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Job interviewing and the medieval dungeon rack. The latter might be less painful. 🧌. They have become more difficult. Here are some reasons why and pro-active steps to make it more productive and successful.

13 Jan 2023 12:51 PM | William Strachan

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A person at a job interview.It should not take endless interviews to get a job.

Emily Stewart covers business and economics for Vox and writes the newsletter The Big Squeeze, examining the ways ordinary people are being squeezed under capitalism. Before joining Vox, she worked for TheStreet.

In late 2022, Jessica found herself in a predicament that will sound familiar to many job seekers: slogging through an extended interview process with seemingly no end in sight. 

She was up for a job as a fundraiser at a major social services organization in New York. Across the span of two months, she took part in six separate interviews with nine people total, multiple of whom she met more than once. She’d pulled one of her first all-nighters in years putting together a dummy presentation on a hypothetical corporate partnership for interview No. 4, which entailed what she describes as a 15-minute “monologue” from her on the matter followed by a 45-minute Q&A with a panel. It wasn’t until the final interview that she got a real one-on-one sit-down with the person who would be her boss.

“Every time I thought, ‘Okay, this is the final hump,’ there was another thing,” said Jessica, which is a pseudonym. Vox granted her anonymity in order to protect her privacy and keep her out of hot water with her current employer. “It just gets really mentally exhausting, and it’s hard to manage your work schedule because obviously you don’t want your employer to know you’re interviewing.” 



Job-seeking can be a real exercise in immersive futility. It often feels like you’re tossing your resume into the abyss and praying to the recruitment gods for a response. If and when you get that response, the landscape doesn’t always get easier. Companies are seemingly coming up with new, higher, and harder hoops to jump through at every turn. That translates to endless rounds of interviews, various arbitrary tests, and complex exercises and presentations that entail hours of work and prep. There can be good reasons for firms to do this — they really want to make sure they get the right person, and they’re trying to reduce biases — but it’s hard not to feel like it can just be too much.

“There’s no reason why 10 years ago we were able to hire people on two interviews and now it’s taking 20 rounds of interviews,” said Maddie Machado, a career strategist who has previously worked as a recruiter at companies such as LinkedIn, Meta, and Microsoft. “It’s kind of like dating. When you go on a first date, you need a second date. You don’t need 20 dates to know if you like somebody.”

COMPANIES ARE SEEMINGLY COMING UP WITH NEW, HIGHER, AND HARDER HOOPS TO JUMP THROUGH AT EVERY TURN

Jessica describes her recent marathon interview process as basically having a “second job.” As for the actual job in question, she didn’t end up getting it. A week after her last interview, Jessica followed up with the recruiter and learned the organization was moving forward with another candidate. “They probably wanted to go with the other person all along but wanted me as a backup,” she said. 

If you do not have a terrible interview story, sincerely, congrats

If you’ve ever looked for a job, chances are you’ve had some sort of a “what in the world is going on” moment. For Brad, a consultant in Pennsylvania who asked to withhold his last name, that moment came when he went through a series of interviews for a project management position in 2016. All of them went well — until he reached the CEO, who spent a significant portion of their nearly hour-long conversation dwelling on Brad’s somewhat low high school GPA, which the company had requested along with his college GPA and SAT scores. “I had to justify why my high school grade point average wasn’t top of the class,” he said. “I was offended.”

He’d graduated from high school some 30 years prior and had 25 years of work experience. When the company’s recruiter later called him to suggest he spend more time talking to the CEO, he said he wasn’t interested. “I had the luxury of not needing the job,” he said. “You’ve got to like who you work for.”

Reporting for this story, I heard anecdotes about hiring processes that ranged from irksome to hellish. 

One recent graduate described having to take a series of intelligence tests, go through two interviews, and provide five references — all of whom were asked to complete a 15-minute questionnaire — for an entry-level position at a nonprofit he was told he didn’t get two months later. One woman’s job offer was contingent on her getting a reference from her current manager, who wasn’t aware she was on the hunt for a job.

“MY INTERVIEWING EXPERIENCES HAVE BEEN WORSE THAN DATING, WITH THE GHOSTING AND NON-RESPONSES”

Another man was told to start looking for apartments across the country after being flown out for a final interview, only to follow up a couple of weeks later and learn that the recruiter simply forget to tell him he hadn’t gotten the job. “My interviewing experiences have been worse than dating, with the ghosting and non-responses,” he said. 

Among friends and colleagues, swapping interview horror stories can turn into a sort of sport. One of my former coworkers was asked to build out an entire content strategy for a popular financial newsletter and work with the team in the office. She was unemployed and scared, so she felt like she had no choice but to sign a waiver agreeing for her work to be used for free — work that was apparently good enough to be sent out to their readers but not to land her a position with the company. Looking at the company’s Glassdoor reviews, it’s obvious she’s not the only one who’s been subject to this sort of treatment.

“So many employers get away with this,” Machado said. “They get away with making people go through all these hoops because … candidates have absolutely no protection.”

The difference between okay and over-the-top isn’t always so obvious

What counts as a fair ask from a potential employer isn’t always clear-cut. It can depend on the industry, the job level, and the purpose.

“There’s a fine line between appropriate and inappropriate,” said Sondra Levitt, a leadership and career coach with Korn Ferry, an organizational consulting firm. For example, it might make perfect sense for a company to ask a candidate, especially at the executive level, to do some sort of presentation about their vision and what they want to accomplish. Where it gets hairy is when the company asks a candidate to create, produce, and submit a full-blown marketing campaign, which happened to one of Levitt’s clients recently. “The candidate felt like they were just trying to get free information and free work through the interview process,” Levitt said. 

There’s no denying that over the years, in many instances, the hiring process has gotten harder and more convoluted. A 2022 survey from hiring software company Greenhouse found that 60 percent of job seekers were “unimpressed by time-consuming recruitment processes.” There’s no concrete explanation as to why many employers have been so insistent on making the hiring process so hard — it’s likely an amalgamation of factors.

Companies are afraid to make the wrong decision. Hiring is expensive and onboarding is time-consuming, so they really want to get it right. The pandemic and current economic conditions may be exacerbating employers’ anxiety even more. Levitt said she thinks many firms feel like they “jumped too fast” to make hires amid the great resignation or great reshuffle, as for much of 2021 and 2022 workers hopped jobs in droves. The pendulum is swinging the other way now, with managers being extra careful to do their due diligence, especially as the economy looks rocky

Becca Carnahan, the founder of Next Chapter Careers, said that companies may see multiple interviews and tests as a way to make the hiring process fairer. “It can reduce bias in the hiring process when you’re actually looking at a candidate’s abilities rather than their past accomplishments,” she said. She added that technology has likely also played a role in making the hiring process more complex. “These Zoom interviews are a lot easier than bringing candidates into the office,” she said. 

Jessica, the nonprofit fundraiser, speculated that in her case, tech and remote work made it possible for her potential employer to drag things out longer. Before the pandemic, she would have probably had to go to the office one day for a string of interviews, the firm recognizing she couldn’t just disappear at random from her current job for weeks on end. But with her simply clicking a Zoom link, the company was able to sprinkle interviews across multiple weeks. 

Machado believes that the increasingly long maze of recruitment and interviewing is driven, in part, by pride and by companies competing against each other to be considered the most elite places to work, especially in the tech world. “You want to be the most challenging interview. If you can get past the Facebook interview, you can get past anything,” she said. The caveat is that the best interviewers are not always the best people for the job, and a difficult interview process does not guarantee the candidate won’t quit. “There’s too much emphasis on screening people out and not on screening people in.”

Perhaps the simplest answer to why companies make it so hard is that they can.

In 2005, it took two interviews for Stacey Aldstadt, an environmental lawyer, to get her job as general manager of the city of San Bernardino’s municipal water department, from which she retired in 2017. While there, she oversaw 300 employees and a $120 million budget. In late 2020, she decided to apply for a job at a cannabis company looking to expand to California. She was subjected to a seven-interview, eight-week hiring process that culminated in an impersonal rejection email without explanation. Aldstadt has hired people in the past, and this seemed incredibly excessive. “I would never do that to someone,” she said. “Not in a million years.”

Candidates can push back, but leverage is limited

If and when candidates feel like the employer is overdoing it in an interview process, the options are a little limited. To a certain extent, you kind of just have to go with it or walk away. But there are ways to navigate.

It’s helpful to ask questions to ascertain expectations around interview assignments — figure out why they’re relevant and how they’ll be evaluated, and get assurances that the work remains proprietary. You can also try to decipher if there are alternatives, such as providing samples of previous work, or asking for compensation, though the answer might be no. At the outset of the hiring process, it’s also a good idea to ask exactly what it’s going to entail — how many interviews, with whom, on what timeline — and hold the company or recruiters to it. 

“If a company is not communicating effectively with a candidate, if they are super opaque about the process and the timing, that’s where it gets really, really icky, and it can leave a candidate just feeling so confused,” Carnahan said. 

“YOU’RE DEFINITELY INTERVIEWING THE COMPANY AS MUCH AS YOU’RE BEING INTERVIEWED”

Candidates should also set some boundaries, which are different for everyone. Machado generally recommends the job seekers she works with do no more than four rounds of interviews. And if they’re asked to do a presentation or take-home assignment, it’s time to evaluate whether it’s a place they really want to work. Sometimes, candidates worry the potential employer will use their work. It might be more often the case that they don’t look at all. “They’re making people do these assignments, and then no one checks it,” Machado said. 

It’s important to remember that if a company’s hiring process feels off, working there might feel off, too. An employer having to reschedule multiple interviews because the interviewers are swamped at work might be a sign that things aren’t great, internally. “You’re definitely interviewing the company as much as you’re being interviewed, so stay attuned to what you are hearing and seeing,” Levitt said. “What’s your gut telling you about this company? About this job? About the organization?”

Companies should take note that being a complete pain to deal with in recruiting is not great for their reputations, either. They can stall so much or put candidates through such a rigamarole by the time they put out an offer, the candidate’s just over it. More broadly, while job seekers may not have a lot of options to fight back, they can talk to others about their experiences, and they definitely do.

Jessica says knowing what she knows now, she still probably would have applied for the fundraising job. Still, she wishes the organization hadn’t checked her references as a last and apparently unnecessary step. “It was a little weird for someone to be like, ‘Oh what happened to this? Did you get that offer letter?’ and you’re like, ‘Oh, actually, I didn’t get the job.’”


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