Remote or In the Office? How to Get the Best From Your Executive Assistant

“Would the founder consider a remote Executive Assistant?” Several brilliant EAs have asked me that this year. It is a fair question, and the honest answer is that it depends less on where the EA sits than on how the founder works.

Where most of my placements sit

The majority of the roles I have placed have been office based. As founders spend more time in the office, many want their EA alongside them. Having worked as an EA both ways, I understand the appeal.

For me, the real benefit of being in the office was context. I was not chasing my principal for an update, trying to catch them between calls, or piecing together what had been agreed after a meeting. I could grab two minutes afterwards, understand what had changed and get things moving. That proximity helped me anticipate, not just react.

The real question is not where, but how

Whether an EA can work remotely is the wrong question. The better question is whether the founder knows how to work with a remote EA. If the answer is yes, remote can work very well. If it is no, it will struggle, however capable the EA.

A founder considering a remote EA should ask themselves:

• Will I share decisions proactively, rather than waiting to be asked?
• Will I protect our check-ins, even when the day gets busy?
• Will my EA hear about a change before they are expected to act on it?

If those answers are uncertain, a remote setup will expose the gaps quickly.

Being in the same building is not the same as being aligned

The same challenge applies in the office. If your EA sits ten feet away but still has to chase you for every decision, proximity has not solved the problem. An EA who is physically close but out of the loop is no better placed than one working from home.

What matters is access: to your decisions, your reasoning and your changing priorities. Some founders create that naturally in person. Others create it through a disciplined rhythm of updates and check-ins. Either can work. Neither happens by accident.

What I ask founders when I scope a role

When I take on a search, I want to understand what the founder actually needs from being together. These are very different conversations:

• “I prefer people in the office.” A preference about culture or habit. Worth being honest about, and worth being clear it is a preference.
• “I need someone alongside me to navigate a constantly changing day.” A functional need. It points to real-time context, quick decisions and a founder whose diary moves by the hour.

Knowing which one it is shapes everything from the job description to the shortlist. It also helps candidates make an honest decision about whether the role will suit them.

Making either setup work

1. Be explicit about expectations. Agree how often you will speak, how decisions will be communicated and what the EA can act on without asking.
2. Protect the check-in. A short, regular touchpoint matters more than long, irregular ones, wherever the EA sits.
3. Share the why, not just the what. Context is what lets an EA anticipate rather than react.
4. Close the loop after meetings. A two-minute debrief, in person or by call, saves hours of piecing things together later.
5. Match the setup to the need. If the day changes constantly, plan for more proximity. If it is steadier, remote or hybrid may work well.

The bottom line

Neither working model automatically makes someone a better EA. But the expectations, communication and access need to match the setup. Get that right and the location becomes a detail. Get it wrong and no amount of office space will fix it.