Good vs Great Executive Assistant: A Founder’s Guide to Hiring the Right EA
You know that feeling when you’re drowning in your inbox at 11 PM, wondering how other founders seem to have their lives together?
Here’s the secret they’re not talking about: they’re not doing it alone. They have executive assistants who manage calendars and think three moves ahead.
But here’s where it gets tricky. Not all executive assistants are created equal. The difference between a good vs great executive assistant isn’t just about experience or skills on paper. It’s about something harder to define but impossible to ignore once you’ve experienced it.
If you’ve ever hired an EA who felt more like another task on your to-do list than a solution to it, you know exactly what we’re talking about. The right EA doesn’t just lighten your load… They multiply your impact.
So what separates the good from the great? After placing hundreds of world-class executive assistants for founders, we’ve noticed some clear patterns. Here’s what we’ve learned about finding that rare EA who becomes your operational secret weapon.
The Mindset Shift That Changes Everything
A good executive assistant executes tasks. A great executive assistant thinks like a founder.
This isn’t about them overstepping boundaries or making decisions they shouldn’t make. It’s about understanding the bigger picture well enough to make your life easier in ways you didn’t even know were possible.
Let’s say you mention in passing that you’re thinking about expanding into a new market. A good EA will put “research new market” on your task list if you ask them to. A great EA will quietly start gathering preliminary data, notice that your biggest competitor just pulled out of that same market, and have a brief on your desk by Thursday morning, without being asked.
The difference is anticipation. Great executive assistants don’t just respond to your current needs; they’re already thinking about what you’ll need next week, next month, next quarter.
The Four Pillars of Executive Assistant Excellence
After analyzing what makes our most successful EA placements thrive, we’ve identified four core areas where great executive assistants consistently outperform:
1. Systems Thinking Over Task Completion
Good EAs are great at completing individual tasks. Great EAs see how those tasks connect to create systems that run without you.
A great EA doesn’t just book your travel; they create a travel system. They know which flights you prefer, which hotels have the meeting rooms you like, and which ground transportation actually shows up on time. They build templates, create checklists, and establish processes that make every future trip smoother than the last.
This systems approach extends to everything: email management, vendor relationships, team communication, and even how they organize your digital files. They’re constantly asking, “How can I make this better for next time?”
2. Communication That Actually Communicates
We’ve all worked with people who send updates that somehow leave you more confused than before. Great executive assistants have mastered the art of useful communication.
They understand the difference between information and insight. Instead of “I called the client,” you get:
“I spoke with Sarah at TechCorp. She’s excited about the proposal but needs to run it by their legal team; she estimates two weeks. I’ve scheduled a follow-up call for the 18th and added a reminder to prepare answers about our data security protocols since that was their main concern last time.”
Great EAs also know when not to communicate. They filter the noise and surface only what actually needs your attention. Your inbox becomes a place of signal, not noise.
3. Problem-Solving That Goes Beyond Google
Anyone can look things up. Great executive assistants think through problems.
When a client meeting gets moved last minute, a good EA will reschedule it. A great EA will reschedule it, check if the change affects your preparation time, notice that you now have a two-hour gap between meetings, and suggest either moving your 3 PM call up or using that time for the quarterly review you’ve been trying to fit in.
They connect dots you didn’t even know existed. They see the second and third-order effects of decisions and changes. Most importantly, they bring you solutions, not just problems.
4. The Ownership Mentality
This might be the most important differentiator. Great executive assistants take ownership of outcomes, not just activities.
If you ask them to “handle the vendor situation,” they don’t just make the phone call and report back. They understand that the real goal is resolving the issue so it doesn’t happen again. They investigate root causes, negotiate solutions, and implement preventive measures.
This ownership mentality shows up in how they prioritize their time, how they make trade-off decisions when you’re unavailable, and how they represent your interests in every interaction.
Signs You Need to Upgrade Your Executive Assistant
Sometimes it’s hard to know if the challenge is your EA or your expectations. Here are some signs that you might need to level up:
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Your EA asks for detailed instructions on tasks they’ve done before. Great EAs build on past experience and improve processes over time.
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You find yourself explaining the same context repeatedly. A great EA remembers not just what you told them, but why it mattered.
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Simple requests turn into long email chains. Great EAs ask clarifying questions upfront and provide complete responses.
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You still feel like you’re managing instead of being supported. A great EA reduces your cognitive load, not adds to it.
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Emergency situations always require your direct involvement. Great EAs can handle crisis management and know when to escalate versus when to resolve independently.
These aren’t necessarily problems with your current EA as a person… They might just need different training, clearer expectations, or better systems. But if these patterns persist despite your efforts, it might be time to consider whether you have the right fit.
What Great Executive Assistants Do Differently
The best executive assistants we’ve placed share some specific habits that set them apart:
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They maintain a “context file” for everything, documenting what happened, why decisions were made, and what to remember next time.
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They think in workflows, not tasks. Instead of “schedule the meeting,” they think “coordinate the decision-making process this meeting is part of.”
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They manage up proactively. They check in on priorities, flag potential issues before they become urgent, and suggest improvements to how you work together.
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They build relationships on your behalf, strengthening your professional network.
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They stay curious about your business, read industry news, and understand your competitive landscape.
The Business Impact of Getting This Right
When founders get the EA decision right, the results compound quickly. Here’s what our most successful clients report:
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Time reclaimed: 15–20 hours per week returned to high-value activities within 90 days.
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Decision quality: Better information and clearer options when making calls.
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Stress reduction: Confidence that someone competent is handling the details.
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Team leverage: Improved communication and coordination across the organization.
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Growth capacity: Bottlenecks removed, enabling faster scaling.
How to Set Your Executive Assistant Up for Success
Finding a great EA is only half the equation. The other half is creating an environment where their talents can shine:
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Be clear about decision-making authority. Define what they can decide independently, what needs consultation, and what requires your approval.
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Share context, not just tasks. Help them understand the why behind requests.
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Invest in their growth. Great EAs want to develop alongside your business.
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Give feedback regularly. Don’t wait for formal reviews.
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Trust the process. It typically takes 60–90 days for a great EA to hit their stride.
The Search Strategy That Actually Works
Most founders approach EA hiring like they’re filling any other role. But great executive assistants require a different search strategy:
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Look for business acumen, not just administrative skills.
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Test for judgment, not just competence.
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Assess cultural fit carefully.
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Check references thoroughly.
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Consider global talent for top candidates at competitive rates.
The Bottom Line
The difference between a good vs great executive assistant isn’t just about getting more tasks done… It’s about fundamentally changing how you operate as a leader. A great EA doesn’t just support your current way of working, they help you evolve into a more effective version of yourself.
If you’re still buried in operational details instead of focusing on growth, the problem isn’t your time management. It’s that you need the right person managing everything else.
Founders who scale successfully aren’t necessarily smarter than everyone else. They recognize that their highest-value activity is finding and empowering great people to multiply their impact. Starting with the right EA might be the single best investment you make this year.
Ready to Hire Your EA?
At Anywhere Talent, we specialize in matching founders with world-class remote executive assistants who go beyond admin to act as strategic partners. Through our rigorous vetting process, we find EAs who anticipate, align, and execute at the highest level, so you can focus on building, scaling, and leading.
