The Risks of ‘Yes, and’ Leadership

This article is part of our special section on the DealBook Summit that included business and policy leaders from around the world.


The rules of improv comedy are straightforward: Say “Yes, and.” Performers are instructed to accept every new idea introduced onstage — “You’re wearing a fedora!” or, “We’re in New Jersey!” — and embrace a sense of utter uncertainty about where the act might be headed.

During the tumult of the pandemic, when standard operating rules were scrambled, certain business leaders seemed to adopt this ethos, too.

Elon Musk, for example, Twitter’s chief executive, has been making up company rules as he goes along, sometimes in an apparent attempt for laughs. He decided whether to reinstate former president Donald J. Trump on the platform by Twitter poll. He then shared a lewd meme about it. He walked into the office on his first day carrying a sink (“let that sink in”). His leadership tenure has sometimes seemed to skew toward chaos dressed as comedy.

“It’s far more than transparency,” said Bob Faw, a leadership consultant. “It’s thinking out loud.”

Sam Bankman-Fried, who has been accused of improperly using billions of dollars of customer funds to prop up his trading firm, has also displayed a cavalier attitude toward his own recent decision-making process: “I’m improvising,” Mr. Bankman-Fried told The New York Times, referring to his cryptic tweets. “I think it’s time.”

Even for leaders unlike Mr. Bankman-Fried or Mr. Musk — that is to say, those who are not facing potential legal fallout from their actions, or haven’t laid off sweeping portions of their staff — the last two years have demanded an unusual level of tolerance for flux.

Executives confronted roller-coaster markets, soaring inflation and bumpy supply chains. They rolled out return-to-office plans, froze them for the Delta and Omicron variants, then attempted a relaunch. Five-year plans were scrapped; even five-month plans seemed tenuous. Bosses accepted that they didn’t know all the answers and communicated that to their teams. Some did this quite well.

But a number of tech executives, particularly Mr. Musk, have taken the notion of ultra-honesty and uncertainty to new extremes.

“It’s late-night frat house leadership,” said Margaret O’Mara, a history professor at the University of Washington and author of “The Code.” “It’s now having an inordinate effect on larger realms of business, politics and culture.”

Tech has long prided itself on its departure from buttoned-up corporate norms. The industry took shape in the 1980s as people were growing skeptical of traditional workplaces and “fat-cat big business,” as Ms. O’Mara put it. Some of the tech industry’s most disruptive companies — Meta and Uber, for example — have been headed by people who set themselves apart with an openness to fast-moving, unchecked, messy decision-making. Some of them settled into positions of authority at a young age, so their adolescent and irreverent habits were quickly cemented, even celebrated.

But for workers, the stakes of those messy processes are enormous — like layoffs carried out haphazardly, as they were at Twitter. “A lot of what you’re seeing is incompetence,” said Johnathan Nightingale, co-founder of the management training firm Raw Signal Group. “It’s internal chaos driven by a lack of care around how employees still on the job are experiencing their work.”

Yet as shaky times have given way to changing leadership styles, many other business leaders have modeled improvisational decision-making that looks much more functional. They’ve found the balance between flexibility and empathy, decisiveness and humor.

Roughly 90 percent of human resource directors believe that successful leaders have to focus on the human aspects of leadership, according to polling from the research firm Gartner. Nearly a third of workers feel they have bosses who do this. Business leaders have spent recent years forced to make abrupt choices for their teams, and many have done so in a way that keeps employees feeling comfortable, even as managers remain honest about all the unknowns they’re confronting.

Sali Christeson, for example, who runs the work-wear retailer Argent, has navigated wild economic swings since Covid’s onset. In spring 2020, while she was eight and a half months pregnant, Ms. Christeson furloughed nine of her 14 employees. She didn’t want to chase a new product line, like sweatpants. She was hopeful that at some point women would want to buy pantsuits again. Sure enough, this fall Argent’s sales have peaked, especially in what the industry calls “dopamine dressing,” or bright colors, and Ms. Christeson has grown her team to 15 employees. She’s expecting to be at 20 by January.

Ms. Christeson, at the time, felt like she was improvising. She had to make dizzyingly quick announcements, just as she was about to start maternity leave. She recognized that there were economic shifts looming — whether in return-to-office patterns or consumer spending — that she couldn’t predict. She was candid with her team about those gaps in her knowledge.

“I’m always the first to tell you when I have no idea what I’m doing,” said Ms. Christeson. “But the team has always and is always looking for me to make the decisions.”

Some business leaders found that fraught communication got easier over time. Rachel Drori, the head of the frozen food company Daily Harvest, had to explain to her team in 2021 why she was cutting the company’s marketing budget. Then, in June, she had to host all-hands meetings after one of her company’s products — a lentil crumble — was recalled because it was linked to illnesses among some customers.

The discussion felt somewhat easier because she’d already spent two years in crisis-solving mode: “That muscle has grown so much stronger,” she said.

An unpredictable business environment has pushed chief executives to deepen their thinking on management, scrapping outdated approaches. It has also made clear the differences between leaders who lose the trust of their staff and those who are able to deepen it. Mr. Nightingale, for example, has spent much of the pandemic helping executives give their employees a sense of stability even when their industry or community has been rocked. That means acknowledging a broad sense of uncertainty, but not heightening it.

“Even if the world outside is really chaotic, I can understand what my job is if I can trust my colleagues, if I know what we’re focused on,” Mr. Nightingale added.

At Airbnb, executives were watching plenty of other companies in 2021 making bold announcements on returning to the office. Airbnb decided to wait until last spring to roll out its plan, which allowed its employees to go permanently remote and work anywhere in the country. The company did not want to have to backtrack. Dave Stephenson, the company’s chief financial officer, said he recognized that the extended period of uncertainty was uncomfortable for some employees. He tried to mitigate that by communicating openly about how they were approaching the choice.

“Transparency is important but clarity is maybe even more important,” Mr. Stephenson said. “Helping people understand where we’re at with decisions along the way.”

And managing in periods of flux doesn’t have to be humorless. Sara Mauskopf, who runs the child care marketplace Winnie, saw demand for her services explode during the pandemic as the Covid crisis created a care crisis. Her work is serious. But levity in the workplace matters to her, too. She laughs with her staff about the moments that their Zoom calls are interrupted by pets or rogue relatives. She lets them poke fun at her.

She often thinks back to one of her own role models, Dick Costolo, a previous head of Twitter. Mr. Costolo was the chief executive when Ms. Mauskopf worked at the company, and she recalls him treating the weekly all-hands as “stand-up comedy.” But his jokes were never at anybody else’s expense.

After all, for a business leader facing tumult, even humor is high stakes: “Your version of failure is way different than for the average person,” said Aparna Nancherla, a comedian who played a human resources representative on the Comedy Central show “Corporate.” “There’s more capacity to create chaos that normal people could not afford to do.”



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