How to train: You don’t need a clone. You need alignment.
Most founders wait too long to delegate truly.
Not because they don’t trust their EAs’ abilities, but because they think:
“They just don’t think the way I do.”
“If I hand this off, I’ll just have to fix it later.”
“No one else sees the big picture the way I do.”
Here’s the truth:
Your EA can start thinking like you. But only if you train them to.
This isn’t about handing over a checklist. It’s about teaching someone how to make decisions on your behalf and giving them the context to do it confidently.
Here’s how to do it.
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Start by explaining the why, not just the what.
A to-do list is helpful. But it’s limited.
So, to grow with you, your EA needs to understand why each task matters.
- Why does this email get a personal reply?
- Why does that client always need a Friday check-in?
- Why did you decline that meeting even though it looked important?
When they see the reasoning behind your actions, they start to internalize your values. And that’s the first step toward real alignment.
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Think in principles, not preferences.
Founders often assume their brain is “too messy to explain.” But it’s not. It’s just full of unspoken rules.
Your EA doesn’t need a detailed manual. They need your principles.
For example:
- “We always respond to customers within 24 hours, even if we don’t have a solution yet.”
- “I never take meetings before 10 AM – that’s deep work time.”
- “If someone’s vague in a request, we get clarity before saying yes.”
Start capturing those invisible rules. Write them down, talk them out, and build a shared language.
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Narrate your decisions out loud (at first).
In the early weeks, think of yourself as a coach. Whenever you make a judgment call, narrate it.
- “I’m pushing this meeting because I need more prep time.”
- “I’m sending this short message instead of a long one because this client prefers brevity.”
- “I’m not jumping on this task because it’s urgent for them, but not important for us.”
When your EA hears your reasoning and thought process in real-time, they learn much faster than they ever could from a training manual. This helps you discover how to train them more effectively.
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Give them micro-decisions to practice.
Don’t wait until they’re “ready” to delegate decision-making. Instead, start small and build trust.
Let them decide:
- How to respond to low-priority emails
- Whether to accept or decline certain invites
- How to word calendar notes or team messages
- What to surface in your daily briefing
And when they make a choice, talk about it. Celebrate what went right and adjust what didn’t. You’re building not just execution skills, but judgment.
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Build feedback into your weekly rhythm.
Your EA will never think like you if you never tell them how they’re doing.
Create space every week for intentional feedback. Keep it specific and low-pressure:
- “Loved how you flagged that issue early — that’s exactly what I need.”
- “Next time, let’s hold that meeting for later in the week. Here’s why.”
- “I would’ve replied a bit differently there. Want to walk through it together?”
Consistent, kind feedback isn’t micromanagement. It’s how you shape shared judgment over time.
6. Encourage ownership, not perfection.
Your EA will get things wrong. That’s not a failure… that’s the path.
What matters most is their mindset:
- Do they take initiative?
- Do they ask the right questions?
- Do they care about the outcome as much as you do?
When you signal that ownership matters more than perfection, you create the psychological safety that turns assistants into trusted partners.
Final Thoughts: It’s a Relationship, Not a Task List
The best founder–EA relationships are built over time. They grow through trust, feedback, and a shared commitment to thinking together.
It takes some upfront work. However, once your EA can anticipate your decisions, rather than just react to your requests, everything changes.
You stop managing tasks and start gaining leverage.
That’s when the real scale begins
