Why hasn’t anyone made it easier to get a job?

Is it impossible? Or have people just not tried hard enough?

Hey there informational interviewers,

So I did a DEEP dive on alternatives to informational interviewing this week. Basically I wanted to figure out if there is a better way to get a job (or hire someone!). TLDR: there’s not. Yet.

Feel free to correct me if I’m wrong. Have you found a platform or tool that makes it truly, substantively easier to get a job and that obviates the need for informational interviewing? I would love to know!

Anyways, hang in there everybody. And if you need a little extra support for the journey, join us on Slack. We’re having fun.

Stay Savvy,


Why hasn’t anyone made it easier to get a job?

The central premise of this newsletter is that informational interviewing is the best and most efficient way for job seekers to get jobs and that currently there is no better or more efficient “hack” for securing employment.

I believe this but I also find it perplexing. In 2011 Marc Andreessen famously predicted that software would eat the world. And he was right. Software mediates everything we do: communication, transportation, dating, traveling, consuming and producing media, shopping. The list goes on.

And of course, software—it feels quaint to even talk about software as if it isn’t always-already the water we swim in—does in fact mediate everything about the job search experience, too. Most of the jobs that readers of this newsletter want involve working on or with software. And as job seekers we use software to e-mail employers, research companies, gather information about opportunities, showcase our talents and skills, and proceed through a hiring process.

That’s a big change from the way things used to be. I read a click-bait article recently about how hiring has changed in the last fifty years. Apparently in the 70’s it was common to list your height and weight on your resume, and jobs often stipulated a preferred gender for the applicant. The article also said you had to walk into the office of the place you wanted to work and submit a hardcopy of typewriter-written resume. And apparently, since personal printers didn’t really exist, you had to re-type your resume on a typewriter for every job you wanted to apply to. Oh, and also, most job openings were listed in the newspaper.

That all sound very old-fashioned and time-consuming to me, but whatever, people back then just didn’t have the tools we have now. Still, I can’t help but think it’s not that different from what we do today. The medium has changed (i.e. PDFs not typewriter resumes), but the basic mechanisms of finding a job are the same. We’re still just scurrying around, resume in hand, trying to locate people who might be interested in hiring us and then convince them to hire us. I wish we had universal basic income. Sigh.

But seriously, it’s very strange that almost nothing about this process has been optimized. In fact, some might say it’s actually gotten worse. Yes, I know it’s cool that somethings have improved like it’s now illegal to discriminate against certain constituencies. But the basic experience of trying to get a job may actually have gotten harder.

For example, in theory job boards should make it easier for job seekers to find tons of opportunities. Instead of just seeing a handful of opportunities printed in the newspaper, you should benefit from access to literally thousands of opportunities in your region and around the world. And in some ways these mega job boards have created unprecedented visibility. And yes, people waste hours (and days and weeks and months) combing through thousands of job listings, clicking “apply” and firing off resumes all the while many of the jobs posted are not even real, and are instead just ghost listings that employers or job boards haven’t bothered to take down. It’s as if job seekers are window shoppers now with their nose pressed up against the glass, and the brightly-colored goods are a often just a mirage. For a particularly biting account of the frustrations of this style of job searching see this diatribe.

True, there have been some attempts to move outside the job boards model. Back in the 2010’s there were a bunch of startups that tried to make “Tinder-for-Jobs” happen (see Switch and Jobr, both now defunct). Basically they ran into a similar problem that we have with job boards today. There was a deluge of candidates and deluge of opportunities, and they never figured out a good way to match the right candidate with the right opportunity.

Here’s what one user of a “Tinder-for-Jobs” type tool had to say about the experience on Reddit in 2015:

“The value I get out of a recruiter is that I can talk to them about the position I have open, and what sort of person I’m looking for to fill it. I can do that in human terms, and I work with very good recruiters who understand what we do and what sort of candidate I’m after. Then pretty much every cv that I get sent is somebody that I want to interview. This saves me countless hours. I have yet to find any automated system that is capable of filtering to the point where I wanted to interview every candidate it presents, I‘ll keep trying them though a) cause I’m a sucker for punishment, and b) cause I’d love to find one that worked.”

Eight years later, not much has changed. Hiring managers are still using humans to do the slow, inefficient, in-person work of evaluating candidates. And all of the tools that have been created in the job searching and recruiting space basically just help humans do this work more efficiently. But nothing has been able to replace it.

At tech companies and startup there is this idea that hiring is a sign of failure. If you have hire a new person at your company it means you couldn’t build a good enough process or tool to automate the work or make it easy for your existing employees to do. Obviously thats not 100% true, sometimes you really do need to hire. But I think in some ways we can think of the existence of recruiters as indicative of the failure of technologists to figure out a better way.

Why have technologists failed to replace recruiters? I can think of two possible reasons.

  1. It’s not possible. The fundamental person-to-person nature of hiring and employment will resist all attempts to automate or improve through technology.

  2. Firms got lazy on the advertising model. Job boards and job matching services (like Tinder-for-Jobs apps) are all basically running on an ad model. That model incentivizes the businesses to not help you get a job, and not to help employers find an employee. The just want you to spend more time searching, and scrolling and clicking on their site so they can sell more advertising. Ergo they do not put in the effort to devise a real solution.

Of course there is the third possibility, which is that we’ve just been waiting for AI and that AI will solve everything or disrupt everything into oblivion such that this problem is no longer relevant. I can’t speak to this particular possibility. The signal to noise ratio on AI is whacked right now.

Thank you for reading The Art of the Informational Interview. This post free, but one way you can support my work is by sharing it with your friends, family and colleagues.


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