DON’T BE A JERK AT WORK. (BUT DON’T BE TOO NICE, EITHER.) - Kanebridge News
Share Button

DON’T BE A JERK AT WORK. (BUT DON’T BE TOO NICE, EITHER.)

How devolving into people-pleasing can hold back your career

By RACHEL FEINTZEIG
Tue, Aug 8, 2023 10:27amGrey Clock 4 min

How nice should you be at work?

We’ve supposedly moved on from the era of the militaristic chief executive who barks orders and threats. Most of us agree: We don’t like jerks. Be kind, we implore our kids.

Then we get to the office. We’ve got direct reports to rally, colleagues in other departments to convince and bosses who claim they want honest feedback. Speak with hesitation and you’re ignored. Handle your team with kid gloves and you’re a pushover, not a force to be reckoned with.

“I, personally, think you’re too nice a person to be in the job that you’re in.” That’s what Rep. Greg Murphy (R., N.C.) told Katherine Tai, the lead trade negotiator for the U.S., this spring during a hearing. His comments summed up feedback so many of us, especially women, have heard. We’re too bubbly or kind. We deploy too many apologies or exclamation marks. Yet when we do too little of all that, we’re overly aggressive.

“I want to be a nice person,” Sarah Kleinberg, the director of operations at a healthcare consulting firm, told me. She has realised, though, that being nice often makes others feel good, without actually moving a project forward or prompting a team member to improve.

“You have to have the level of confidence to be beyond people-pleasing,” she says.

‘Customer-service voice’

Many people, desperate not to offend, resort to what speaking coach Samara Bay calls “customer-service voice.” It’s that high-pitched, upspeak-y tone meant to inform the barista, I think you might be out of oat milk?

What are we saying when we use that tone? “I’m not powerful, don’t worry,” Bay says.

Making yourself non intimidating and as small as possible might work earlier in careers, she adds, making the people in charge feel secure. But as we ascend, or try to, the wavering voices can confuse others. Do it enough and people might question whether you’re leadership material, Bay says.

She recommends a vocal exercise for speaking more confidently. Pretend that you’re introducing yourself—“Hi, my name is Rachel”—while throwing a pretend ball against the wall. Match your vocal pitch to the ball’s trajectory. When you throw the ball down to the ground, you’ll hear your voice droop in energy along with the ball. Then throw the ball up, and notice the way your words sound as if you’re half taking them back. Last, throw the ball straight and allow your words to follow through, too.

“It’s the weirdest feeling to say something and mean it all the way to the end,” Bay says. “It feels brave.”

No hedging allowed

When pitching an idea, don’t undercut yourself with hedging language, says Bob Bordone, a negotiations coach. He cringes at questions like: “Would you be willing to consider letting me work remotely on Fridays?”

“It makes me just want to say no because it’s such a weak thing,” he says.

Instead, he says, start with a statement: “I wanted to talk to you about working out a new schedule.” Assure that any agreement you come to would be good for your manager and the company.

When someone tells you no, Bordone suggests trying: “How can we tackle this, even though we see it differently?” You sound strong and assertive, but not nasty, he says.

Good news for the nice guys among us: You don’t have to give up your personality to be taken seriously.

“I’m, 99.9% of the time, a jovial, happy-go-lucky guy,” says Colton Schweitzer, a user-experience designer and educator in Vancouver, Wash. When he doesn’t like the direction a project is going, he pushes back by asking questions and inserting the occasional joke.

“I’m smiling,” he says, “Even when I’m saying, ‘Are you sure about that?’”

Because he’s so pleasant, his serious moments carry weight. At one job, he cheerfully took on more work when colleagues asked—until his manager asked him to pick up the slack for an underperforming employee. He gave a resolute no. His manager dropped the issue, and seemed surprised and impressed by his response, he says.

“It’s like a currency,” he says of invoking a more stern style. “When I use it, it’s really valuable.”

Less yelling, more intensity

To be tough but not jerky, set clear expectations, says Harry Kraemer, a professor of leadership at Northwestern University’s Kellogg School of Management.

Before teaching, Kraemer rose to be chief executive of Baxter International, the healthcare company where he worked for 25 years. As a new manager, he would try to be everyone’s breezy friend, shrugging it off when his team turned in a project hours past deadline. The second time it happened, he devolved into yelling, only to realise he hadn’t made the stakes clear from the start.

“If I focus on being liked, the chance of being respected is very low,” he says.

He adopted a new leadership style of, “I’m not going to surprise you.” He says the yelling just made him look out of control, but following through with consequences worked. When his team missed sales targets, he gathered them for a two-hour debrief—no smiling, his voice intense.

“I don’t need a sorry,” he would tell them. “Hit the number. Do what you told me you were going to do.”

Dinah Davis, a Realtor in Highlands, N.C., still remembers advice an old friend gave her years ago on the golf course. The friend was a skilled neurosurgeon known for being direct, not touchy-feely.

“I have a great bedside manner,” she told Davis. “I just don’t have time for it.”

The advice was freeing for Davis, a former lawyer more comfortable with staunch negotiations than chirpy small talk.

“Do you want your pilot to be nice?” Davis asks. “Or do you want your pilot to get the plane on the ground?”



MOST POPULAR

BNW Developments has established a Sydney presence, joining Arada and Sobha Realty among the growing number of UAE developers pursuing Australian buyers and development opportunities.

The Australian leather house has opened an immersive four-day pop-up in Manhattan, unveiling its Bloom Collection and redefining what a product launch can look like.

Related Stories
Lifestyle
AI Agents Are a Threat to Travel Businesses. Airbnb Could Still Be a Winner.
By David Wainer 13/10/2026
Lifestyle
Amazon in Talks to Buy AI Startup Decart for Around $7 Billion
By Kate Clark and Lauren Thomas 12/10/2026
Lifestyle
Dolly Parton’s Onetime Hollywood Hills Home Lists for the First Time in a Generation Asking $7.95M
By 06/10/2026

AI-powered travel agents are challenging online booking platforms, but Airbnb’s exclusive listings and direct customer relationships could give it an edge. Its next challenge: turning repeat guests into loyal customers through stronger rewards and innovation.

By David Wainer
Tue, Oct 13, 2026 3 min

AI agents like Muse can already find you the cheapest hotel room in Paris. But they can’t locate a cheaper version of that Catskills cabin you’ve been eyeing, because it might only be available on Airbnb ABNB -1.43%decrease.

Investors should pay attention to that distinction. When Meta Platforms META 3.38%increase launched its Muse agent last month, travel stocks including Booking Holdings BKNG -1.19%decrease, Expedia and Airbnb all fell sharply.

Airbnb, though, has a real chance to emerge as a winner from the upheaval. The catch: Its stock already reflects above-industry growth. To justify its valuation, Airbnb will need to turn repeat customers into loyal ones.

Online travel companies make much of their money by simplifying search and collecting fees on bookings. AI agents threaten that model.

But not all travel marketplaces are equally exposed. Booking and Expedia largely sell hotel rooms that travelers can also book directly or through competing sites. If an agent can find the same room elsewhere, it has little reason to favor either Booking or Expedia.

Booking and Expedia also sell sponsored listings that steer travelers toward particular properties. Wells Fargo estimates those will account for about 8% of Expedia’s revenue and a much higher percentage of profit next year.

Airbnb has more ways to adapt. More than half its listings are available only on its platform, and more than 90% of its traffic comes directly to its app or website.

The customer relationship doesn’t end after booking, either. Bernstein analyst Richard Clarke notes that 90% of Airbnb guests go on to message their hosts about arrival times, keys or local taxes, giving Airbnb a connection to both sides of the transaction.

How the companies have responded to the possible agentic future is telling.

Expedia quickly signed on as a Muse partner. Airbnb hasn’t, and Chief Executive Brian Chesky says AI chatbots have so far been a boon, sending customers to Airbnb’s website.

Chatbots might work for buying paper towels, he quipped at a Skift conference last month, but people enjoy planning trips. He argued that browsing dozens of homes isn’t something a text-based chatbot is well suited for.

Still, the AI jitters arrived just as Airbnb was persuading investors it deserved its pricey multiple. For years after its 2020 initial public offering, the stock—which trades around 25 to 30 times forward earnings—went nowhere. Investors saw a mature operator trading at a growth premium.

This year, Airbnb growth seems to be accelerating. The stock jumped in August after the company raised its full-year revenue-growth guidance with its second-quarter results. Wells Fargo analyst Ken Gawrelski credits a run of product improvements under a revamped leadership team.

Among the changes: letting guests reserve now and pay later, adding hotels, and a redesigned home page and app. Investors were also betting on what comes next, including thousands more hotels, car rentals and, eventually, advertising.

The irony is that some of those growth drivers push Airbnb closer to the kind of business Booking and Expedia run—the kind of business AI agents could threaten. Even if AI agents capture a large share of travel planning and booking, Airbnb would capture the demand. But it and others would slowly lose control over how customers find and choose properties.

That would undermine the advertising opportunity investors are counting on. The bigger point for Airbnb and other marketplaces is that losing control of customer acquisition could mean surrendering some of their pricing power and margins.

To bulletproof itself, Airbnb might look to another e-commerce giant that has so far kept AI agents at arm’s length: Amazon.

Like Amazon, Airbnb has a loyal customer base and hard-to-match supply. But it has nothing like Prime membership to make customers think twice before taking their business elsewhere.

That is where loyalty comes in. Business travelers stick with Hilton or Marriott because enough nights earn them perks. Leisure travelers rarely accumulate stays with one chain. Airbnb has millions of listings and plenty of repeat customers, but no broad rewards program. It has begun experimenting with credits on hotel stays, but it should make loyalty a priority, not just a promotion.

Airbnb also plans to launch its own AI agent next year. But travelers using an agent might still want it to search Airbnb, Vrbo, Booking and hotel websites alike, rather than limit itself to one company’s inventory.

Eventually, Airbnb might have to strike deals with agent makers, using its unique homes as leverage to negotiate favorable terms, says Gawrelski. Such deals, along with rewards for loyal guests, could over the long term eat into the company’s roughly 13% take rate, he adds. But if they bring in enough additional bookings, the trade-off could be worthwhile.

History offers a reason not to panic. The shift from desktop to mobile unsettled investors in Alphabet and Amazon, but both emerged as major beneficiaries. Companies with valuable assets can come out of a platform shift stronger, if they adapt quickly enough.

Airbnb has homes the bots can’t easily replace. Now it needs to give guests a reason to insist on booking them there.