Your New Executive Assistant's First 90 Days: How to Set Them Up to Succeed

Hiring the right Executive Assistant is only half the job. What happens in the first three months decides whether the hire becomes a trusted partner or an expensive disappointment. Most of the difference comes down to how the founder shows up, not how capable the EA is.

Why the first 90 days matter so much

A new EA arrives with no context. They do not know your priorities, your people, your preferences or the unwritten rules of how you work. Everything they learn in the first few weeks shapes the habits of the relationship. If those weeks are chaotic, the pattern tends to stick. If they are structured, the EA can start adding real value quickly.

The aim is simple: move from learning, to doing, to anticipating.

Before they start

• Get the practicalities ready. Equipment, accounts, calendar and inbox access, and the tools they will use, all in place on day one.
• Decide what access you are comfortable with, and when. Trust builds in stages, but be clear about the plan rather than leaving your EA to guess.
• Prepare a short briefing. Your priorities, key people, how you like to work, and what a good week looks like.

Days 1 to 30: learn and listen

The first month is about context. Your EA should be absorbing how you work, who matters and what the business is trying to achieve.

• Walk them through your calendar and explain the reasoning behind how it is structured
• Introduce them to the key people, internally and externally, and explain the relationships
• Let them sit in on meetings where appropriate, so they hear decisions and the thinking behind them
• Hand over a small number of clear tasks and give feedback quickly
• Hold a short daily check-in and a longer weekly review

The most valuable thing you can share in this period is the why. An EA who understands why you made a decision will make better calls when you are not there.

Days 31 to 60: take ownership

By the second month, your EA should be running parts of your day without needing instructions for each step.

• Hand over whole workflows, not just individual tasks: diary management, travel, meeting preparation, follow-ups
• Agree what they can decide alone, what they should recommend and what must come to you
• Ask them to point out what is not working, such as clashing priorities, repeated tasks or gaps in how information reaches them
• Give honest feedback, including on small things, while the habits are still forming

Days 61 to 90: anticipate and improve

The third month is where a good hire starts to become a great one. Instead of reacting to requests, your EA should be spotting what is coming.

• Expect them to prepare for meetings and decisions before they are asked
• Invite them to propose improvements to systems, routines and how you work together
• Review the first three months together: what is working, what to change and where they can take on more
• Agree priorities and goals for the next six months

The mistakes that slow it down

• Handing over everything at once. It overwhelms them and creates rework. Phase the handover.
• Handing over too little. If they are only given simple tasks, they cannot show what they can do and you do not get the leverage you hired for.
• Skipping the check-ins when things get busy. This is precisely when your EA most needs context.
• Saving feedback for a review. Small, regular feedback is far more useful than a verdict at the end.
• Leaving access until they have “earned” it, with no plan. Trust needs a path, not a waiting room.

The bottom line

The first 90 days are an investment. A founder who gives their EA context, clear ownership and regular feedback gets a trusted partner much faster than one who expects them to work it out alone. The best EAs will do a lot of that themselves, but they do their best work when the founder makes it easy.

It is also why I stay involved after a placement. Every EA I place gets three months of hands-on mentoring, because a good start matters for the EA and the founder alike.