Don’t Be a Jerk at Work. (But Don’t Be Too Nice, Either.)
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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 1, 2023 8:34amGrey 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?”



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The Budget Wake-Up Call for Wealthy Australians

The Federal Budget may have softened some of its proposed tax reforms, but it has exposed a bigger issue: too many families are relying on wealth structures that no longer reflect the realities of modern life.

By Opinion, Anthony Hunt
Mon, Jun 22, 2026 3 min

For many Australians, the 2026 Federal Budget initially felt like a direct challenge to the way wealth is created, held and transferred between generations.

The headlines were immediate: changes to capital gains tax, reforms to discretionary trusts, restrictions on negative gearing and increased scrutiny of investment structures. Unsurprisingly, affluent families, business owners and investors began asking the same question:

Is the way we hold our wealth still fit for purpose?

In recent days, the government has announced several significant amendments following industry consultation and public feedback, including exempting testamentary trusts from the proposed 30 per cent minimum tax and expanding capital gains tax concessions for small businesses.

The backdown is welcome. But it also highlights something much bigger.

This Budget has accelerated a conversation that many Australian families have been postponing for years.

The conversation is not really about tax. It is about wealth stewardship.

For decades, Australians have built wealth through businesses, property, investments and careful long-term planning. Yet many families have not revisited the legal structures surrounding those assets in years, sometimes decades.

We often see clients who have spent years building significant wealth, only to discover their legal arrangements no longer reflect their current circumstances.

Their children are now adults. They may own multiple properties.

They may have sold a business, entered a second marriage, become grandparents or accumulated digital assets that did not exist when their original estate plans were prepared.

The trust that distributes income may need to be reconsidered. The bucket company may no longer be so attractive.

The Budget has simply exposed a reality that already existed: wealth structures cannot remain static while life continues to evolve.

Importantly, trusts themselves are not the issue.

Trusts are legitimate planning tools that provide flexibility, protection and continuity. When used appropriately, they allow families to adapt to changing circumstances over time.

And neither is tax the issue, really. Getting the fundamentals right is more important for long-term, sustainable wealth than a few favourable tax treatments around the edges.

Anthony Hunt

The real issue is complacency.

Too often, families create structures and assume the job is done. It isn’t.

Estate planning is no longer a document you sign once and file away in a drawer. It is an ongoing process that should evolve alongside your life.

We are also seeing a broader shift in how Australians define wealth itself. It is no longer just the family home and an investment portfolio.

Modern wealth includes businesses, digital assets, cryptocurrency, intellectual property, frequent flyer points and increasingly complex family arrangements.

At the same time, Australians are living longer than ever before, meaning wealth may need to support multiple generations simultaneously. This creates new responsibilities and new risks.

How do you help your children enter the property market without exposing family wealth to relationship breakdowns?

How do you structure wealth so that it remains a source of opportunity rather than future conflict?

These are the questions families should be asking now.

The recent debate surrounding testamentary trusts also serves as an important reminder that policy decisions can have unintended consequences for vulnerable Australians. It is encouraging that the government has listened to feedback and clarified its position.

But the lesson remains: the wealth landscape is changing.

Increasingly, governments, regulators and tax authorities are paying closer attention to how wealth is held and transferred. That means families cannot afford to adopt a “set-and-forget” approach to their structures.

The families who will be best placed for the future are not necessarily those with the greatest wealth.

They are the families with the greatest clarity. Clarity around ownership, succession and governance. And clarity around how wealth will transition from one generation to the next.

Ultimately, preserving wealth is not about avoiding change.

It is about preparing for it.

Because the greatest risk is not change itself.

It is losing the ability to respond to it.

Anthony Hunt is Co-Founder of Wealth Lawyers and former COO of Westpac Private Bank. He advises business owners, investors and affluent Australian families on wealth protection, succession planning and intergenerational wealth transfer

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