James Ketteringham

Ten years placing the people closest to power - Chiefs of Staff, Executive Assistants, and the Office of the CEO - and in some of the most demanding environments in business. This is the place I say what I actually think.

Why Most Executive Assistants Never Progress

Knowing why something is important is the magic ingredient for any elite Executive Assistant


I spend a lot of time thinking about the Executive Assistant profession. For the most part, I try to think beyond the transactional responsibilities we all know.

The potential for this role is absolutely massive. Becoming a genuine force multiplier is how you become indispensable. But most assistants never get anywhere near this level. Not because they can't. Because they never learn to think in the right way. They get so caught up in the surface-level responsibilities of the role, they dismiss the 'why' of their principal's world. 

The number one skill for any Executive Assistant is to truly understand why something is important to their principal. Not in a surface-level "this is important because it's business stuff" sense. In a sophisticated, layered way that most people in this profession frankly don't operate at.

Something like this:

Information comes in to you. You immediately understand which parties are involved and how the information is relevant to each of them. You connect it to what happened last quarter, last week, yesterday. You understand how it might affect your principal. Their mood, their deals, their life. You know the work attached to it and the stakes riding on that work. You know how your principal is likely to react. You know the next steps expected of both of you.

And you act accordingly. Before being asked.

For the best assistants, it's instinct. But the majority of people in EA roles don't process information this way. They wait to be told what matters. They treat every task with the same weight. They don't connect dots across conversations, relationships, or timelines. They operate in isolation when the job demands panoramic thinking.

This gap is enormous.

This type of processing is what takes you from thinking about your task to understanding the entire information tree. Who's involved, who's asking for what, who has leverage, what additional information is needed, who holds it, how this shifts your principal's workload, whether that shift is a problem or an opportunity, and whether any of it is actually a priority right now.

If I could attribute just one 'skillset' to the high-level EAs earning upwards of $250,000 a year - it's exactly this. They know why information is important.

For the assistants who get closer to the top, but end up fired or repositioned within the firm - it's usually because they lack this skillset.

Placing COOs, Chiefs of Staff, Office of the CEO teams, Assistants, and high-level support professionals across financial services, family offices, and technology.

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