What to Ask When You're Hiring Your Next EA (And What the Smart Answers Sound Like)

First: You’re Not Hiring for Task Completion. You’re Hiring for Trust.

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Before we even get to the questions, let’s reset the mindset.

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You’re not hiring someone to manage Outlook. You’re hiring someone to manage you. Your time. Your communication. Your day. Possibly your travel, vendor drama, and inbox triage too.

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That means you need someone who can:

• Read your energy without a meeting.
  
• Filter requests and make judgment calls.
  
• Communicate clearly, early, and without ego.
  
  

These aren’t bullet points on a resume. You find them in conversation.

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1. “Walk me through how you’d manage my day if I gave you full access tomorrow.”

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This is your starting line.

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You’re looking for structure, clarity, and confidence. If they ask about your priorities first? Good sign. If they say “I’d wait to see what you need”? Red flag.

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The best EAs start building a plan before the first login. According to Fast Company, early-stage founders who brought on high-functioning assistants saw better productivity because their EAs built structure fast, not after three weeks of onboarding.

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2. “How do you decide what’s urgent when everything looks urgent?”

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Because welcome to startup life.

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This question tests judgment. You want to hear how they triage, who they loop in, and what they push back on. Do they default to protecting your time? Do they ask for clarification when stakes are unclear?

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According to Gallup, high-performing support staff don’t just follow, they lead when they need to. That starts with decision-making confidence under pressure.

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3. “Tell me about a time you had to manage an executive who was hard to reach.”

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If they laugh? Good. They’ve been there.

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This question reveals emotional intelligence. Look for answers that show ownership without blame. Do they build systems around chaos? Do they communicate upward clearly?

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Burnout often stems from communication debt, not workload. Harvard Business Review points out that broken internal processes (not bad attitudes) are usually the problem. A great EA will spot that before it spirals.

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4. “If you were managing my inbox, what would your system be?”

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Don't just ask if they’ve done it. Ask how they’d do it… for you.

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Listen for systems, filters, labeling, drafts, nudges, snoozes. Bonus points if they ask about your communication style before they answer. The right EA doesn’t just organize, they mirror your brain.

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And here's the data to back it up: According to Clockify, the average executive loses nearly 10 hours per week to email-related admin. That’s a whole day back on your calendar if your EA gets this part right.

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5. “How do you follow up on something when the person hasn’t responded?”

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This shows if they’re persistent, or passive.

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Great EAs don’t wait for replies. They manage nudges, use smart phrasing, and escalate only when needed. They’re not afraid to follow up four times (nicely) until it’s done.

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That kind of “quiet pressure” is what keeps launches on track and deals moving.

Zippia reports that the average EA supports 2-3 executives at once. The ones who do it well? They follow up like pros.

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6. “What’s your approach to handling changing priorities on a daily basis?”

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Because spoiler: your priorities will change.

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If their answer includes words like “flexible” and “re-prioritize,” that’s table stakes. What you want is a clear method, how they track moving targets, how they communicate shifts, and how they protect what's truly important when the whole team is yelling “urgent.”

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This is where tools and workflows come in. If they mention color-coded blocks, Slack etiquette, or automated reminders? You’ve got a contender.

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7. “How do you know when not to bother me?”

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This is the gold question.

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A rockstar EA doesn’t just manage tasks, they manage you. They should know what decisions to hold, what questions to park, and what’s worth a Slack ping at 9:17 AM.

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That level of emotional precision is what separates assistants from strategic partners. It’s how companies build trust that scales. As shared in this RGG blog, founders who delegate with clarity save hours per week, and it all starts with fewer interruptions.

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Bonus Questions to Keep in Your Pocket

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 “How do you like to receive feedback?”
“Have you worked with high-demand personalities?”
“How do you prioritize tasks from multiple stakeholders?”
“What kind of work do you enjoy most in this role?”
“When you’re at your best, what does your executive say about you?”

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What Great Answers Feel Like

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When you’re interviewing, don’t just listen for keywords. Listen for:

• Confidence without ego
  
• Structure without rigidity
  
• Calm energy (you’ll be borrowing it weekly)
  
• Communication that feels like clarity, not chatter
  
  

If they start giving you ideas during the interview? They’re already working with you.

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Still Wondering If It’s Worth It?

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Let’s go back to the numbers.

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• Asana found that 58% of the workday is wasted on admin and follow-up.
  
• Clockify shows execs waste 25% of their time in scheduling hell.
  
• Gallup  links effective delegation to 24% higher productivity.
  
• Fast Company says the best time to hire is before you think you need it.
  
• Forbes calls Executive Assistants “indispensable” for modern leaders.
  

Hiring an EA isn't a perk. It's a smart investment.

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Don’t Waste the Interview

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You’re not hiring for a checklist. You’re hiring for chemistry, clarity, and control of your most valuable resource, your time.

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Ask better questions. Listen for operator energy. And if they start making your life easier before you even send the offer?

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You’ve found your person.

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Want a shortcut?

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We hand-pick, train, and match EAs to founders who are ready to delegate without the resume shuffle.

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