"You become like their therapist," Chesky told Fortune.
Yet one person who studies meetings said making an employee feel heard can have "amazing" outcomes.
Meetings are the main way Airbnb's Brian Chesky gets work done. Yet he says the one-on-one format with a direct report is fundamentally flawed.
"Almost no great CEO in history has ever done them," the Airbnb chief said in a recent interview.
That's because when an employee "owns the agenda," they bring up subjects managers don't want to discuss β and "you become like their therapist," Chesky said. Topics can also arise that would benefit other people at the company to hear, but instead, they're sequestered in a one-on-one.
Of course, there are certain times when a one-on-one makes sense, Chesky told Fortune in the interview β such as when an employee is having a difficult time personally and needs to confide to a boss privately.
But generally, he said, they're just not productive on a regular basis.
Chesky isn't alone. Although he has many direct reports, Nvidia CEO Jensen Huang also prefers to skip one-on-one meetings.
"I don't really believe there's any information that I operate on that somehow only one or two people should hear about," Huang said at Stripe Sessions earlier this year.
Making employees feel heard can have 'amazing' outcomes
While some leaders are cracking down, one expert previously told Business Insider that, when conducted correctly, one-on-ones can boost employee engagement, productivity, and overall happiness.
"The outcomes associated with effective one-on-ones are amazing," said Steven G. Rogelberg, an organizational psychologist who's also a professor at the University of North Carolina at Charlotte and the author of "Glad We Met: The Art and Science of 1:1 Meetings."
Rogelberg previously told BI that one-on-ones are more successful when the worker leads the conversation. He said managers should dedicate roughly 25 minutes a week and focus on the personal needs of employees as well as the practical aspects of the job.
Many managers avoid that first component, Rogelberg said, because it takes more effort.
But at the same time, workers need to do their due diligence, he said β showing up prepared to talk more than half the time. Some fruitful topics include: challenges, how a manager can better support a worker, and what's going well and what could be improved.
'Nitpicking sessions'
Chesky isn't the only boss who's over the one-on-one. In May, Aditya Agarwal, a former Facebook director, wrote in a post on X that after more than a decade of conducting such meetings with those who report to him, he determined they did more harm than good.
"They condition people to do spot checks on happiness and constantly be critical about things that aren't ideal. In practice, 1:1s descend into nitpicking sessions," Agarwal wrote as part of a thread.
Agarwal added that bosses should give feedback every three to six months rather than weekly. That approach, he said, could drive managers to pick up on patterns and give "holistic" guidance rather than weekly spot checks.
Over the past two years, American businesses have been engaged in a rapid-fire restructuring of their corporate hierarchies. In the name of "flattening," they've been waging war on middle managers β trimming an entire tier of supervisory jobs that Mark Zuckerberg derided as nothing more than "managers managing managers, managing managers, managing managers, managing the people who are doing the work." Following Meta's lead, Citi reduced its 13 layers of management to eight. UPS axed 12,000 of its 85,000 managers. And in September, Amazon announced plans to increase its ratio of workers to supervisors by at least 15%. "I hate bureaucracy," CEO Andy Jassy declared, echoing the zeal for "efficiency" that Elon Musk, one of the pioneers of the current corporate flattening, is now seeking to unleash on the halls of government.
But here's the thing: It's not just that tens of thousands of middle managers have lost their jobs. It's that the jobs themselves have been eliminated β and they may not be coming back.
To test that theory, I asked Revelio Labs, a workforce analytics provider, to crunch the numbers for me, using its database of job postings aggregated from across the internet. It divided employees into two buckets of managers (senior leadership and middle management) and two buckets of lower-level employees (experienced associates and junior workers). Then it looked at how many job openings employers are posting today, compared with the hiring heyday of 2022.
What the data reveals is stark. Earlier this year, when white-collar hiring was at its lowest point, openings for junior roles β entry-level positions requiring little to no prior experience β were down by 14%. But hiring had plunged by 43% for middle managers and 57% for senior leaders. If you had any sort of management experience, your job prospects were bleak.
Since then, though, we've seen a significant rebound in job postings for almost everyone β except middle managers. In October, employers were still advertising 42% fewer middle-management positions than they did in April 2022. Which means that those who lost their jobs in the Great Flattening are now facing a whole new horror: There aren't any positions left for them to take.
The assault on middle managers dates back to the 1980s, when globalization gave rise to a new philosophy of management that prioritized cost cutting over everything else. Supervisors β earning big salaries for rubber-stamping the work of their subordinates β became an easy target. Trim the fat, the thinking went, and the efficiencies will follow. From 1986 to 1998, one study found, the number of managers reporting to division heads dropped by 25%. At the same time, the number of managers reporting directly to a CEO nearly doubled.
Executives got the flattening that they wanted. But it's unclear whether getting rid of middle managers actually made companies run more efficiently. As I wrote last year, one study found that businesses with fewer layers of management were able to deliver their products faster. But study after study found that when middle managers do their jobs right, they bolster performance more than either top executives or ground-level employees. Supervisors do real work. They motivate. They mentor. They communicate critical information to and from different parts of the company. They smooth out glitches and spot opportunities. They're the ones who keep the trains running.
But now is an especially bad time to be an experienced supervisor. According to an analysis by Live Data Technologies, another workforce analytics provider, middle managers made up 32% of layoffs last year, compared with 20% in 2019. And as the data from Revelio Labs shows, companies appear to have no intention of refilling those supervisory roles, even as they resume hiring for lower-level jobs. That has created a double whammy for middle managers: There's a sharp spike in job seekers, and they're competing for an increasingly small universe of open roles.
Over the past year I've heard from hundreds of managers mired in this double whammy. What's struck me is how eerily similar their stories are. They all come across as smart and articulate. They're all in their late 40s to 50s. When they got laid off from their supervisory jobs, they didn't expect their job search to be too difficult. After all, they'd spent decades honing their skills and climbing the corporate ladder, often at leading companies. Surely, all that experience had to count for something. But despite sending out hundreds of applications, they can't get anyone to return their calls. They're utterly baffled, and they all have the same question: What is going on here?
It's only after seeing the data that I finally understand what's going on: There just aren't enough supervisory jobs to go around.
It's the question I've been asking, too β combing through government data, talking to employers and economists, studying applicant-tracking systems. Because so many of the frustrated job seekers are older, I thought maybe we were seeing some new form of age discrimination: Call it the Curse of the Gen X Professional. But it's only after seeing the data from Revelio Labs that I finally understand what's going on: There just aren't enough supervisory jobs to go around anymore.
In response, many displaced managers have swallowed their pride and started applying to jobs lower on the corporate food chain. As Revelio Labs' data shows, nonmanagerial jobs are faring much better these days β and you'd think companies would be thrilled to get the experience and know-how of seasoned professionals on the cheap. But take the example of a former middle manager I'll call Rick, who is 54. After getting rejected for all the supervisory jobs he could find, he widened his search to include entry-level positions β only to be rejected for being overqualified.
At this point, all Rick wants is a chance to prove himself. "Forget the titles, forget all that other stuff," he told me. "I just need a job. My unemployment runs out in about 30 days. I'll come in and do a great job for you."
What all the out-of-work managers want to know is: When is the hiring freeze for supervisors going to thaw? That depends, in large part, on whether companies come to view the flattening as a success. Many CEOs insist they aren't getting rid of middle managers just to save money. They think having fewer layers of management will, as Zuckerberg put it, create a "stronger" company that can build "higher-quality products faster." That hints at a dark prospect for managers like Rick: The rung of the corporate ladder they spent their careers reaching could be gone for good.
There's a chance, of course, that the current craze for corporate flattening could ease over time. Companies are already discovering that having few middle managers is placing an enormous strain on their operations. The supervisors who survived the purge have been forced to take on much larger teams, and they're burned out to a crisp. Gen Zers, deprived of their mentors, are increasingly disengaged. Departments are more siloed than ever, with no one to do the tedious and thankless and essential work of coordinating across different teams. The best hope for managers like Rick is that CEOs are getting a real-time refresher in the value of managers.
"I'm not at that point in my life where I'm ready to take that step back," Rick told me. "I just want to work with good people and enjoy what I'm doing. I could go to Domino's and start delivering pizza. But I know I can do a lot more than that."
Aki Ito is a chief correspondent at Business Insider.
One of the fastest monopoly trials on record wound down Monday, as US District Court Judge Leonie Brinkema heard closing arguments on Google's alleged monopoly in a case over the company's ad tech.
Department of Justice lawyer Aaron Teitelbaum kicked things off by telling Brinkema that Google "rigged" ad auctions, allegedly controlling "multiple parts" of services used to place ads all over the Internet, unfairly advantaging itself in three markets, The New York Times reported.
"Google is once, twice, three times a monopolist," Teitelbaum said, while reinforcing that "these are the markets that make the free and open Internet possible."
Elle took a job in the tech industry about seven years ago, right when product management was "getting hot," she says. While the companies she's since worked for have had vastly different expectations of her, one thing has been consistent: clashes with other teams. Product managers serve as a bridge between engineers, salespeople, customer-service agents, and workers in other departments, and getting them to work together to build products that people actually need can be fractious.
"If you're an engineer and you have an idea, and then you have this outside figure come in and say, 'Why are you doing it this way?' β some can see that as great collaboration," says Elle, who asked that I use only her first name. "Other people are like, 'Whoa, you're slowing me down.'"
The product manager has become a powerful, highly paid, and polarizing figure. At some tech companies their colleagues refer to them, both affectionately and disparagingly, as "mini-CEOs" of the products they manage. Google's Sundar Pichai, Microsoft's Satya Nadella, and YouTube's Neal Mohan climbed their way up from product manager to CEO, and they deploy legions of PMs to help run their companies.
Coworkers don't always have fuzzy feelings about product managers. X abounds with snarky memes about their purposelessness, their illiteracy of Python and C++, their penchant for saying "no updates from me" in update meetings. On forums and subreddits, their more-technical colleagues belittle their work as fluff. "Is product manager the most useless role in tech?" an engineer posted on Blind. Another accused product managers of "stealing a living": "As an engineer, I feel I can easily do their job in addition to mine with not much extra effort," they wrote. One person on Reddit argued that product managers "just attend meetings and get paid more than the actual people doing the work."In a LinkedIn post titled "Product is too important. So we got rid of product managers," the founder of a digital banking startup wrote, "Any function that needs a decade to explain what it actually is or isn't doing is at very high risk of somehow being lost."
Several companies, from Airbnb to Snap, are now reconsidering the utility of product managers entirely, while others claim that the product manager's reign will only expand in the age of AI. How did a role that barely existed before the 2000s become one of the most influential and controversial presencesΒ in tech?
The seed of product management dates back to at least the 1930s, when Procter & Gamble created a position called the "brand man" whose job it was to understand customer problems. Inspired by this, Hewlett-Packard pioneered the tech product manager role in the 1960s. Microsoft began hiring what it called "program managers" in the 1980s. In the 2000s, as companies like Apple, Google, and Amazon expanded to create ever more products, product managers proliferated. Hardware and software also became more complicated, and the engineers and developers building it had less time to figure out what was actually useful β companies realized they needed someone dedicated to translating customer needs.
Product became a path into tech for people with backgrounds in consulting or MBAs. A "golden era" of product management emerged in the run of zero interest rates in the 2010s. Companies gobbled up talent, sometimes hiring beyond their needs just to keep smart workers from going to competitors. Big Tech companies became bloated, paying middle managers high salaries to optimize products and development. Carnegie Mellon University began offering what it calls a first-of-its-kind master's degree in product management in 2018. The next year, U.S. News and World Report named product manager a top-five job for MBA grads.
"The shift in power moved from engineering to product managers," says Hubert Palan, the CEO of Productboard, a company that provides software for product managers. That's part of the friction: Those on the tech side often think the product manager doesn't understand how things work, but the product manager may think the engineers are building tools that people don't actually want or need, even if they're feats in coding.
"The product manager is at the center of everything," says Avi Siegel, a former product manager who's working on his own startup, Momentum. "If sales wants one thing and marketing wants one thing and customer success wants one thing, they disagree, and you can only choose one of the groups to side with β you're only going to keep one of those people happy."
"Product management is mostly necessary, but it can be done very badly," says Aaron, a software engineer who asked me to use only his first name. He says he's worked with both excellent and terrible product managers. At best, they bear the burden of understanding the tech a market needs. At worst, they don't acknowledge how technically difficult a solution they demand might be, which leads to ire, fatigue, and failure. "We would be asked for the moon with no collaboration," Aaron says.
Whether their coworkers are happy about it or not, product managers are gaining recognition. A 2007 study found that as the product-management role became more formalized at companies, projects were finished closer to deadlines and with more predictability. A 2020 report from McKinsey said that "creating a comprehensive product-management function" was one of the four most important things a company could do to grow its software business faster. According to ZipRecruiter, the average product manager in the US makes about $160,000. Software engineers, meanwhile, average about $147,000, and tech marketing specialists average about $87,000.
Product managers described the role to me as more intuitive and right-brained than left-brained (though there are plenty of technical PMs, many of them former engineers). The career site Zippia says the proportion of women working in product management rose to nearly 35% in 2021 from about 19% in 2010. That's compared to just 22% of all tech workers. Some women in product management I spoke to say part of the suspicion of their role's utility could be rooted in sexism. In 2022, two women who worked as product managers posted a TikTok explaining what they did for work, while they worked from a pool. The video drew hundreds of harsh comments. "Dealing with most product managers is a headache and a half and we usually hate talking to you," one person responded.
"Every woman that I've met with, if they're interested in a company, their first question is: Am I technical enough?" Elle says. "Every guy I've met, that question doesn't cross their mind." It makes her wonder if it's easier for men in product management to push back and say no to some ideas without looking like naysayers.
Empathy came up in every conversation I had for this story. Like a deft diplomat, a good product manager can empathize with the needs and concerns of every stakeholder, Palan says. Meg Watson, a product manager who has worked for Spotify and Stitch Fix, says product managers who try to rule with an iron fist "quickly learn that doesn't work." She describes working as a product manager as emotional and intense and says many of them experience the tension of their role daily. When she asks people looking for advice on getting into product management why they want to, they say they want power. "You will have power," Watson says. "You will also have accountability and pressure and stress."
And now some companies are ditching them. The Airbnb cofounder Brian Chesky said last year that the company had combined the product-management function with product marketing. The rising call for executives to go "founder mode" β a concept touted by Chesky and coined by the Y Combinator founding partner Paul Graham β has some questioning whether they should be delegating product decisions to product managers. A spokesperson for Snap told The Information last fall that it laid off 20 product managers to help speed up the company's decision-making. Smaller firms ponder the utility of bringing on product managers at all.
But others say the scope of product managers, though it may draw engineers' ire, is more likely to expand across the industry. "The future really does belong to product managers," says Frank Fusco, a product manager turned CEO of a software company called Silicon Society. As artificial intelligence gets more adept at coding, he says, some engineering tasks could become redundant β and that could be a boon for product managers. (Pichai, a former product manager, said last month that more than a quarter of Google's new code was created by AI.) Fusco says the AI boom is a classic product-manager problem: What do customers actually want the tech to do? As investors and executives are hungry for AI and many consumers are skeptical, Fusco predicts a rising demand for product managers to help bridge that gap.
"The revenge of the PMs is coming," he says. "I would expect to see PMs becoming more prestigious and empowered."
Amanda Hoover is a senior correspondent at Business Insider covering the tech industry. She writes about the biggest tech companies and trends.
