Don’t buy the hiring lottery

It’s never easy looking for a job. Trotting through shitty, vague, unrealistic openings that are frequently been written by people thrice removed from those you’ll eventually be working with. Then hoping to hear back from the black hole that is the application process at many companies. Ugh. No wonder many applicants end up jaded, if stuck in that process for too long.

But sitting on the other side of the process can certainly also make you jaded. Reading through hundreds of applications from people who aren’t even trying. Trying to understand the role or trying to express why they’d be a good hire.

I think part of the problem is the idea that “if you don’t apply, you can’t get it!”, which sorta sounds like a “if you don’t play, you can’t win” slogan for a lottery. That’s a perfectly reasonable conclusion from someone who has gone through one too many black-hole application processes, but it’s also wrong.

Sure, you can’t hit if you don’t swing, but it doesn’t matter how many times I swing, I’m not going to hit a homerun against a Yankees pitcher. Not one in a hundred, not one in a thousand. Yes, step one of being in the game is showing up. But unless step two is being somewhat qualified for that game, you’re still going to lose.

This doesn’t invalidate the idea that there are perfectly qualified candidates who hold themselves back from applying due to imposter syndrome or anxiety or other reasons stemming from a lack of confidence. Boosting that confidence amongst the qualified with encouragement is ace. Let’s keep doing that.

But let’s stop pretending that the hiring process is a lottery. That sending out the most resumes is how you win it. That you should apply to positions no matter how remote of a stretch it is, because, hey, they gotta hire someone, and that might as well be you!

Applying for a job is hard. Every time you don’t hear back, you can lose a tiny little something of yourself. You thus might try just that little bit less next time. So if you keep applying for unlikely-to-get jobs, you might eventually water yourself down, and dilute your application, until it’s a very thin cup of tea indeed.

Don’t do that. Apply when you have a real shot. Stretch a little, but not too much. Save yourself and your ego from the lottery trap.

20 thoughts on “Don’t buy the hiring lottery

  1. Did you get more than a few “stretch” applicants for that Director position?

    1. “Names, characters, businesses, places, events, locales, and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental” 😂

    2. I assumed this posting was about the response for the customer support position, but I had forgotten about the marketing position. 🙂

      That being said, even though I’m in education, that customer support position sure does look interesting….

    3. Ryan, the qualifications required for the customer support positions we have open at Basecamp are not at all industry-specific (unlike most other openings at Basecamp!). I’d say someone from education is likely to be an ideal candidate: If you’re patient enough to teach, skilled with writing, and have basic proficiency with computers, you’re not stretching at all 😄

  2. Yo DHH thanks for this. I’ve been feeling the pinch a lot lately from the vague, non-feedback responses from jobs, even ones where recruiters have hit *me* up about, and that’s what I think is most confusing. Of course I’m not really owed anything by a company that tries to hire me, but I’m young (28) at the first few laps of my career and have big ambition, and put a lot of myself into preparing for interviews + any take-home exercises. So it’s a bit jarring and surprising when $BIGCOMPANY ghosts me not unlike how old girls would in high school. I’m still trying as much as I can to apply, remain positive and put my best foot forward, but this culture of entitlement from hiring managers and recruiters is really, really fucking dumb.

  3. Thank you for this article. I am glad to have my feelings supported from the other side of the hiring table.
    I can’t tell you how many recruiters get offended when I tell them “that position looks interesting, but I don’t think it aligns to my skills set”.
    I try very hard to align my goals and skills to the job description at hand, but so many of them are meaningless for all the buzz words and boiler plate language.

  4. Brilliant, and while I have been on both sides of that gate I can realize one thing. The higher you make the fence the greater risk the applicant needs to take on to jump over it. For a “conservative” position that requires both highly technical and verbal skills this is something Basecamp may struggle with. In reading through a recent posting you offered I thought, “Oooo, I do that and that, and that already, that I know I can learn to do and that will be a challenge but perhaps I should apply…”

    So why did I neglect to send in the application? Was it because I felt the process was to arduous? Am I lazy?

    In the end I felt the timing was wrong. The requirements were laid out in a way that made me realize, while I met them, I didn’t have the time to put in the work needed to create a proper application that would make it past initial inspection.

    So you have one less…

    1. That seems like a good outcome for both parties! If you don’t have the time/energy/inclination to write a compelling job application, it would surely be a waste of time sending off a lackluster one, just because. The person on the other side can’t know that you’re really that much more appealing of a candidate than your application lets on. So putting in less than the full effort seems like it would waste both your time and the time of the reviewer.

      The right job at the wrong time is as grand of a reason to pass as the right candidate at the wrong time would be.

  5. I have the luxury of applying for jobs while in full employment so haven’t been jaded by rejections and nonreplies.

    Despite that, I couldn’t help feeling anxious reading through this post as if you were specifically talking to me about my Customer Support application.

    (Talk about an unchecked ego)

  6. “…the idea that there are perfectly qualified candidates who hold themselves back from applying due to imposter syndrome or anxiety or other reasons stemming from a lack of confidence.”

    This has been me for the past years! The stars must’ve aligned at the moment I read about the Customer Support position though, because I *knew* right then, “that is for me, and I am for it!” It’s been a long time since I’ve felt the pull of the universe so strongly and I’m pretty excited to submit my story for consideration; scary as it may be to put myself out there and face the possible rejection.

    For anyone out there holding themselves back, I hope that you, too, find that one place that speaks to you, and at a time when you are listening, and that you find the courage to not let it pass you by. Such providence is not to be trifled with.

    Even if this shouldn’t play out, there may be something about the experience that triggers the next chain of events that will lead me to (hopefully/finally) where I’m supposed to be. There’s no reason not to try. Good luck, everyone.

  7. Hey David, I had this idea long time ago: why you don’t create software resume under the different name and apply to jobs in Silicon Valley? I am Senior Software Engineer, Ruby/Rails and other web technologies, and I often don’t even hear back and get rejections saying I’m not good enough. Apply to tech giants and to startups, and see how they treat you. Then make a post to reveal the truth! You’ll be surprised how it works and how everything is broken!

  8. I’ve had applying for Head of Marketing top of mind. With three days until the deadline I fortuitously find this blog.

    Two additional issues with job search:

    1) When a job posting is 3-4 months old, how much of these positions are vanity for investors, and to generate awareness? I’ve seen two productivity software platforms with 3 different product marketing positions open for 3+ months.

    And of course they are growing like crazy. The videos by HR are ra ra about culture and produced in 4k. But when you go to their homepage, the first video you see is some product manager giving a technical feature-heavy walkthrough of the product.

    Please, amateur hour video gets no one excited. No contrast. No vision. No business case. Means no conversions and low growth in the new world of product-led software. Hard to hire for 3 marketers when you can’t get the first one right!

    2) If you’ve been busy starting tech companies, raised capital, but didn’t have a major exit…expect many months to find employment. In my case I’ve had nearly two years as a contractor.

    Happy hunting, and great post.

    1. I know of one company that continuously advertises their positions (even if they are filled), then files away the promising looking resumes and only contacts those people if there’s a sudden vacancy. That’s another reason for those “old” postings.

      I’ve had the “pleasure” of sitting on both sides of the table when it comes to job hunting. There’s nothing more fun than being told by the highers-up that you HAVE to interview a candidate who doesn’t even have the certifications your customer requires, and when you interview them for a networking position, they don’t even know what a three-way TCP handshake is. Sigh.

  9. I agree you should think twice about applying for jobs that you hold zero qualifications for – no use wasting everyone’s time.

    Playing devil’s advocate though, I think some companies can focus too much on the years and accomplishments listed,and not enough on the drive and creativity of the applicant. Those skills are hard to convey on a piece of paper, so the hiring manager is taking a risk when they extend an interview to candidates on this end of the spectrum, but I think it has the potential to pay off.

    Sometimes they are a better fit because they have confidence in their skills and are dedicated to proving they can get the job done.

    So to those thinking about taking taking the leap, I say jump!

  10. David –

    What a great way to make some observations, posting this blog on the heels of the positions just posted at Basecamp. You can almost see all the nerves rattling just reading these comments; of which I am not exempt.

    I started my journey to work remotely about a year ago. I have been in the “application black hole” many, many times (so depressing), but to keep up a good attitude and my customer service edge; I found some fun temporary work. I paid some bills while I worked at UGG for the holidays; whew….slippers and boots for everyone!! It was exhausting and rewarding at the same time, it reminded me why I like an office job!! The customers were great, it was all the standing and running around that was hard (and shoplifters – they were horrible)!! I still work with customers daily; just not with slippers, or boots!!

    What I have truly come to appreciate are the companies that ask questions, like you have at Basecamp, for your application process. Those are the companies that have pushed me to learn more about myself. While every company will need to know our history (dates, addresses, where, bla, bla, bla – those are just facts; CV/Resumes while necessary are boring). To really see who you might be choosing as your next candidate, you need to ask some good questions. Why wait for an interview when you can glean some of that right up front, the facts will remain the same, you need the real scoop on these folks.

    I think the job application process in general is broken, for both sides of the parties. I think the employers are quite frustrated to hire duds or say it more politely, “the wrong fit” for the company.

    I know employees are frustrated to keep spending hours filling out applications and chucking them into a black hole and in many cases, to never hear from those companies, beyond an automatic email response.

    I have faith that the right fit will come along. That I will be noticed for all that I have to sincerely offer. I wish all of us here the best

    Employers – like Basecamp, I hope you find the right candidate for your posted positions.

    Employees – my fellow black hole surfers – I hope we find our new long-term job home soon, or now…now would be good too!!

    David, thank you for the article, I found it inciteful, and nice to hear some real frustrations validated. I also enjoyed reading everyone’s comments – unless they wanted the same job as me and then just for a moment – I did not enjoy it as much (sorry fellow black hole surfers).

  11. Once you complete the selection of your Head of Marketing it would be great to read on your thoughts on the process and some metrics like:
    -which % was under qualified, which correct and which over qualified
    – % of applicants that did invest in a good cover letter.
    -Did you read all the cover letters that were fine crafted?
    -How many candidates made to second or later rounds?

    If you have two very good and similar candidates, what makes you prefer one or another?

    1. I am also curious to know if better candidates applied at the beginning/the middle/the end of the process.

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