Most EA Relationships Don’t Fail Because of Fit. They Fail Because of Context.

One of the most common mistakes leaders make when bringing on an Executive Assistant is assuming the relationship should be effective almost immediately, with very little investment on their end.

I understand why this happens. Either they’ve had a great assistant before and forgotten that the level of trust and support they valued takes time to build, or they believe handing off a playbook is the answer.

And right now, playbooks are everywhere. They’re often positioned as the solution for quickly and efficiently onboarding an EA. A playbook has its place. But a playbook is a resource that tells someone what to do. It doesn’t help them understand how you think, the rationale behind your decisions, what you’re trying to build, your goals, or your priorities.

That kind of context can’t simply be handed over in a playbook. It has to be shared, explained, and built over time. Without context, even a highly capable EA is forced to operate in the dark.

And when that investment isn’t made, frustration can build on both sides, and it can look a lot like the wrong hire.

What the Gap Actually Looks Like

Here’s something I see often in my EA groups: an executive brings on a strong EA, hands them a job description and maybe a few logins, and expects things to click within weeks. When they don’t, and responses aren’t quite right, priorities are misaligned, or proactivity feels lacking, the assumption is that the EA isn’t experienced enough or just isn’t the right fit.

But upon closer look, the assistant was never given enough context to make sound judgments. They understood the tasks. They didn’t understand the thinking behind them, which would empower them to take ownership.

That’s not a talent problem. That’s an information problem. For example, if your EA doesn’t know which clients you prioritize or how you respond to emails when everything is urgent, they can’t make decisions in a way that reflects your judgment.

Why This Is Worth Pausing On

If you’ve hired an experienced EA and you genuinely enjoy working with them (this is just as important as their skill set), it’s worth asking a few honest questions before drawing any conclusions.

• Do they understand how you make decisions, or only the tasks in front of them?
• Have you made your priorities clear, including when they shift?
• Have you explained what ownership should look like in this role?
• Have you empowered them to use their judgment, ask better questions, and fully step into the partnership you envisioned for this role?

The strongest EA relationships aren’t built on speed. They’re built on trust, clarity, and shared context.

An EA has no agenda other than working entirely in your interest. But to do that well, they need the right level of context, access, and trust. And when they have those three things, you build a partnership that lets you release the work that doesn’t require your involvement, confident that it will be handled the way you’d expect.

If you work with an EA or are thinking about bringing one on, that investment is where the relationship either takes root or falls short.