An Honest Recruiter Told Me Why Most Job Seekers Don’t Get Hired

As someone who has hired hundreds of folks from all walks of life into all kinds of tech startups, I thought I had a handle on how to find the rock stars I needed.

But the recruiting process has changed dramatically over the last few years. Not only has it become harder for talented folks to find a job, the system as it exists today seems to be actively playing defense against recruiting the best person to fill that job.

Look, I’ve worked with recruiters on and off over the last two decades. Some are straight useless, some are excellent, and a few have become friends over the years. As I was writing a recent column about the flood of fake jobs in the system, I had an extended discussion over drinks with one of my closest recruiter friends.

I was looking for secrets. She didn’t have secrets. But she had tough love.

Here’s what “Rosa” told me. These are her top reasons why most job seekers don’t have a shot at finding the job they want. These reasons are not boilerplate. They’re rather eye-opening. And be forewarned, they might hurt.

Your Resume Is Terrible

Shockingly, a lot of very talented people tend to hide their talent in a field of structured, formal, cryptic nonsense.

“I’m looking for white space,” Rosa said, during a discussion about resume first impressions. “If you’ve done important things, you should be able to highlight that in a few short words.”

The converse is also true. If someone has spent their career riding a wave of what was happening around them, that truth will surface in a hyperwordy, buzzword-fueled, over-designed word salad of a resume.

In other words, a lot of words that don’t add up to anything.

The days of a resume as a biography are long over, according to Rosa. Your resume isn’t the snapshot of you as a model employee, it’s an attempt to match qualitative and quantitative aspects of the candidate to the job.

And if you haven’t done a lot of important things yet? Or recently?

“Fine,” she said. “I understand that not every job lets you spread your wings. Your experience is only part of your resume. Make it short and sweet and move on to the next section.”

You Don’t Do Anything Outside Of Work

“You know what your edge is?” Rosa asked me.

“Yeah. Actually. I do. The writing.”

“Exactly.” She pointed at me. “You write about what you do. Constantly, in-depth, and not because you have to for your job. If anyone clicks on your portfolio, it is a big plus in your favor.”

“Although lately it seems I’m trying to hang myself.”

“Doesn’t matter.” She shook her head. “Whether someone agrees with you or not, it shows you are constantly thinking about what makes a company successful.”

I’ve been writing for as long as I’ve been working. It feels like that anyway. But it took me a while to figure out that writing about what I did — and everything that comes with it to make that writing valuable to others — not only boosted the optics of my own value, but also went a long way to making me more valuable at what I do.

If you’re a software developer, you need to show that you’re not just thinking about software development from 9:00 to 5:00 on weekdays. And not just by listing skills or interests or classes. You’ve got to show action that reveals passion and motivation.

“I honestly don’t care if you run marathons or if you’re a good Dad,” Rosa said. “No one does. Those are all nice conversational points, but the odds of hobbies or character traits being the reason you get an interview are nil.”



I said, “It isn’t a college application.” She almost did a spit take, and pointed at me again

You Don’t Do Any Prep

While it’s not terribly surprising how little preparation a candidate might do for an interview, a lot of job seekers don’t realize that preparation starts with the application.

“The move to digital has made job hunting like throwing darts at a dartboard on both sides,” Rosa sighed. “It’s gotten better recently, but the conventional wisdom is still ‘throw 100 applications at the wall and see if one sticks.’”

Unsurprisingly, this doesn’t work.

Real recruiters for real jobs don’t want to play a volume game. And what Rosa told me is that job seekers spend way too much time thinking about themselves and what they have to offer, and precious little time thinking about the company and what it needs.

“Is that fair?” She asked hypothetically. “I don’t know. But it is necessary.”

This goes back to the connection points used to match the resume to the job description. Not only does the resume need to be simple and effective, it needs to be tailored to the job, the role, the company, the industry, even the people at the top of the food chain.

If you can find these connection points, ideally the ones that directly relate to what they’re looking for, documenting those connection points on your resume, the application, or speaking to them in the interview can raise your profile over all the other candidates that don’t do it.

Your Answers Are Pointless

“Let me ask you something else,” Rosa drifted into a new topic. “What makes you good at selling yourself, your products, and your company?”

I thought about this for a second, but the truth came to me pretty quickly, so I went with it.

“You know,” I said. “I’ve been doing this for a long time, and at some point, a while ago, I just stopped giving a shit. Like, I know what I do, I know what I’m doing is valuable and worthwhile. And I know people might not always see that. I guess I’d rather die on my feet than live on my knees.”

She laughed. “That’s exactly what an interview is for, that kind of candor” she said. “OK, maybe not that kind of candor, but I can’t tell you how often I get bullshit answers to straightforward questions. And that’s not just a sign of a lack of confidence, it’s kind of insulting that they think I won’t see through it.”

Huh. Turns out the people on the other side of the table aren’t so different.

It’s Still A Two Way Street

I knew all this, but I didn’t. You know?

Rosa gave me a lot more, a lot of it about expectations and confidence. But my number one takeaway, as I hinted in the previous column, was that despite all the digital transformation and chicanery and frustration, the best path is still the honest path.

It’s still about finding the best candidates for the best jobs.

In fact, at the risk of sounding naive, the path to the dream is not a lot different than the dream itself — doing what you love and getting paid to do it and getting recognition and reward when you do it well.

It’s still achievable, even as it seems to be getting further out of reach. The path remains the same. Be honest, put in the work, and fail and

try again