Tell me about a time when the job hiring process was broken.

It's been a few weeks since I published my first book - The 5-Step Job Search. I feel happy about the milestone and how the book has been received. But I have to admit that I also feel conflicted about writing a book on the topic of job searching.

I was confident it was needed and would be helpful - that isn't the problem. I feel conflicted because it's a band-aid to succeed in an inherently broken system that I have come to despise, despite being reasonably good at it.

I'd much rather prefer if we can fix the system. I'd much rather prefer if we made the system perfectly meritocratic so that everyone can just focus on being good at their jobs and be magically placed in the right job for them, rather than spending even an ounce of energy in learning to be good at this bizarre skill of job searching.

But that’s just wishful thinking. 

Proxy games


The world is crowded and noisy. Most of us suck at knowing what we want and filtering signals from noise, be it in dating, investing, or hiring. So we invent or blindly accept little games and proxies that help us confidently make not-terrible decisions.

When I was pitching to VCs recently, a friend advised me that fundraising is a different game than building a company - you need to be able to do it, but it isn't a reflection of your ability as a founder. Job searching is similar.

The resumes are screened and selected, implicitly or explicitly, for some desirable phrases, pedigrees, and unverifiable and definitely inflated achievements. We have only recently acknowledged and grown past the blatant gender and race biases in this process, but plenty of others remain strong. If you don't come through a referral, your resume will probably never get past a poorly functioning AI to a human eye.

The interviews are mostly standardized questions that are now freely available in Leetcode, Glassdoor, Blind, or Exponent (along with answers if you upgrade). Most prepared candidates parrot their answers with the standardized CIRCLE, STAR, or IMROBOT frameworks that they have learned and practiced a hundred times. They perfectly match the standardized assessment rubric but bear little resemblance to how the job is done. Beware of trying to solve a problem on the spot like you would in real life, or being creative or nuanced because you will run out of time and your answers won't fit into the neat little rubric the interviewer has to submit.

And let's not forget the creative story-telling round where you narrate unverifiable stories about odd situations conjured by the interviewer - also called the leadership and behavioral interviews. The assessment criteria are a mystery to both you and the interviewer alike, but the general rule is to keep them easy to follow, engaging, and always climax with you as the wise savior. Of course, keep it authentic, but not so naively that you come across as a regular human doing a regular job. That'd raise all sorts of red flags. Again, do not try to wing this - rehearse various versions of all stories for all possible situations, or you will lose out to the other candidates with a more impressive script or delivery.

The hiring process has become so standardized and mechanical that it's fallen victim to Goodhart's Law - “When a measure becomes a target, it ceases to be a good measure". The gap between what it takes to get a job and do the job has grown as much as FIFA on Xbox vs soccer in the field. Hiring processes have come to resemble standardized tests, which are now more a measure of how well you are prepared for them, rather than the required skill set. It isn’t surprising because they were invented by the same kids who loved and aced the standardized tests. Like a good Ivy League application process, they may be okay at identifying the safe and average bets, but eliminate outliers.

How did we get here?

Underlying all these issues is the fact that the vast majority of humans are inherently bad at interviewing and assessing (including those who think they are good), as Daniel Kahneman proved to us. Some forward-thinking companies adapted to this insight and developed a checkbox approach devoid of all human judgment to make not-terrible decisions.

And then there's hubris of how the final decisions are made. I have been in several hiring debriefs and decision meetings, and it's astonishing how anyone can randomly shoot decision-altering opinions from their hip, with little evidence or objectivity. As in any polite corporate groupthink setting, most of these are quickly accepted at face value without much debate or challenge. There's really not much rigor, feedback loop, or accountability for the quality of comments or decisions, so it's mostly a silent failure.

So we have developed this not-terrible cookie-cutter system and diligently transplanted it across all companies sparing little critical thought to revisit or refine it over the years. And like every system, it has been gamed and outdated to the point it is no longer useful. Today many of us see and loathe the absurdity of this system but we helplessly or indifferently continue to play in it.

Is there a better way?

The best way, in my opinion, is for the hiring process to be as close to the real job as possible and over an extended period of time. 

At my startup, when we were trying to hire for a new role, we contracted part-time with a couple of candidates for a couple of months. Through the process, we learned and refined what the role requires and how the candidates performed. At the end of the contract, it was pretty clear who we wanted to hire and it wasn't the one who we'd have picked based on their resume or initial conversations. Of course, there are practical concerns with this approach. You don’t have to do exactly this but explore creative ways to get as close as possible. 

As a company, it is important to introduce accountability into your decision making. This means holding interviewers to a high bar in conducting and assessing the interview, or even requiring the dissenting interviewers to share the news with the candidate, as Boston Consulting Group used to do. 

As a job seeker, you can go out of your way to proactively demonstrate how you'd do the actual job well - through projects, portfolios, and reputation - so that you will be spared from some of the silliness and coin toss of the proxy job search game.