Executive assistant CV guides · by Lily Shippen, EA recruiter

Executive assistant cover letter: how to write one I'll actually read

Written by Lily Shippen, founder of the Lily Shippen EA, PA and chief of staff recruitment agency. Thirteen years of shortlisting, tens of thousands of CVs read, and every rule on this page is one I use at my own desk. Who I am

I'll be honest with you about cover letters, because most of the advice out there isn't, and the truth is that when a CV comes through an agency like mine the letter is rarely read, since I've already had the conversation the letter is trying to have. When the application goes direct to a company, a chair, a founder or a family office it's a different story, because the letter is often read first and a bad one stops the CV being opened at all.

So I'd write one when the advert asks for it, when you're applying direct, when you're changing careers into EA work, or when there's something the CV can't explain on its own such as a gap, a relocation or a step down in title for a step up in scope, and otherwise I'd spend the time on the CV instead.

The four paragraphs

1. Why this role, in two sentences. Name the role and give one specific reason it's the one, drawn from the advert or from what you know of the principal or the business, because "I am excited by this opportunity" could open any letter whereas you want something only this application could say.
2. What you run now, at what scale. Say who you support, the size of the business, the diary, the travel, the board cycle and the budget, in three sentences with figures, so that this paragraph becomes your profile, tightened.
3. The one thing that answers their biggest ask. Read the advert for the requirement that matters most to them and then give the single best example from your CV that meets it, with the before and after or the figure, because one example told well beats four told briefly every time.
4. How you work, and the close. Give one or two sentences on the thread through your career and then close plainly with when you're available, how to reach you and that you'd welcome a conversation, rather than "I look forward to hearing from you at your earliest convenience", which nobody has ever said out loud.

A worked example

That's two hundred and twenty words in which every paragraph does its job, there's a figure in nearly every sentence and there's nothing another candidate could have written, and if I were the founder reading it I'd want to meet her.

The lines that get letters binned

• "I am writing to apply for the position of" tells the reader something they already know, so start with something they don't.
• "I am a highly organised, proactive and detail-oriented professional" is in every letter, so it separates nobody, and once the eye skips it the eye starts skipping the rest.
• "I believe my skills are transferable" sends the reader looking for the doubt the moment you say "believe", so show the transfer instead, because the private bank client services manager who ran eight diaries and 200 clients is already doing EA work and should simply say that.
• A second page is something I can promise you nobody reads.
• Repeating the CV misses the point of the letter, which answers one requirement in depth while the CV covers the rest.
• A letter addressed to nobody suggests you didn't look for the name, so find it, and if you genuinely can't then "Dear Hiring Manager" is better than "To whom it may concern", which sounds like the start of a complaint.

Career changers and gaps

If you're moving into EA work from another career, the letter is where you translate, once, in a single sentence along the lines of "I am moving into an executive assistant role because the parts of my job I am best at, managing who gets senior people's time, the judgement calls, the quiet fixing of problems before they are noticed, are the whole of an EA's job", and then you prove it with the example paragraph. There's a full guide to the CV for a career change into EA work.

A gap gets one clause, stated plainly, in the paragraph about what you run now, such as "after three years out to raise my family, I returned in 2025 at the level I left", because employers don't need the gap explained so much as they need to know you're current, and the calm way you say it tells them more than any explanation would.

Match the letter to the CV

The figures in the letter must be the figures on the CV, because I read both and a mismatch is the first thing I notice, since it makes me wonder which one is right. If you write your CV with Margot on this site, she writes the cover letter from the same evidence and angles it at the role you tell her you're going for, so the two can't disagree, and the CV guide covers the document the letter sits in front of.

Lily Shippen

FOUNDER, LILY SHIPPEN, EA, PA AND CHIEF OF STAFF RECRUITMENT · THIRTEEN YEARS PLACING EAS

Lily has read tens of thousands of EA CVs and shortlisted the ones that worked. Margot is her screening interview, written down. About Lily and this site