A female founder leans back and stretches comfortably at her desk, symbolizing the freedom and leverage gained after successfully completing the first 90 days of onboarding her executive assistant.
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The First 90 Days With Your EA: A Founder’s Playbook

ByAnywhere Talent

How to onboard, train, and build real momentum with your Executive Assistant.

Hiring an Executive Assistant isn’t the end of your workload. It’s the beginning of your leverage. But only if you set things up right.

The first 90 days are everything. Done well, they build trust, rhythm, and results. And done poorly, they lead to disappointment.

Here’s your playbook to make sure it does work out — and pays off for the long haul.

Phase 1: The First 90 Days, Weeks 1–3 — Orientation & Foundation

Goal: Build trust, create context, and start the relationship strong.

Don’t rush into delegation; start with alignment.

This is the time to let your EA inside your world, not just your calendar.

What to Do:

  • Share your systems: Tools, folders, dashboards, SOPs — even if messy.
  • Narrate your day: What you’re prioritizing and why.
  • Explain your principles: What matters to you (and what doesn’t).
  • Review responsibilities: Clarify core focus areas, not just tasks.
  • Build context fast: Let them shadow meetings, listen in on calls, review your inbox or calendar notes.

What Good Looks Like:

  • Your EA understands your communication style.
  • They start drafting, not just asking.
  • They’ve begun to anticipate a few needs without being told.

Phase 2: Weeks 4–6 — Delegation & Trust-Building

Goal: Start handing things off and shape how they run with them.

This is where most founders either over-delegate (without training) or under-delegate (out of hesitation).

Instead, co-create confidence.

What to Do:

  • Give them ownership of 1–2 clear areas
     (i.e., calendar management, meeting prep, inbox triage).
  • Use daily or twice-weekly check-ins to provide feedback.
  • Review their work out loud… explain what worked, and why.
  • Ask how they’d approach something first, then coach them.

What Good Looks Like:

  • Your EA is confidently managing their first domain.
  • You’re spending less time in the weeds.
  • Communication is proactive, not reactive.

Phase 3: Weeks 7–9 — Expansion & Autonomy

Goal: Increase scope and test decision-making muscle.

Now the EA moves from support to leverage.
 You’re not just clearing your plate; you’re growing your capacity.

What to Do:

  • Expand into higher-value tasks: travel booking, project management, team comms.
  • Introduce decision rights: Let them make low-risk decisions, and debrief.
  • Set expectations for daily, weekly, and monthly rhythms (like reporting or prep workflows).
  • Share your calendar and priorities weekly so they can stay ahead of you.

What Good Looks Like:

  • Your EA is owning multiple functions with minimal oversight.
  • They’re coming to you with solutions, not just questions.
  • You feel less in control, but more in sync.

Phase 4: Weeks 10–12 — Integration & Momentum

Goal: Lock in the systems, strengthen the relationship, and plan the next phase.

At this stage, you’ve got someone who knows how you think and makes your life easier every day.

Now, formalize what’s working.
And plant the seeds for what’s next.

What to Do:

  • Hold a 90-day retrospective: What’s working, what needs refining, what’s next?
  • Update roles + responsibilities: Add, clarify, or reallocate as needed.
  • Introduce cross-functional collaboration: Loop them into ops, HR, marketing, and finance.
  • Start grooming them for strategic support: Research, metrics, priorities, prep work.

What Great Looks Like:

  • You’ve stopped saying “Let me do it.”
  • They’ve become your filter, not just your follower.
  • You trust them to speak on your behalf, and they do it well.

Final Thoughts (Why the First 90 Days Matter Most)

Most founders think hiring an EA will save them time. That’s only true if you invest time early on.

The first 90 days aren’t about testing if your EA “gets it.” They’re about teaching, shaping, and aligning, so they can.

Done right, those first three months unlock a partnership that pays dividends for years.

And suddenly, you’re not doing everything anymore.
You’re doing what only you can do.

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