Building the Foundation: The First 30 Days With Your EA

You created the role description.
You posted the position.
You conducted the interviews.
You picked the best candidate, and they accepted your offer.

So…now what?

Bringing a new Executive Assistant (EA) onboard – whether it’s your first or tenth – is probably going to be a little anxiety-inducing. And that’s okay. After all, you hired this person to help you be better at your job and make your life easier, so it feels like there’s a lot at stake. And your new EA is probably feeling a little nervous, too.

That’s why the first 30 days with your EA are so essential.

It’s one thing to have had a good interview experience during the job search process. It’s quite another to work with someone day-in and day-out. The first time I onboarded an EA, I didn’t really know what I was doing. I wasn’t sure how to build trust and set expectations with my EA. I relied a little on the advice of mentors and other executives in my life to help navigate this uncharted territory but mostly I was winging it!

Now that I’ve gained a little bit more experience, I hope I can offer some helpful advice on building the foundation for a successful Executive-EA partnership.

The First 30 Days

While I’d love to give you an easy-to-follow blueprint that perfectly matches our first 30 days working together, the truth is that there’s a lot my EA and I wished we’d done during the early days of our working relationship. But, as the saying goes, experience is the best teacher, so here are our recommendations for the first few weeks working with your EA.

Time. Time. Time.

You’ve probably had a couple of conversations (or interviews) with your EA as a job candidate prior to their first day of work, but you haven’t yet had any in-depth and comprehensive meetings about the company, the role, and how the two of you are going to work together.

Ultimately, you can’t spend too much time together during the first week, and you should try to carve an hour or two out a day – I prefer the mornings – to get acquainted with one another and the new role.

Company Onboarding

The goals of these first few meetings should be simple, but structured. You want your new EA to have a firm grasp of the past, present, and future goals of your company, the organizational structure, and any relevant pain points. It’s like traditional onboarding but with a much higher emphasis on executive projects and strategy. A good rule of thumb is simply onboard your EA as you would any other direct report in your C-Suite.

Set workplace and professional expectations early.

During the interview stage, you probably talked with the candidates about expectations as it pertained to the role description. Generally speaking, I’m guessing this conversation was pretty broad and not that detailed. Now that your EA is on the job, you’re going to need to have a much more robust and in-depth talk about workplace and role expectations. For example, you’ll need to make clear your expectations regarding communication, email management, scheduling meetings, etc. 

And, remember, these conversations shouldn’t be lectures. They’re conversations. Welcome (and encourage) questions from your EA. They’ll undoubtedly have many follow-up questions, and, as the executive, it’s up to you to establish a safe place for those questions to be asked. During these first few days, your EA is learning how to interact with you, and you’re going to want your EA to feel comfortable asking for clarification and more information.

How to deal with me. 

One thing I did that I found effective was I created a “How To Deal With Me” document that listed my pet peeves (ex. “Spending a lot of time reading and responding to emails”), personal motivations (ex. “I like experimenting with change” ) and quirks (ex. “Too much routine stifles my creativity”), and I shared it with my EA during one of our first meetings. We’ll probably talk about this document in a future blog post, but my EA said it was one of the most helpful resources I gave to her when she began working with me.

So, why should this matter? Why am I recommending you make a list like this to share with a new hire? Well, for starters, your EA will work more closely with you than any other employee, so it’s vital they know how best to work with you and your personality. And, perhaps most importantly, your EA is going to discover all of this eventually, so putting it all out there at the beginning will save both of you a lot of time and frustration in the coming weeks and months. Finally, it’s likely your EA has strengths in areas where you have shortcomings, so those insights may encourage your EA to step up in those situations. 

And, after a week or so, I had my EA make her own “How To Deal With Me” document to help me understand her work styles, frustrations, and expectations. It was extremely helpful to compare and contrast our two documents side-by-side and talk through them together!

The building blocks of trust.

As your assistant, your EA will overhear, handle, and act on sensitive information about the company and its employees. And, because of this, you’re going to need to discuss trust as it pertains to confidential material. For example, when I was negotiating the sale of a company where I was the CEO, my EA knew about the negotiations months in advance and had to remain quiet about it to the other associates.

You’re going to need to stress to your EA the value and importance of trust within the context of your working relationship. And even if you’re not planning to directly give your EA much confidential access, your EA is undoubtedly still going to come into contact with a lot of sensitive materials and issues (though I should stress, if you can build trust with your EA to an extent where you can trust them with confidential information, it’s completely worth it. You’re going to need trust if you ever hope to have an effective and efficient working relationship). 

More likely than not, your EA won’t have any trouble with this – it comes with the territory of working with an executive. But it definitely needs to come up in the first few days. And, remember, the expectation of trust cuts both ways. Just as you need to trust your EA, your EA needs to know that you’re trustworthy, as well.  I do not sugar coat the expectations here. I usually say something like, “Breaking trust will cost you your job, so please don’t do something that’ll require me to fire you.”

Let them start.

However, more than anything, I think it’s important to give your new EA some agency and give them an opportunity to jump in during the first few weeks working together. Have your EA organize your inbox, structure your calendar, or write a few emails for you. If you don’t like something, go back and change it and explain why you prefer it one way or another. Give them the freedom to make mistakes and learn from experience. You and your EA will have plenty of time to iron out the details. Instead of aiming for perfection, use your first thirty days to build trust, set expectations, and establish your working relationship.


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