September 13, 2026

Presented By

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Louis Quail

Editor’s note

Good morning. We are writing this note to express our strong interest in welcoming you to Hiring Brew. Our background has equipped us to provide you with insights into how AI has swarmed both hiring and applying, the most bizarre questions that tech companies are asking interviewees these days, what “work trials” are and how job seekers are navigating them, and more. Looking forward to connecting!

job applications

AI is upending the hiring process

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Need a new job? Just use AI to polish up your résumé, submit an application to an AI-powered tracking system, interview with an AI agent, and then pass an AI background check.

Apply and demand

Many career advisors and universities are encouraging job seekers to use AI to craft their résumés and cover letters. But then recruiters have to figure out whether the candidate is a good communicator or just good at using AI. And while 60% of hiring managers say they can identify AI-generated applications, only about 25% actually can, according to a Software Finder survey.

AI also makes it easier to apply for jobs, turning recruiters’ offices into a ball pit of applications. According to hiring software platform Greenhouse:

In Q1 2022, the average job opening drew 89 applications.
Three years later, each opening attracted 243 hopefuls.

To keep up, 90% of US employers use AI screening, according to a Stanford University study. While those tools help weed out unqualified candidates, they also turn away talented prospects.

A hire calling: If you’re lucky enough to make it through the application gauntlet, it’s time to interview. But don’t bother practicing a firm handshake just yet. Nearly two-thirds of US job seekers say they’ve been interviewed by an AI bot, per Greenhouse.

Passing inspection: If you get past the interview process, there’s still one more AI hurdle to clear—an exhaustive digital background check that pulls your information from dozens of different places. So, if you’ve ever been in trouble with the law, posted something questionable on social media, or experimented with a goatee in college, there’s a good chance AI will find out and let your employer know.—BC

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wait, what?

What’s being asked at tech company job interviews?

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If you think first date questions are awkward, you might not want to be interviewed by a tech company. One of the latest examples: Anthropic reportedly asked candidates what they would do if the company abandoned AI and the stock went to $0.

But weird questions from tech managers are nothing new. Here are a few that have reportedly been asked, along with our suggested answers:

If a Nerf football hit you in the back of the head, what would you do? (Depending on the net worth of the person who threw it, sue.)
How many piano tuners are there in Chicago? (Zero. Chicago isn’t real.)
What would you do if you were the sole survivor of a plane crash? (Learn to fish, get really tan, and befriend a volleyball.)
What do you bring to the table that is world-class? (My ability to take a long lunch.)
How many golf balls does it take to fill a school bus? (Give me a driver, put me in a tee box next to a middle school, and let’s find out.)
If you were a Muppet, which would you be? (The only correct answer is Gonzo.)

Exit interview: While these questions seem like something a drunk guy at a bar or a precocious child would ask, these companies are looking for a candidate to offer a thoughtful and analytical response to show they can solve complicated problems.—DL

this is absolutely a test

Would you fake-work for a chance to get a job?

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Prepare your “working hard or hardly working?” quippy response: Companies want you to role-play as an employee before they finalize your offer letter.

Work trials aren’t brand new, especially in more technical fields, but companies are increasingly leaning on them to find qualified candidates in a job market flooded with AI-optimized résumés and cover letters:

It could be an unpaid mock task you complete off-site that mirrors what you’d do on the job.
On the other end of the spectrum, the work trial might be a week in the office with the team you could potentially join. If the work you complete on trial benefits the company, the candidate generally has to be paid for it.
About two-thirds of companies use some form of skill-based hiring for entry-level roles, according to a 2025 survey conducted by the National Association of Colleges and Employers.

In theory, a trial is great for checking a candidate’s skills and collaboration style while weeding out folks who are just really good at interviewing. But they can be a barrier to employed workers who can’t afford to take a full week off work for a long test that might not end in a job offer. And they can quickly turn exploitative when they’re unpaid.

Applying for a job feels like screaming into the void. Companies have spent the last few years downsizing after pandemic-era overhiring. With AI supercharging the hiring process from both sides, an in-person element could make finding a job more human…if a candidate can make it past the bots to get to that round.—MM

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glossary

A guide to the work culture buzzwords of LinkedIn

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It seems we can’t go a single quarter without new hiring jargon emerging that makes you ask “What does this mean?” and “Why do we need a whole phrase for this?” We don’t have an answer to the second question, but we are here to answer the first one:

Job-hugging: Also known as sticking to your current role. It’s less of a trend and more of a reaction to current economic uncertainty and the job market’s cooldown following the “great resignation” era of 2021 and 2022. Cue Jordan Belfort’s “I’m not leaving” speech.

Lily-padding: This is kind of like job-hopping for people who can’t stop thinking about Sylvia Plath’s fig tree. Lily padders leap from role to role—sometimes across industries—to gather a broad range of skills. The goal is to use those experiences to land a more senior job and settle into it for the long term…but the practice may also set off alarm bells for some prospective employers.

Career catfishing: It’s more than just a fun new way to say “I lied on my résumé.” Career catfishing applies to applicants who may exaggerate their qualifications or accept a job and never show up. It also applies to employers who are dishonest about a job’s responsibilities, benefits, or company culture when hiring.

Doomjobbing: You’ve heard of doomscrolling, now get ready for dopamine hits from absent-mindedly submitting job applications. Doomjobbers might throw their hat in the ring for hundreds of roles that don’t actually align with their goals, whether out of necessity or the compulsion to use couch time for something productive. But zinging off lots of Easy Apply submissions—which is often less effective than working hard on a few applications—may backfire on a job seeker by dinging their confidence.—ML

interview

Our hiring czar thinks cold LinkedIn DMing works

Job hunting can feel like a shamanic practice of summoning an offer letter. To demystify the process, we spoke with Morning Brew Inc.’s VP of Talent Acquisition, Lily Mittman, about what goes down on the receiving end of résumés, cover letters, and cold LinkedIn DMs.

We refrained from asking why our annoying coworker who microwaves tuna was hired, but we did learn a few tips that could help you land a job.

This interview has been condensed and edited for clarity.

Sam Klebanov: What should someone do to stand out in an interview?

Lily Mittman: Make sure you know the company you’re interviewing with, and that you’ve done your research: things like the company’s recent big wins, knowing some of the people on the team, knowing some names you can reference. Coming prepared with some good questions at the end is another way to show you did your homework.

Sam: Do you feel like there’s an advantage to word-of-mouth hiring?

Lily: Eight out of 10 times, we meet with somebody who’s an internal referral. If an employee we know can vouch that someone is great and qualified, we assign a lot of value to that referral. Also, for a job seeker who may not have a direct connection to the company, finding a connection to a mid-level employee is a good way to be seen.

Somebody who’s mid-level probably isn’t getting as many messages on LinkedIn as somebody who’s super super visible or super super senior, so they may be more likely to take the time to connect. So, find a mid-level connection and reach out, because if there’s a referral bonus internally, there’s incentive on both sides to make that connection.

Read the rest of the interview here.

mailbag

Recently, we asked you for nonobvious predictors of job performance that can be gleaned during hiring, and you exceeded all expectations. Here are a few we would’ve never thought of:

“Early in my career, I hired a candidate who was very introverted, but came alive when I asked about his thesis on Nietzsche. I figured if he could get excited about that, he could sell some of the most boring technology there is: backup software. Reader, not only was he a great salesperson, but also I married him.”—Sheryl from Boston
“I am a recruiter, and anytime I interview other senior recruiters, I always ask them what their friends do for a living. If you are a good recruiter, you can’t help but know every detail of your friends’ jobs, including how much they get paid.”—Brad
“I always start with the standard opening, ‘Tell me a little about yourself.’ If the answer lasts more than two minutes, it’s a hard no. Communicating in a clear and concise manner is a must in business, as is listening. I didn’t say ‘tell me your life story.’”—Steve from Springboro, OH
“I own a house painting business and I like to hire snowboarders/skateboarders. They tend to not have fear of ladder work.”—Frank from Lake Tahoe, CA
“When interviewing for an open position in my hospital, I usually give the interviewee an impossible clinical situation, hoping that they come to the conclusion that they need to ask for help. If they think they can do it all themselves, that’s a major red flag, and a potentially dangerous team member.”—Katie from Portland, OR

brew's best

ICYMI, use your Sunday morning to get caught up on some of our most-clicked recent recs:

How to clean your water bottle properly.
The decorating rules interior designers say you should never break.
A fall foliage prediction map so you can plan the perfect autumnal getaway.
What experts say to do if one of your berries goes moldy.
A fall doormat that nods to the season but isn’t too in-your-face.**

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Written by Brendan Cosgrove, Dave Lozo, Matty Merritt, Molly Liebergall, Abigail Rubenstein, and Holly Van Leuven

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