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Jeffrey Zeldman Presents

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Jeffrey Zeldman Presents - Advice for job seekers - Career
L. Jeffrey Zeldman · 2026-03-02 · via Jeffrey Zeldman Presents

I recently heard from an accomplished former colleague who had failed to impress the recruiter evaluating their initial application for an open position. It was a position for which they were more than qualified. So why hadn’t they scored so much as an initial interview?

Turned out the candidate had punted on questions like, “Tell us about a project or piece of work you’re especially proud of, from any point in your career.” Their answers were brief, generalized, and lacking in detail. Without the context that thoughtfully detailed answers would have supplied, their application was easy to pass over.

When I explained this to them, they responded that they’re humble about their accomplishments and don’t like to brag.

Modesty is a becoming trait, but discomfort in talking about yourself can prevent you from developing a habit of reflecting on your work as it maps to organizational and customer needs … and that’s a habit that every professional who isn’t independently wealthy should cultivate.

Here is how I advised my colleague:

A DM from “Uncle” Jeffrey

If you get a second chance at that job opportunity, you definitely want to brush up on your ability to tell stories about your career, and you need to let go of that embarrassment about listing your accomplishments.

You need to do that for EVERY opportunity that comes your way, not just [the particular opportunity they’d mentioned].

How Recruiters See it

Don’t think of it as bragging. Think of it as part of a negotiation. You’re telling the company what kind of value they can expect to get out of you in return for the salary and benefits they pay.

Like it or not, you are SELLING your services, and you need to think of it as part of your professional responsibility. It is NOT bragging. It’s as clear and focused and enticing an explanation as you can provide for why this particular company can gain exceptional and specific benefits from your expertise, experience, and confidence. Benefits that map to their customers’ current and future needs.

Not responding in detail sends the message to the recruiter that the candidate doesn’t care very much. Isn’t serious about this particular job. May even be responding to every job ad that crosses their desk, rushing through the answers, and not thinking deeply about why they and this company belong together and can uniquely benefit each other.

LET ME REITERATE

That’s how recruiters see diffident communications that lack detail.

They don’t view it as humility. Okay. It’s humility when a world-famous person does it. Like, if Tim Berners-Lee, in an interview, is kind of humble about inventing the WWW, that’s cool. If Paul McCartney behaves modestly when asked about his decades of musical output, that’s cool. But you and I are not TBL or Paul McCartney. We need to sell ourselves.

For a person the recruiter doesn’t know, this is a pitch. The recruiter is looking for people who truly have the abilities that are needed, can show that they understand the business’s needs and bring EXACTLY the unique combination of skills that will help the business grow, have confidence in their abilities and are not afraid to delve into details.

Delving into details in the application stage tells the recruiter you’ll delve into details when solving complex problems for the company and its customers.

Avoiding those details in the application stage doesn’t read as “this person must be a genius who has accomplished so much, they are simply too humble to talk about it.”

To the recruiter it reads as “This person is not passionate about our organization and this particular job opportunity. I’ll look for someone who gives a damn.”

I’m explaining how recruiters think so you can relax, stop worrying that you’ll be misinterpreted as bragging, and be better prepared for this initial stage of landing the job you really want.

Telling you this because I care. Hope it helps!

LAST WORD

[And reader, if you’re similarly modest and tongue-tied when applying for work, I hope this note helps you, too. ❤️ ]