Professional wearing headphones taking notes at a laptop during remote training, illustrating how to train your EA to think like a COO; strategic executive assistant; remote executive assistant.

How to Train Your EA to Think Like a COO

ByAnywhere Talent

Most founders think of an executive assistant as an efficiency tool. A calendar manager, a travel booker, or a meeting scheduler.

But the smartest founders know an EA can be so much more. Given the right training, systems, and mentorship… An EA can start thinking and acting like a Chief Operating Officer, but it all depends on one key factor, which is how to train your EA effectively..

And that’s when everything changes.

How to Train Your EA: From Tasks to Outcomes

In this guide, you’ll learn exactly how to train your EA to think and act like a COO.

Because instead of just helping you manage the day, they help you run the business. They don’t just take tasks off your plate… They make the plate bigger.

In this blog post, we’ll cover:

  • Why thinking like a COO makes your EA exponentially more valuable

  • How to shift your EA from “task executor” to “strategic operator”

  • The mindset, systems, and tools that create COO-level thinking

  • How Anywhere Talent helps founders unlock this transformation

Why This Shift Matters

A COO isn’t just an “operations person.” They’re the founder’s second brain… The person who sees both the big picture and the tiny details, and connects them in real time. When you know how to train your EA for strategic thinking, they anticipate needs and protect your focus.

When your EA adopts this mindset, they:

  • Anticipate business needs before you do

  • Spot inefficiencies you’ve gotten used to

  • Protect your time by filtering what matters from what’s noise

  • Coordinate across teams so execution is frictionless; the difference is dramatic:

A regular EA manages your inbox. A COO-minded EA manages the flow of decisions that shape your business.

Step 1: Shift the Context From “Tasks” to “Outcomes”

Most EAs are trained to ask: “What needs to be done?”
COO-level EAs ask: “What’s the goal, and what’s the best way to achieve it?”

Example:
Instead of just booking a meeting when you ask, a COO-minded EA will ask:

  • Does this meeting need to happen at all?

  • Who needs to be in it?

  • What’s the intended outcome?

  • Is there a faster way to get there?

How to train this:

  • In your weekly syncs, explain why you’re making certain decisions

  • Share the business rationale, not just the task request.

  • Encourage them to challenge the method if they see a better route.

Step 2: Teach Them the Business

A core part of how to train your EA is giving them the business model, metrics, and customer journey. An EA can’t think like a COO if they don’t understand your company’s ecosystem.

That means giving them:

  • Your business model… how you make money

  • Your strategic priorities for the quarter and year

  • Your key metrics (and what they mean)

  • The customer journey from first touch to renewal

Once they see the full map, they can:

  • Prioritize the right opportunities

  • Spot risks early

  • Align their day-to-day work with revenue-driving goals

Pro Tip: Add them to the leadership team’s weekly meeting, even as a silent observer. The context they’ll pick up is priceless.

Step 3: Involve Them in Decision Flows

If you’re mapping how to train your executive assistant on decisions, start with low‑risk calls and expand.

COOs aren’t just executors… They’re decision filters. They know which calls to make themselves, and which ones to escalate.

To train this in your EA:

  1. Give them decision rights in low-risk areas first (vendor selection under $500, meeting scheduling conflicts, follow-up prioritization).

  2. Review their choices, but don’t override unless necessary.

  3. Gradually expand their scope into higher-impact calls.

Over time, they’ll develop your “decision DNA” and start making choices as you would, even when you’re not around.

Step 4: Equip Them With COO Tools

The best remote executive assistants don’t just use email and Slack.
They run on the same operational tech stack as top COOs.

Recommended tools:

ClickUp / Asana / Notion
Project and task visibility

Airtable
Database-style tracking for vendors, clients, and assets

Slack + AI integrations
Quick context access and updates

Loom
Async decision briefs and updates

Google Workspace
Shared calendars, docs, and reporting

Don’t just give them access…  Train them in how you use each tool so they can align with your operating rhythm.

Step 5: Build a Proactive Culture

A COO-minded EA doesn’t wait to be told what to do… They see what’s coming.

You can train this by:

  • Asking them to bring three potential issues to each check-in

  • Encouraging “solution-first” thinking (always pair a problem with a proposed fix)

  • Giving recognition when they prevent issues, not just when they complete tasks

The more you reward proactive thinking, the more it becomes their default mode.

Step 6: Give Them Access to Your Network

One of the COO’s hidden superpowers is relationship management. They know who to call to solve a problem in minutes.

Train your EA to think this way by:

  • Introducing them to key clients, vendors, and partners

  • Letting them handle certain relationship touchpoints on your behalf

  • Empowering them to reach out directly when timelines or priorities are at risk

Over time, they’ll be able to manage key relationships without you… A hallmark of COO-level trust.

Step 7: Use AI as a Leverage Multiplier

In an AI-first world, COO-minded EAs are masters at blending automation with judgment.

Practical examples:

  • Using AI to draft proposals, then refining for nuance and brand ton

  • Running AI-driven market research, but validating the data before you see it

  • Automating repetitive workflows in ClickUp or Airtable so nothing slips through

This isn’t about replacing them. It’s about giving them more capacity for strategic work.

The Transformation in Practice

Here’s how this looks for founders we’ve worked with at Anywhere Talent:

Before After
EA is in reactive mode, completing assigned tasks EA manages the founder’s priorities like a portfolio, advancing, delaying, or dropping based on impact
The founder spends hours each week making small operational calls EA filters and handles 80% of calls, escalating only the top 20%
EA manages the calendar EA manages the energy flow of the week—balancing deep work, meetings, and recovery time


The ROI of a COO-Minded EA

When your EA starts operating at this level, you get:

  • More founder bandwidth for strategic growth

  • Faster execution with fewer bottlenecks

  • Better decision-making through filtered, context-rich insights

  • Higher team alignment because priorities are clearly communicated and enforced

In other words, your EA stops being “support” and becomes “leadership.”

Final Thoughts

This is a training investment, not a title change…

Not every EA will want or be able to make the leap to COO-level thinking. But for the ones who do, the impact is exponential.

The key is to invest early, in context, trust, decision rights, and tools.

And when your executive assistant starts thinking like a COO, you get more than leverage. You get a true operational partner.

Ready to find and train an EA who can become your strategic right hand?

At Anywhere Talent, we match founders with world-class remote executive assistants and help you train them to operate at the COO level from day one.

Let’s find your next business-changing hire.

Book your discovery call today

Similar Posts