Why I'd rather send five tailored résumés than fifty generic ones
Okay you guys. Last time we pulled words out of a job posting. Today we're talking about why that matters more than volume.
Because I know what a lot of you want to do. You want to fix this résumé once, save it as "Resume Final," and fire it off to every posting you find. Fifty applications this week. Play the numbers.
Honestly, I think that's a waste of your evening.
The math doesn't work the way you think it does
A generic résumé is written to be acceptable to everyone, which means it's compelling to no one. It's aimed at "jobs" in general. Nobody hires for "jobs" in general. They hire for one specific opening with one specific list of problems they need solved, and if your résumé doesn't speak to that particular list, it reads like static to them.
So fifty generic résumés isn't fifty chances. It's one weak résumé sent fifty times.
Five résumés, each one rebuilt around the actual posting, each one using the words we pulled out last lesson — that's five real chances. I'd take that trade every time.
The cover letter thing
I want to tell you about a mistake I made, because it's the cleanest example I've got.
Early on I applied to a job and wrote a cover letter I was genuinely proud of. Two hours on it. I explained my whole background, why I wanted the role, what I could bring, tied it all together nice. Sent it off feeling good about myself.
Nothing. No response at all.
A few weeks later I applied to a job that was almost identical — same field, similar company — and this time I was tired and just wrote three plain sentences. Here's who I am. Here's the two things I've done that match what you need. Here's that I'd like to talk. That's it. No polish.
I got a call the next morning.
That's not a big scientific study, it's one data point from my own spreadsheet. But it matched what I'd already suspected: the person reading these things is busy, and they are not grading you on prose. They're scanning for whether you match. The two-hour version and the ten-minute version did the same job, and the short one actually worked better because it respected their time.
I stopped trusting long cover letters that day. I'm not saying skip them if a posting asks for one. I'm saying stop treating them as your one shot to be eloquent. Save the eloquence. Spend the effort on tailoring the résumé instead, because that's what's actually getting read closely.
What tailoring actually looks like, in practice
This isn't a rewrite from scratch every time. It's targeted.
- Pull up the posting and your list of key words from last time.
- Open your current résumé draft.
- Look at your bullet points and ask: does this line use their language, or my language? If a posting says "cross-functional" and your bullet says "worked with other departments," change your bullet. Same fact, their words.
- Reorder if you need to. If the posting cares most about customer service and your résumé leads with a data project, move the customer service line up. Relevance first.
- Cut anything that doesn't serve this particular posting. You can always put it back for a different application. This is the version for this job.
Fifteen, twenty minutes per résumé once you've got a solid base document. That's the whole cost. It's not fifty more documents, it's one strong document adjusted five ways.
The opinion, plainly
Tailor the résumé to the actual job, not to "jobs." I'd rather send five tailored versions than fifty generic ones. I've done it both ways and the tailored version wins, not close.
If you disagree and want to blast out fifty, that's your call, it's your job search. I just think you're going to be tired and discouraged in two weeks with nothing to show for it, and I'd rather you not waste the energy.
Before next time
Pick one real job posting you actually want — not a random one, one you'd take if they called tomorrow — and bring it with your résumé draft. We're going to tailor it together in class.