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The risks of “yes” and leadership

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


The rules of improv comedy are simple: say “Yes, and”. The performers are asked to accept each new idea presented on stage – “You’re wearing a fedora!” or, “We’re in New Jersey!” — and embrace a sense of utter uncertainty about where the act might go.

During the tumult of the pandemic, when standard operating rules were scrambled, some business leaders seemed to embrace this philosophy as well.

Elon Musk, for example, the chief executive of Twitter, laid down the company’s rules as they went, sometimes in an apparent attempt to laugh it off. He decided whether to reinstate former President Donald J. Trump on the Twitter polling platform. He then shared a obscene meme on this subject. He walked into the office on the first day with a sink (“let it sink in”). His tenure as leader has at times seemed to skew towards chaos disguised as comedy.

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

Sam Bankman-Fried, who has been accused of improperly using billions of dollars in client funds to support his business company, also displayed a cavalier attitude towards his own recent decision-making: “I improvise “, Mr. Bankman said. -Fried told the New York Times, referring to his cryptic tweets. “I think it’s time.”

Even for executives unlike Mr. Bankman-Fried or Mr. Musk – that is, those who do not face potential legal fallout from their actions or who have not laid off large parts of their staff – the past two years have demanded an unusual level of flux tolerance.

Leaders faced jagged markets, runaway inflation and bumpy supply chains. They rolled out back-to-office plans, froze them for the Delta and Omicron variants, then attempted a relaunch. The five-year plans were abandoned; even the five-month plans seemed tenuous. The bosses accepted that they didn’t know all the answers and communicated this to their teams. Some have done it very well.

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

“It’s late night fraternity leadership,” said Margaret O’Mara, a University of Washington history professor and author of “The Code.” “It is now having an outsized effect on the broader realms of business, politics and culture.”

Technology has long prided itself on straying from buttoned-up corporate standards. The industry took shape in the 1980s as people became increasingly skeptical of traditional workplaces and ‘big fat companies’, as Ms O’Mara put it. Some of the most disruptive companies in the tech industry – Meta and Uber, for example – have been run by people who are known for being open to fast, uncontrolled and haphazard decision-making. Some of them settled into positions of authority at a young age, so their teenage, irreverent ways were quickly cemented, even celebrated.

But for workers, the stakes of these messy processes are high — like haphazard layoffs, as they were at Twitter. “A lot of what you see is incompetence,” said Johnathan Nightingale, co-founder of management training company Raw Signal Group. “It’s an internal chaos caused by a lack of attention to how the remaining employees experience their work.”

Yet, as tough times have given way to changing leadership styles, many other business leaders have modeled impromptu decision-making that feels much more functional. They have found the balance between flexibility and empathy, decisiveness and humour.

About 90% of human resources directors believe that successful leaders should focus on the human aspects of leadership, according to a survey by research firm Gartner. Almost a third of workers feel they have bosses who do this. Business leaders have spent the past few years making tough choices for their teams, and many have done so in a way that makes employees feel comfortable, even if managers remain honest about all the issues. unknowns they face.

Sali Christeson, for example, who runs workwear retailer Argent, has been through wild economic swings since the onset of Covid. In the spring of 2020, when she was eight and a half months pregnant, Ms Christeson furloughed nine of her 14 employees. She didn’t want to chase after a new line of products, like sweatpants. She hoped that at some point women would want to buy pantsuits again. Sure enough, this fall Silver sales peaked, especially in what the industry calls “dopaminergic dressing,” or bright colors, and Ms. Christeson expanded her team to 15 employees. She expects to be 20 in January.

Mrs. Christeson, at the time, felt like she was improvising. She had to make announcements at breakneck speed, just as she was about to start her maternity leave. She acknowledged that there were impending economic shifts — whether in back-to-office patterns or consumer spending — that she couldn’t foresee. She was candid with her team about these knowledge gaps.

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

Some business leaders have found that tense communication becomes easier over time. Rachel Drori, the head of 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 hold meetings with her bare hands after one of her company’s products – a lentil crumble – was recalled because it was linked to illnesses in some customers.

The discussion seemed a little easier because she had already spent two years in crisis resolution mode: “That muscle has gotten so much stronger,” she said.

An unpredictable business environment has pushed CEOs to deepen their management thinking, abandoning outdated approaches. It also highlighted the differences between leaders who lose the trust of their people and those who are able to deepen it. Mr. Nightingale, for example, has spent much of the pandemic helping leaders give their employees a sense of stability even when their industry or community has been rocked. It means acknowledging a broad sense of uncertainty, but not making it worse.

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

At Airbnb, executives were watching many other companies in 2021 make bold announcements about returning to the office. Airbnb decided to wait until last spring to roll out its plan, which allowed its employees to permanently travel remotely and work anywhere in the country. The company didn’t want to have to back down. Dave Stephenson, the company’s chief financial officer, said he recognized the long period of uncertainty was uncomfortable for some employees. He tried to mitigate this by communicating openly about how they approached the choice.

“Transparency is important, but clarity is perhaps even more important,” Stephenson said. “Helping people understand where we are with decisions along the way.”

And management in times of flux should not be humorless. Sara Mauskopf, who runs the Winnie childcare market, has seen demand for her services soar during the pandemic as the Covid crisis has created a care crisis. His work is serious. But lightness at work is also important to her. She laughs with her staff at times when their Zoom calls are interrupted by pets or thuggish parents. She lets them laugh at her.

She often thinks back to one of her own role models, former Twitter executive Dick Costolo. Mr. Costolo was the managing director when Ms. Mauskopf worked at the company, and she remembers him treating the weekly show of hands as a “stand-up comic”. But his jokes were never at anyone else’s expense.

After all, for a business leader facing uproar, even humor is an important issue: “Your version of failure is very different from the average person’s,” said Aparna Nancherla, a comedienne who played a human resources rep on the Comedy Central show “Corporate.” .” “There is more capacity to create chaos than normal people could afford.”



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