What to Look for When Hiring an Executive Assistant

Hiring an executive assistant is one of the highest-leverage decisions a C-suite leader can make.

Done well, it frees up hours of your week, reduces cognitive load, and gives you a trusted partner who makes the entire operation run more smoothly. Done poorly, it creates more work — the kind that comes from managing someone who isn't actually equipped for the role.

So what should you actually be looking for?

Experience at the right altitude

There's a meaningful difference between an EA who has supported mid-level managers and one who has operated at the C-suite level. The demands are different. The stakes are higher.

The judgment calls are more complex. The discretion required is non-negotiable.

When you're hiring for C-suite support, look for someone who has worked in that environment before — who understands the pace, the pressure, and the level of ownership the role requires. Ask about the most complex situations they've navigated. The answer will tell you a lot.

Proactivity — not just responsiveness

A reactive EA waits to be told what to do. A strategic EA is already working on what you're going to need next. This distinction is everything at the C-suite level, where there simply isn't time to brief someone on every decision.

In an interview, listen for language that signals anticipation — "I noticed," "I flagged," "I took the initiative to." Those aren't just good phrases. They're indicators of how someone actually operates.

Judgment and discretion

Your EA will have access to your calendar, your inbox, your travel, and often your most sensitive communications. They'll be fielding calls from stakeholders, managing relationships with your team, and making decisions on your behalf.

The ability to exercise sound judgment — to know what to handle, what to escalate, and what to keep confidential — is not optional. It's the foundation the entire role is built on. Look for someone who speaks about confidentiality and discretion naturally, not as an afterthought.

Communication that matches yours

A great EA doesn't just communicate well in general — they communicate well in the way you need them to. They learn your voice quickly, represent you accurately in writing, and know when to be brief versus when to give you the full picture.

Ask candidates how they adapt their communication style to different executives. The ones who can answer that question specifically and thoughtfully are the ones who have actually done it.

Ownership over task completion

The best EAs don't just complete tasks — they own outcomes. They follow up without being asked. They close the loop. They notice when something hasn't landed and take responsibility for fixing it. That level of ownership is rare, and it's what separates truly strategic support from capable-but-basic support.

Ask for specific examples of times they took full ownership of a complex situation from start to finish. Then listen for whether they talk about the outcome — or just the steps they took.

A final thought

The right EA isn't just someone who can handle your workload. They're someone who can handle it the way you need it handled — with the judgment, discretion, and ownership that your role demands.

That standard is worth holding out for.

At The Summer Associate, it's the standard we hold ourselves to every day. If you're looking for strategic EA support that actually moves with you — we'd love to connect.