How Candid Can You Really Be With Your Boss?

Marchiano Loen stared at his screen for two hours. He drafted one response, then another. He begged someone in human resources for help. Still, the question vexed him.

What can your manager improve on?

“Oh God, I actually have to answer this,” the tech worker thought as he pondered the employee survey. “What am I going to write?”

Bosses claim they want honest feedback. Telling the truth can spark change, make your work life better and show off your own assertiveness. Or you could get fired. (At least it feels that way.)

Like it or not, silence isn’t an option. But you have to be really careful about just how candid to get with the boss.

Loen says he was once frozen out by a manager after suggesting he could improve his communication style during presentations. Warm small talk and jokes evaporated, and Loen’s big projects were redistributed.

Now he uses what he calls “the Jacuzzi approach.” He dips a toe in with bosses to test the water, seeing how they react to a fairly neutral piece of commentary before saying anything of substance. He might ask, would that meeting be better on Tuesday than Monday?

“It’s a survival mechanism,” he says.

The lies we tell

The average person lies three times in the first 10 minutes of meeting someone new, according to research from Robert Feldman, a professor of psychological and brain sciences at the University of Massachusetts Amherst. Such superficial fibs lubricate many of our social interactions, he says, helping us fit in and getting people to like us.

This salad is delicious, we insist. Or I loved the “Barbie” movie, too! With the boss, the photo of their kid is suddenly extraordinarily cute, their jacket perfect for today’s presentation.

“At the end of the day, we want to hear good things,” Feldman says. “Your boss is just like everybody else.”

What about when bosses want to be tapped into what’s really going on, too? After all, you’re the one who’s connected to collegial chatter and gossip, which can give managers insight into how they can do a better job and get ahead. Giving the right information to your boss can help you, too. You just have to share it the right way.

“I want people to feel like they can be them,” says Karin Storm Wood, who manages a team of communication professionals at a private school. But, “I don’t want everything.”

Don’t assume you have all the facts, she says. Acknowledge you’re just sharing one person’s perspective. And keep your language grounded. For instance, describe a behaviour instead of lobbing a negative adjective at your boss.

Wood says she’s OK with hearing that she sometimes jumps around from idea to idea in brainstorming sessions. She doesn’t want you to call her “scattered.”

“That’s like, ‘Ouch,’ ” she says. “It has that element of judgment.”

Feedback, please!

Everyone seems to want our take these days. We’re subjected to quarterly 360 reviews, weekly pulse surveys and drive-by requests for input by the coffee machine. It’s part of a longstanding shift from command-and-control leadership styles to more collaborative ways of running companies, says Doug Stone, who teaches conflict management at Harvard Law School and co-wrote the book, “Thanks for the Feedback.” A lot of it stems from employees who have demanded more of a voice…even if another app wasn’t what they had in mind.

Be careful what you wish for.

“You have to say something,” says Matt Abrahams, who teaches at the Stanford Graduate School of Business and has a book coming out this week about spontaneous communication.

A smart start is to ask some questions of your own to the boss, says Abrahams. What kind of guidance do they typically find useful? If they readily divulge a time they messed up or made a change, be more candid, he suggests.

Emphasising the positive might subconsciously correct the negative. For example, praising the boss for being so focused at the start of her speech could imply that she completely lost her train of thought by the end, without you having to spell it out. But don’t get too soft, Abrahams warns, devolving into coded language and euphemisms.

“You’re being coy. You’ve got something to say but you’re not saying it. That can look really bad for you,” he says. After all, we were all hired to be experts in our jobs.

The risk of always saying yes

Earlier in his career, Irvan Krantzler used to nod his head yes to everything, eager to fit in. That project idea? It sounded great. A deadline next week? Sure, he could handle it.

The result, he says, was often “bad news, late.” The issue he didn’t speak up about—an unrealistic timeline, not enough people on the team—would fester and eventually send a project sideways.

“I can’t be put in a situation where I can’t be open with people,” he says he realised. He started voicing his concerns more, and left one employer where everyone was expected to agree all the time.

When Leslie Venetz’s boss asked her what she thought about a new team of salespeople, she assumed the pair were just spitballing thoughts in confidence. A few months later, her comments were shared with HR, she says, and a person she had identified as weak was fired.

She felt guilty and betrayed, and soon left the company.

Now when clients of her sales training and consulting firm request her feedback, she asks how they’re going to use it. Are they deciding the fate of a division this week? Or just considering a possibility, and gathering dozens of opinions in the meantime?

The answer, she says, determines her candour.

“Everyone says that they want feedback,” she says. “There’s something to be said for taking a moment.”

Colin Saint-Vil got his money education at the dim sum cart, over a steamy plate of pork buns and turnip cake.

A friend offered to pick up the whole tab on her credit card, “for the points.” At the time, six years ago, “for the points” meant nothing to Saint-Vil, now a 30-year-old planning manager in Brooklyn, so he pressed for more details. They lingered over the dim sum meal as a larger conversation unfolded about annual percentage rates, credit-card debt, payment schedules and more.

Millennials and members of Gen Z prefer to seek financial advice from each other than from parents or from financial professionals. They don’t like overwhelming spreadsheets and marketing material written in seemingly foreign languages. They don’t trust big banks and institutions trying to sell them on investment strategies—as many were raised around the late 2000s financial-crisis. And, they are not wrong: There is a lot to be learned from comparing numbers with peers—from sharing salaries to talking out big decisions like home or car purchases.

Saint-Vil said when his father was his age, he had already begun investing in real estate, but with property prices now so high and mortgage rates only just beginning to fall, he said he couldn’t imagine being able to follow in his father’s footsteps. He, like many millennials and Gen Z-ers, describe their finances as “fairly good” these days, though they hold a negative picture of the greater economy, according to a new poll of 18 to 29-year-olds from the Institute of Politics at Harvard Kennedy School.

Millennials are still reeling from the impact of back-to-back recessions, all while large bank closures and investing scams dominate the headlines. Younger people report a feeling of “financial avoidance” exacerbated by high inflation and the pandemic-era budgeting.

As of June 2023, Gallup polling revealed a historically low faith in U.S. institutions, with younger generations voicing high skepticism. According to Gallup, only 9% of respondents aged 18 to 34 expressed “a great deal” of confidence in banks; meanwhile, 47% and 28% said they have “some” or “very little,” respectively.

But when it comes to winning back young consumers, these same financial institutions haven’t quite given up, and are rolling out new outreach programs and robo advisors, some of which have helped bridge a connection with Gen Z and millennials, said Keith Niedermeier, clinical professor of marketing at Indiana University. But many young people still say they prefer do-it-yourself investing platforms like Robinhood and Acorns over traditional advisers at more established wealth-management firms.

Andrew Ragusa, a real-estate broker based on Long Island, blamed the twin problems of low housing inventory and high home prices for postponing younger buyers’ ownership. The median age of a first-time home buyer in the U.S. is 35-years old as of 2023, according to data from the National Association of Realtors. That is slightly down from an record high of 36 in 2022, but still two years older than the median age in 2021, which is representative of an ageing first-time buyer trend.

When he talks with younger clients now, he detects a gloomy sentiment. “They try to be optimistic, but the overall sentiment is ‘This is supposed to be the American dream: we get a house and we get some financial security and I just have to have faith it will all work out in the end.’ But they don’t have faith it will.”

Fear and shame around being able to buy or accomplish as much as one’s parents might have financially can crop up when millennials talk to elders about their financial frustrations, said Jodi Kaus, director of Kansas State University’s student financial planning centre, Powercat Financial. She’s found that lessons and advice from friends are often more constructive.

Kaus leads a peer-to-peer financial planning centre that pairs up students to work through financial issues. She works to pair people with similar backgrounds: graduate students with graduate students or international students with international students. Talking with someone only a few years removed from your current situation means you’re better able to internalize the messages and execute on their advice, Kaus said.

“Early on, parents even say ‘Are you sure students can help my child?’” she said. “And I say ‘I am more than confident that they can help each other.’

Sharing money tips and financial know-how with your friends doesn’t only benefit the asker, Kaus said. In the Kansas State University peer-to-peer group, the advice giver also learns a lot from their own position, because sharing their story and bonding with a peer helps them to build their own confidence and belief in their financial acumen.

Lindsay Clark, a 34-year-old director of external affairs in Washington, D.C., recalls one lesson she shared with a friend carrying student loans from pharmacy school. Clark works at Savi, a student loan platform, and she offered to cook her friend dinner while they sorted through his loan repayment options. Long after they’d cleaned their dinner plates, they sat together at Clark’s kitchen island, lingering over a plate of homemade hummus and chatting about everything from financial goals to Costco card benefits.

“Those conversations blossom from the transparency, and the visibility makes both people feel really good,” she said. “That creates better relationships overall.”

When you’re talking about money issues with friends, Clark said, you’re not artificially inflating your salary or pretending to know more than you do. And most important, you’re not worried about their ulterior motives.

“You feel safe in that conversation, knowing their intentions are good and they’re not trying to make money off of you,” she said. “And that’s going to lead to better results, because we’re working with the reality here.”

Skepticism of pronounced experts and criticism of established financial institutions is especially common among millennials and Gen Z, Neidermeier said. Studies show people across generations are much likelier to take a friend or colleague’s recommendation to heart over that of a faceless institution, he said; people who spend time on social media just have a greater opportunity to source those answers and field questions.

“What people say to each other over the picket fence is what is the most influential,” he said.

At a certain point, however, talking solely to friends and peers for your financial lessons can be very limiting, said Sarah Behr, founder of Simplify Financial Planning in San Francisco. Relying on your social circle can also put a strain on those relationships; no one wants to be responsible for your disappointment when a financial decision that worked out well for them doesn’t fit as well in your own life.

Behr recommends tuning into your own emotional reactions when assessing peer advice: does the road map they followed align with your own financial values? Does it put pressure on you to live outside your means or challenge your personal risk tolerance? If the answer doesn’t feel clear, that could be a time to outsource to a financial professional who has no emotional connection to you or your financial status.

“‘People have been telling me do this, but I just don’t know if it’s the right thing for me’—I get a lot of calls like that,” said Behr.

Saint-Vil said he and his friends share tips on what high-yield savings accounts offer the best rates, and when he did his credit card research, he chose a card recommended by a friend. When it comes time to work with a financial adviser or even one day a wealth manager, he’ll likely work with someone recommended through a peer. Behr said close to 90% of her business comes by way of client referrals.

Since that first conversation over dim sum, Saint-Vil has thrown his own card onto the table at meals and shared his knowledge with other pals who look confused.

“I have a real wide range of friends who are in many different financial places, but I would say a rising tide lifts all ships,” he said.

Julia Carpenter is the co-author, with Bourree Lam, of The Wall Street Journal’s “The New Rules of Money: A Playbook for Planning Your Financial Future,” a personal-finance workbook published this week by Clarkson Potter, an imprint of the Crown Publishing Group.

How Candid Can You Really Be With Your Boss?

How to deal with the trickiest phrase you can hear from a manager: I’d love your feedback

The lies we tell

Feedback, please!

The risk of always saying yes

Millennials and Gen Z are turning to peers instead of professionals for financial advice. They don’t trust banks, and they are tired of information overload.