Vicki Bates, CEO, Professional Executive Associates inc.
There's a moment most Executive Assistants know well.
You're sitting across from your executive or on the other end of a Slack message (for our virtual readers!) and you can see exactly what's going wrong. The priorities are scattered and the schedule is working against them. Requests are landing in your inbox half-formed, too late, or without the context you need to act on them. You know what would fix it, but saying so doesn’t always feel like your place to do so.
So you don't. You adapt, you absorb, and you make it work anyway. Or you start looking for another role.
This is one of the most common and least-talked-about tensions in the EA-executive relationship. It is the EA who can see the problem clearly but has no process or standardized method for proposing solutions, due to uncertainty of where their authority lays.
It's certainly not a confidence problem. Most experienced EAs are sharp, perceptive, and entirely capable of holding a difficult conversation. The silence is due to a missing conversation about how an EA can help with strategic planning and direction.
EAs occupy a unique position. You're close to power but not in it. Your effectiveness depends on trust, access, and discretion, which are things that can feel like fragile glass waiting to break. Raising a concern about how the partnership is functioning can feel like overstepping. Like questioning someone who hasn't asked to be questioned.
Add that to the assumption many executives carry, that if something isn't working, they'd already know, and it becomes even harder to introduce the idea that the problem might be structural rather than a one-off.
So EAs absorb this frustration, and executives never get the information they need to lead better.
Nobody wins.
Before you can have the conversation, it helps to name what you're observing. This isn't about frustration; it's about pattern recognition thanks to the unique way an EA can observe. Here are some of the most common signals:
These are clear workflow problems. And most executives, once they see them named and written out plainly, want to fix them.
How to Frame the Conversation
The goal isn't to criticize. It's to make the case for a better working model, with you as a key part of the solution.
A few framing principles that work:
Lead with impact, not frustration. "I think there's an opportunity for me to take more off your plate" lands differently than "I feel like I'm not being used effectively." The first is forward-looking. The second puts the executive on the defensive.
Be specific. Vague feedback is easy to dismiss. Concrete examples like "when X happens, I end up having to Y, which costs us Z" are harder to argue with and easier to act on.
Make it a question, not a verdict. "Would it be useful to look at how we're structuring priorities together?" invites collaboration and shows strategic thinking.
Choose your moment deliberately. Don't have this conversation during a crisis or right after something goes wrong. Find a calm window, be it a regular check-in, or request one specifically. The setting signals the seriousness of the conversation without escalating it.
Executives who operate with strong EA partnerships don't just get more done. They make better decisions, they're less reactive, and they have more cognitive bandwidth for the work that actually requires them.
But that kind of partnership doesn't happen by accident. It requires a functioning feedback loop, including the ability for an EA to say, "this isn't working as well as it could, and here are some ideas to improve it."
Most executives will respond well if the conversation is framed as partnership rather than complaint. They hired you because they needed your support. Helping them understand how to use that support better is part of the job.
The ones who don't respond well? That's useful information too.
Sometimes the friction isn't just about communication style or scheduling habits, it's about structure. The executive doesn't have a clear picture of what they should be delegating, or how, or to whom. The EA doesn't have a clear picture of what the executive actually needs.
That's a harder problem to solve in a single conversation, and a conversation-only approach won't fix it.
This is where a more structured framework can help. PEAS developed the Executive Leverage Framework specifically to diagnose and close that gap. Mapping what an executive is actually spending time on, where the friction lives, and what a high-functioning support model looks like for their specific situation.
If you're an EA who suspects the issue goes deeper than a single conversation, it might be worth exploring whether a more structured approach is what's actually needed.
Learn more about the Executive Leverage Framework
You don't have to wait for your executive to notice the problem. You're positioned to see it first and to bring a solution, not just an observation.
That's not overstepping. That's exactly what a great EA does.
Vicki Bates is the Founder and CEO of PEAS (Professional Executive Associates Inc.)
PEAS helps founders and senior executives build the support structures they need to lead without becoming the bottleneck.