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Interview Framework

HOW TO INTERVIEW AN EA

The questions that reveal character. The signals most principals miss.

01

Tell me about a day when you made a significant decision without being able to reach the person you support. What was the decision and how did you make it?

This question reveals the candidate's decision-making framework under pressure. A strong EA will describe a specific situation with clarity, explain the criteria they used to act, and demonstrate that they understood the boundaries of their authority without needing to be told.

What you are listening for is not the outcome of the decision, but the process. Did they gather available information? Did they consider the principal's known preferences? Did they document what they did and why?

A candidate who cannot recall a specific example, or who describes asking someone else to decide, is signalling that they have not yet operated at the level of autonomy the role requires.

02

What is the thing about how you work that your previous principal valued most. Is that the same thing you value most about yourself?

This is a question about self-awareness and alignment. The gap between what a principal valued and what the EA values about themselves is often where friction lives. An EA who is valued for their discretion but values their creativity will eventually feel unseen.

The most capable EAs have a clear and honest answer to both parts. They know what they are known for, and they have made peace with whether that matches their own sense of identity. That alignment is what makes them sustainable in a demanding role.

Listen for candidates who pause before answering. The pause usually means they are being honest rather than performing.

03

Tell me about a time you were asked to do something you believed was wrong. What did you do?

This question tests integrity and the ability to hold a position without damaging a relationship. The wrong answer is "I just did it." The also-wrong answer is "I refused and reported it immediately." Both suggest an absence of judgment.

The right answer involves a private conversation, a clear articulation of concern, and a willingness to accept the principal's final decision while maintaining their own ethical floor. EAs operate in proximity to power. That proximity requires a clear sense of where the line is.

What this question also reveals is how the candidate talks about a former principal. Discretion in the answer is itself data.

04

Describe the most complex logistical problem you have ever solved. Not the task. The problem underneath the task.

Most candidates will describe a complicated task: a multi-leg international trip, a last-minute event for 200 people. Push past the surface. The task is the symptom. The problem underneath is what reveals capability.

A senior EA will be able to articulate the competing constraints, the stakeholders with conflicting interests, the information that was missing, and the sequence of decisions that resolved the situation. They will describe it with the precision of someone who has thought about it analytically, not just survived it.

This question also reveals how the candidate thinks about complexity. Do they simplify it into a story, or do they hold the full picture? The latter is what you need.

05

What do you need from a principal to do your best work. And what have you learned, sometimes the hard way, that you do not?

This is the question most principals skip, and it is the one that matters most for retention. An EA who cannot articulate what they need is either not self-aware enough or not confident enough to be honest. Neither is what you want.

The second half of the question. What they have learned they do not need. That is where the real information lives. It usually contains a story about a previous relationship that did not work. Listen carefully. You are hearing how they process difficulty and what they have concluded from it.

The best candidates will answer this question with specificity and without blame. They will describe conditions, not complaints. That distinction is everything.

Signals

WHAT TO WATCH FOR THAT MOST PRINCIPALS MISS

Vagueness about decisions

Strong EAs remember specific decisions. Vague answers about "generally handling things" signal a candidate who has not operated with real autonomy.

Loyalty that sounds like dependency

An EA who describes their previous principal in reverential terms without any critical distance may struggle to function when the relationship is imperfect.

Answers that are too clean

Real experience is messy. A candidate whose answers have no friction, no failure, and no ambiguity has either not done the work or is not being honest.

The absence of curiosity about you

A senior EA who asks no questions about how you work, what you value, or what has not worked before is not thinking about fit. They are thinking about the offer.

The questions in this guide are the same ones James uses to assess every candidate before they reach a shortlist. If you'd like us to run the process:

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