You’re in back-to-back meetings, barely keeping up. Midday, your EA Slacks you a detailed check-in with project updates, reminders, and a few things that need your input. It’s thoughtful. Organized. Proactive. Everything they think you want.
But instead of feeling supported, you feel a little irritated.
You glance at it, sigh, and think, “Why are they sending this right now? I don’t need this much detail.”
That reaction is easy to dismiss as frustration. But often, it’s something deeper. You feel unseen. Misunderstood. Like your EA just doesn’t quite “get it.”
But they are getting it. Just not your version of it.
What you’re experiencing probably isn’t a performance issue. It’s a clarity issue.
And it’s more common than you think.
At Base, we often hear from founders and executives who come to us saying, “My EA isn’t working out.” But when we talk through what’s actually happening, it’s rarely about skill. It’s about unspoken preferences that were mistaken for objective expectations.
Most of the time, these leaders didn’t even realize they had a specific preference. They thought they were easygoing. Low-maintenance. They thought any smart, capable EA would be able to figure it out.
And when that doesn’t happen, the partnership starts to feel off. Trust starts to erode. But not because the EA isn’t trying. It’s because they’re working from a different playbook. And no one has taken the time to compare notes.
When your EA is guessing, no one wins
Your EA isn’t underperforming. They’re under-informed.
Here’s what we often see.
They lean on what worked with a past executive. Maybe that person wanted daily updates first thing in the morning, or highly detailed meeting prep. So your EA does the same, thinking it’s the gold standard. But your expectations are different, and they don’t know that.
They try to read between the lines. Maybe you’ve made a few comments or course corrections here and there. But you haven’t clearly spelled out what success looks like in your world. So they make their best guess, and hope it lands.
They avoid asking too many questions. Not because they’re checked out. But because they want to show you they’re capable. They want to be independent. They don’t want to seem needy.
The problem isn’t effort. It’s context.
Your EA is doing what they believe is helpful. They are trying. Quietly and consistently. But they’re missing key pieces of how you want to be supported, how you prefer to communicate, and what “great” looks like to you.
That doesn’t mean they’re wrong. It just means you haven’t told them what “right” looks like yet.
Misalignment feels like poor performance. But it’s something else.
Many “performance issues” don’t come from lack of effort or even lack of skill. They come from subtle disconnects. Quiet preferences that were never made explicit.
The EA feels like they’re guessing. The leader feels like they’re repeating themselves. Over time, both start to pull back. Communication gets clipped. Trust wears thin. And the partnership never quite finds its rhythm.
It’s not a broken relationship. It’s just one that needs clearer foundations.
Start here: define what “helpful” actually means
If you want to get things back on track, start with communication.
Not just what tool you use or when you get updates. Go deeper. Start with what you mean when you say “helpful” or “prepared” or “on top of it.”
Most breakdowns don’t come from obvious problems. They come from assumptions that never got clarified.
Maybe your EA sends updates throughout the day, thinking they’re staying ahead. But you’d prefer one clean summary at the end of the day.
Maybe they prep a full background brief before every meeting. But you’d rather have two bullets and a reminder of the goal.
Maybe they notice you’re working later and later, missing family dinner more than you’d like. But they hesitate to say something, unsure if it’s their place.
These moments don’t signal that your EA doesn’t “get it.” They signal that you haven’t yet said what “getting it” looks like.
That’s a solvable problem. But it starts with visibility.
Coming next week
We’ll share how to actually have these conversations. How to name your preferences clearly and kindly, without overexplaining or micromanaging.
These conversations don’t have to be long or awkward. They just have to be clear.
