Working for a Rookie Executive: Read This Before You Say Yes

What to know before working for a first-time executive…

Congratulations! You’re an assistant a few years into your career who just landed a job working for a high-energy entrepreneur or executive. You’re beyond excited. This is the chance you’ve been waiting for—the opportunity to step into a fast-paced, high-impact role where your skills can really shine.

The only catch? The executive has never had an assistant before…

At first, that might not sound like a big deal. You’ve been doing your job long enough that you can figure it out together, right? You see this executive as a blank slate—an eager newbie who just needs a little guidance. In your head, you’re thinking: Perfect. I’ll coach them into being the dream boss, and we’ll be unstoppable.

But here’s the truth: working for a “pre-assistant” executive is a completely different game.

It’s not easier. It’s not “just like any other job.” In fact, it’s at least 2–3 times harder than supporting someone who already knows how to work with an assistant.

Why? Because they have no idea what to do with an assistant.

They don’t know what you do, how you do it, or why it matters.

They don’t know what’s worth delegating or how to hand it over.

They don’t understand why you need to book their flights now when they usually just wing it the day before.

They don’t see the ripple effect of ignoring your requests for context.

But it’s not malicious—it’s just naïve ignorance.

Executives who have never had an assistant literally have no frame of reference for the brilliance you bring. They don’t understand that delegation is a skill they have to learn. They don’t know that your obsession with details, timelines, and organization is the thing that will free up 20%–50% of their time.

(Yes, that’s real—studies show executives can free up nearly 8–20 hours a week when they delegate effectively to an EA.)

So if you’re considering taking a role with what I call a “Freshman Exec”—an inexperienced, pre-EA leader—there are a few things you need to know before you sign on.

Tip 1: You Will Be Doing Two Jobs (for 6–24 Months)

When you accept a role with a Freshman Exec, you’re not just signing up to be a stellar EA. You’re also signing up to be a patient, empathetic teacher.

And those are two completely different jobs.

Being a great Executive Assistant means anticipating needs, managing chaos, and keeping everything humming.

Being a teacher means breaking lessons down into digestible chunks, calmly and consistently explaining why something matters, and repeating that lesson six different ways until it finally sticks.

For example: You might know that booking flights two weeks in advance saves money, ensures better seats, and avoids stress. Your exec, who’s always booked last-minute, doesn’t know any of that. They just think you’re being “extra.” So you explain—every time—why this matters until the behavior changes.

That’s the job.

And it’s not a short-term gig. Depending on the person, it may take six months, a year, or even two years before they fully “get it.” During that time, you’ll be balancing execution with education, performance with patience.

If teaching is not in your DNA, if you don’t have the desire to explain the same concept seventeen different ways, this is not the job for you.

Tip 2: Be the Quarterback, Not the Receiver

It’s football season, so let’s use a metaphor…

Even if you’ve never watched a game, I’m sure you know this much: the quarterback runs the show. They call the plays, they decide where the ball goes, and they keep the momentum moving forward.

When you’re working for a seasoned executive who understands the Executive Assistant role, you can afford to be more of a receiver—waiting for the ball and only catching what comes your way.

But with a Freshman Exec? Forget it.

There is no playbook.

There are no clear routes.

There’s no structured delegation.

If you wait around for them to hand you tasks, you’ll be twiddling your thumbs—or worse, getting blamed for dropped balls you never even knew existed.

You have to be the quarterback.

That means proactively managing your own workload. Laying out for them what you can do, what you should do, and what you must do. Showing them the menu of ways an Executive Assistant can support.

Calling the plays instead of waiting to be told.

It might sound uncomfortable at first, but this is how you establish authority and demonstrate value. Otherwise, you’ll always be playing catch-up in a game that has no rules.

Tip 3: Confident Communication Builds the Relationship

Let’s be blunt: you cannot get frustrated with an inexperienced executive for acting… inexperienced.

They have never done this before.

They have no model.

They have no “last EA” to compare you to.

That means you can’t sulk when you don’t get enough context, or stew when they forget to loop you in.

You have to ask questions.

And please, ban this sentence from your vocabulary: “That’s not how my last executive did it.” (It’s nails-on-a-chalkboard for both sides.)

Instead, step up with clear, confident communication:

• If they’re silent, ask for the missing details.

• If they’re vague, get specific.

• If they’re underutilizing you, tell them what you can take off their plate.

• If they’re floundering, suggest a process.
  

The worst thing you can do is retreat into frustration. Passive-aggressiveness kills these relationships faster than anything else.

The Emotional Reality of Working for a Freshman Exec

Let’s talk about the human side.

When you’re supporting someone who has never had an Executive Assistant, you will feel invisible at times.

You’ll wonder why they don’t “get it.”

You’ll feel underappreciated.

You may even question your competence.

You’re not imagining things. This work is harder.

But here’s the flip side: you’re also shaping how this person will think about assistants for the rest of their career.

You’re creating their very first impression of what’s possible. If you do it well, you’re not just helping yourself—you’re helping every EA who comes after you.

That’s powerful.

How to Decide If You’re the Right Fit

Before you take a job with a Freshman Exec, ask yourself honestly:

• Do I have the patience to teach, coach, and repeat myself for months (or years)?

• Am I willing to be the quarterback, not just the receiver?

• Can I communicate with confidence instead of frustration?

• Do I want to shape how this executive views assistants for the rest of their career?
  

If the answer is “yes,” then buckle up—you’re in for a wild ride. It won’t be easy, but it will be one of the most impactful partnerships you’ll ever build.

If the answer is “no,” that’s okay too! There’s nothing wrong with wanting to work with someone who already understands the value of your role. In fact, knowing your limits is one of the smartest career moves you can make.

Final Thought

Working for a Freshman Exec is not for the faint of heart. It requires patience, communication, resilience, and a teaching mindset.

But it also offers the rare opportunity to fundamentally change how one leader views and values Assistants.

So if you’re considering a role like this, go in with your eyes wide open. Understand that you’ll be doing two jobs, calling the plays, and coaching your leader every step of the way.

And remember: you’re not just building their productivity. You’re building their future partnership with every assistant who comes after you. That’s legacy work.