mine through Dan Go.
- Ask 5 founders you trust: “Who’s your Executive Assistant? Do they have extra hours?”
- Get referrals from high-level communities. Most great Executive Assistants come through word-of-mouth.
Test With a Paid Project / Trial Period
Begin with 5–10 hours/week and ramp up as they prove themselves.
Give them real-world tasks like:
- Booking a flight with specific instructions (e.g. under $400)
- Researching competitors
- Creating a summary of a podcast episode
- Drafting an agenda for an upcoming meeting
If they can’t execute small tasks flawlessly, they won’t handle big ones.
If they nail it, increase their hours.
Delegation System
I have a Slack channel called “Ayman Requests.”
Whenever I need something done, I drop it in there.
They own execution so I can stay in my zone of genius.
Not sure what to offload? Use this filter:
- If it takes less than 15 minutes, do it yourself
- If it takes more than 15 minutes and isn’t urgent, delegate
- If it’s worth less than $100 per hour, delegate
Onboard for Speed
Most founders hire an Executive Assistant and expect them to magically figure things out.
Then they get frustrated when mistakes happen.
Your Executive Assistant will only be as good as your onboarding process. Set them up for success from day one.
The first two weeks determine success.
Here’s how to set them up:
- Record a 90-minute Loom explaining your workflow and preferences
- Have them shadow you for a week to learn how you operate
- Start with repeatable tasks, then expand
Correct Mistakes the Right Way
When mistakes inevitably happen:
- Default to trust – Assume the best intentions.
- Use extreme ownership – I reframe mistakes as a failure in my process.
- Correct them
The goal isn’t perfection—it’s continuous improvement.
Here’s how to fix mistakes:
- Small mistake? Send a quick Slack message
- Bigger mistake? Record a Loom video walkthrough
- Recurring mistake? Hop on a call to diagnose patterns
- Still happening? It’s a misalignment—time to part ways
Teach Them to Anticipate Needs
A world-class Executive Assistant doesn’t wait for instructions.
Mine sends me recommendations based on my past actions.
Every month, I ask: What patterns do you notice?
When they start thinking ahead… that’s when you’ve won.
Scale Their Responsibilities Over Time
Once they handle admin, start delegating bigger tasks:
- Event planning
- Podcast research
- Team coordination
The best Executive Assistants grow with you.
Conclusion
Hiring a world-class Executive Assistant isn’t just a productivity hack—it’s a game-changer for your business and peace of mind.
When done right, it unlocks your time, sharpens your focus, and creates space for higher-leverage decisions only you can make.
If you’re making 6-figures without an assistant, YOU are the bottleneck.
Ready to stop being the bottleneck? Click here to find the Notion system for hiring, onboarding, and scaling an Executive Assistant.