Signs Your Executive Assistant Isn't Working Out (And What to Do)

A founder once told me she'd been quietly redoing her assistant's inbox drafts for two months before she finally admitted it to herself. Every draft technically got the job done, but something about the tone felt off, a little too formal for how she actually talked to clients, and rather than say anything, she just fixed it herself each time. By the time she brought it up, she'd convinced herself the whole hire had been a mistake. It hadn't. She'd just never told her assistant what "off" actually meant.

That's the pattern I see most often. What looks like an assistant "not working out" is frequently a communication gap wearing a bigger costume. Here's how to actually tell the difference between a fixable rough patch and a genuine mismatch, before you make a decision you might regret.

Signs That Are Actually Fixable

They're asking a lot of questions

This one gets misread constantly. A new EA asking clarifying questions isn't a red flag, it's often the opposite. The assistants who quietly guess instead of asking are the ones who cause real problems later. If the questions are thoughtful and specific, that's a good sign, even if it feels like more back-and-forth than you expected.

Their first drafts don't sound like you

Voice-matching takes time and correction, not intuition. If you've never actually flagged specific phrases or tones you don't like, your assistant has no way of knowing. This is almost always solvable with a direct, specific conversation rather than a decision to part ways.

They've missed one thing

One missed deadline or one scheduling slip in the first six weeks isn't a pattern. It's a data point. Everyone, including people who've worked with you for years, will occasionally get something wrong during a period of adjustment.

Signs That Point to a Real Mismatch

You've given the same feedback more than twice

Feedback that doesn't land after two clear conversations usually isn't a communication problem anymore, it's a fit problem. This is different from a new hire needing repetition on a genuinely complex task. If it's a simple, well-explained expectation that still isn't sticking, that's worth taking seriously.

They avoid telling you about mistakes

An assistant who hides a scheduling error rather than flagging it immediately is a much bigger risk than one who makes the error in the first place. Trust and transparency matter more in this role than almost any technical skill, because so much of the job runs on judgment calls you won't see happen in real time.

The relationship feels like managing a task list, not delegating

If you're still writing out step-by-step instructions for recurring tasks months in, rather than describing outcomes and trusting the process, something isn't clicking. A good EA relationship should feel like it's getting lighter over time, not staying at the same weight.

You've started avoiding giving them anything sensitive

If you've quietly decided to keep handling anything confidential or judgment-heavy yourself, and you haven't consciously chosen that boundary, it's worth asking yourself why. That instinct is often your gut noticing something before you've named it out loud.

How to Tell the Difference Before You Decide Anything

Before assuming it's a mismatch, run one honest test: have you given specific, direct feedback, not just a vague sense that something's off, and given it real time to land? Harvard Business Review's research on feedback makes a similar point, vague impressions rarely change behavior the way specific, concrete input does. "The tone in this email felt too formal, here's an example of how I'd have said it" is specific feedback. "Something felt off about that" is not, and it's unfair to judge someone against feedback they never actually received.

If you've given clear, specific feedback at least twice on the same issue and nothing has changed, that's a genuine signal. If you haven't yet had that direct conversation, have it before deciding anything else.

What to Do If It Really Isn't Working

If you've done the above and the mismatch is real, a few things make the transition cleaner:

• Be direct about the specific issue rather than vague about "it's not a fit" (HBR's broader library on giving feedback has good guidance on this), which leaves the person unable to improve for their next role
• Give a defined timeline rather than an abrupt cutoff, if the relationship allows for it
• Document what worked and didn't, so your next onboarding starts from a clearer place instead of repeating the same ambiguity

Frequently Asked Questions

Is it normal to feel frustrated with a new executive assistant in the first month?
Yes, some friction in the first four to six weeks is normal while both sides build shared shorthand. The concern is when that friction hasn't eased by month three.

Should I give feedback before deciding to let an EA go?
Almost always, yes. Many founders never clearly name what's wrong, and an assistant who seems like a poor fit may simply be working from unclear or missing instructions.

What's a fair amount of time to give a new EA before deciding it's not working?
Most working relationships need at least six to eight weeks and one clear round of specific feedback before you can fairly judge whether the fit is genuinely wrong rather than just early.

The Bottom Line

The founder who'd been silently rewriting her assistant's drafts eventually had the conversation she'd been avoiding, and within two weeks the tone issue was gone entirely. Not every rocky start is a sign to move on. But if you've named the problem clearly, more than once, and nothing shifts, that's genuinely useful information, not a failure on either side.