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I hired a ‘combative, controlling and extremely self-centered’ assistant. How do I deal with her — and avoid nightmare hires like this in the future?

Why This Matters

How do I deal with an employee like this who hasn’t technically “done” anything actionable? How do I navigate feeling sorry for someone and hating them (both personally and professionally) at the same...

July 1, 2025
04:48 PM
2 min read
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Advanced ➔ Results Dollar SignsI hired a ‘combative, controlling and extremely self-centered’ assistant. How do I deal with her — and avoid nightmare hires this in the future.

‘The part that really gets under my skin is her intense staring. She’ll lock eyes with you during a conversation and very visibly scan you up and down, even midsentence.

’Published: July 1, 2025 at 12:48 p.

ETResizeListen(10 min)While it is impossible to fully understand a person’s quirks during the span of an interview, you can employ some incisive strategies during the hiring cess to reveal a bit more their character.

Photo: MarketWatch photo illustration/iStockphotoDear Dollar Signs,I desperately need some advice. Last year, I hired a new administrative assistant. Let’s call her Ramona.

Everyone on our team interviewed her, including two (very tough. ) members of our executive team.

She made a strong first impression: articulate, eager and maybe a little down on her luck — which, at the time, I saw as a reason to root for her, not write her off.

We unanimously agreed she was a great fit. Fast forward, and she’s now the source of nearly every point of tension on our team. She’s inconsistent, combative, controlling and extremely self-centered.

Even situations that have nothing to do with her somehow become emotionally charged in her presence.

One colleague, who barely interacts with her, filed a formal-ish complaint simply because of how unsettled Ramona makes her feel.

There are also some strange personal stories she s that leave everyone blinking in disbelief. The Author Aditi ShrikantAditi Shrikant is an advice columnist and personal finance reporter.

Previously, she was a lead reporter at CNBC Make It covering relationships and psychology. Before that, she reported on consumer spending and transportation at Vox.

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