If you want to work with the elite - ignore the career gurus.
Most career advice for Executive Assistants is written by people who have never sat on the hiring side of this market. After a decade placing EAs and Chiefs of Staff with billionaires, UHNW families, and corporate executives on multi-million dollar salaries — I can tell you that the standard advice doesn't just fall short. It actively counts against you. Here's what actually matters.
First, let's define elite. I’m talking about corporate executives on multi-million dollar salaries, billionaires, and UHNW families. People who operate at a level where time is their scarcest resource and the cost of a wrong hire is measured in more than money.
If you're an Executive Assistant or Personal Assistant serious about working at this end of the market, most career advice you'll find online will actively work against you.
They'll tell you to be assertive, disqualify fast, know your worth, never settle. Fine advice for a generic job search. At this end of the market, that approach counts against you. The principals you're trying to reach didn't get where they are by tolerating bravado or performative confidence - and they'll spot it immediately.
Here’s what actually matters, if you’re thinking about breaking into this space.
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These people do not suffer fools or fake confidence. Real confidence goes unsaid. It’s in how you deliver, how you show up, and how you don’t fill every pause with noise.
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Don’t go nuclear in negotiations. Create room for discussion. The person across the table is used to sophisticated counterparties. A rigid opening position signals inexperience, not leverage. There is an ego play to this, be careful.
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Be prepared to shapeshift. Rigidity is a liability at this level. You’re expected to do what’s needed of you, rather than what’s written in a job description. The role will evolve, the demands will shift, and you’ll be expected to move with it - going high and low.
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Be the solution, not the problem. This isn’t unique to this market, but it’s enforced ruthlessly at the top. You’re expected to solve problems, bring solutions to the table, and be thoughtful in your interactions. Problems are friction - remove them as much and as quietly as possible.
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Understand what actually drives these principals. It’s not calendar management, inbox zero, or booking flights. Those are hygiene factors. The EAs who last in these roles understand commercial goals and exactly what is needed to reach them. This is the job.
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Loyalty matters way more than you think. Job hopping is a serious red flag at this level. These people are inviting you into their world. They need to trust you’ll stay and you'll not become a problem for them.
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HR are blockers you must navigate with grace. In most cases, HR/TA are so far removed from these executives on a day-to-day basis, they become a tick box exercise. They do not truly understand the principal's world. Do what you need to pass, and get yourself in front of the Executive in question. Avoid asking questions which may highlight the lack of knowledge the HR/TA professional has regarding the Executive or their world. Build rapport, impress, move on.
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Make it easy to work with you. Be accessible, amenable, and responsive. You’re being judged from the first point of contact - how easy you are to schedule, how quickly you reply, how you’ll make things work on short notice. Work to the principals schedule, do not make them work to yours.
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Their quirks come with the territory. Everyone at this level has quirks, don’t be put off. They didn’t get to the top by being the same as everybody else.
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A revolving door of assistants isn’t always a red flag. Before you write off a role because three people have held it in four years, consider the other explanation: the assistants before you couldn’t keep up. At this level the demand is real and not everyone can sustain it. If you think you’re built for it, and are happy to have a target on your back in the first year - make this clear.
- The pace can be relentless, especially in deal environments. This is not to be underestimated. If you're expecting a clean finish at 5pm, or you want to 'shut off' from work during the weekend. Working within these types of environments is probably not for you.
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When you’ve finished your sentence, stop talking. Silence is not a problem to fix.
It’s also important to remember that roles supporting the elite are few and far between - but when they come up, it’s crucial to be prepared and shift your approach versus how you would when interviewing for other roles.
Realistically - you get one shot at opportunities like this. However, once you're in, you're in.