CEOs Helpful Unconventional Career Advice!

Follow your passion! Do what you love!

From encouraging job-hopping to avoiding ‘clunker’ bosses, executives in a variety of industries give their best tips for new grads—and anyone hoping for a long career.

Career wisdom can often induce eye-rolls. For more helpful, counterintuitive and specific advice, The Wall Street Journal turned to executives in a variety of industries, from the founder of organic food maker Clif Bar & Co. to the female CEO who oversees brands such as West Elm and Pottery Barn.

Their tips are surprising and, at times, even conflicting. One executive says it’s OK to swap jobs regularly; another suggests digging in to a role. Other wisdom is direct: Don’t act like a phony because people are quick to perceive inauthenticity.

Here, executives’ thoughts on navigating the workplace and establishing yourself in your field:

Barbara Corcoran - CEO, Barbara Corcoran Inc.

Pick your early bosses wisely. A good test: Do you even like them?

Pay attention to the person interviewing you, the one who will be your boss. Then ask yourself: Do you like the person? “The boss makes all the difference,” says real-estate mogul and “Shark Tank” investor Barbara Corcoran. “Every time I had a great boss, I excelled beyond my wildest expectations,” Ms. Corcoran says, “and every time I had a clunker, I hated my job.” A good boss is particularly important early in a career, Ms. Corcoran says. Look for a manager who will not be threatened by you, and will push you ahead, helping you discover what interests you in the business. Ms. Corcoran says there’s no secret to sussing out someone; trust your gut. “Intuition is a wonderful thing,” she says. “We all have it. At 21, we have it.”

Clara Shih - CEO, Hearsay Systems Inc.

Don’t just take the highest-paying offer. For your first job, go for the one with the best role models.

“Your pay in your first job pales in comparison to the satisfaction you achieve over the lifetime of your career--that’s why having that model for what good work looks like is so important,” says Clara Shih, CEO and founder of Hearsay Systems Inc. and a Starbucks board director. Another reason your first manager makes all the difference: They set your frame of reference for everything from what a strong work ethic looks like to how best to collaborate with others. During the interview process, talk to people on your prospective manager’s team and those who have left. Ask about their management style and whether their boss challenges them. “I’ve had some millennial workers who, the first time you give them constructive feedback, they freak out. But good managers give you constructive feedback,” she says.

Laura Alber - CEO, Williams-Sonoma

Dig in. Don’t treat your first job (or second or third) as a temporary stop.

Be committed, says Laura Alber, chief executive of Williams-Sonoma Inc., parent to chains such as Pottery Barn, West Elm and its namesake cooking-goods retailer. It’s easy to spot someone just doing a job as opposed to someone who cares deeply for it, so act “as if this is the only thing that you’re going to do,” she says. “Too many people are always thinking about the next job,” she says. “It’s a very important mindframe to say, ‘Look, I’m going to do this, I’m going to make the most of it -- and how do I make the most of every day?’”

Mandy Ginsberg - Chief executive, Match Group Inc.

No one likes a phony. Don’t be a different person at work.

“People can sniff out BS,” says Mandy Ginsberg, chief executive of Match Group Inc., parent company of dating apps Tinder, OkCupid and Hinge. She advises young hires to be authentic and not to worry about looking dumb. In meetings, acronyms will fly and people will talk about projects without context, so ask questions and insist on details, even if they seem basic. “Be curious and don’t even apologize,” she says, adding that in careers, like relationships, it’s helpful to be vocal about what you want. Desire a raise or promotion? Express that to a manager, even if you won’t get it right away. Ms. Ginsberg says it’s advice she learned from her mother. She’d say: “If you want something, open your damn mouth and ask for it.”

Steve Hafner - CEO, Kayak

Job hop. You’ll be better for it.

“Jumping from company to company isn’t a bad thing these days,” says Steve Hafner, chief executive and co-founder of travel site Kayak, a unit of Booking Holdings Inc. “It helps you grow.” Mr. Hafner says switching jobs broadens someone’s skill set, exposes them to different company cultures, expands their network and helps them advance faster. Kayak has a median employee tenure of three years, a figure he says is good for a tech company. As for knowing when to leave, Mr. Hafner says it’s simple: “When you start to get comfortable in your job and you’re not learning is when you should make that jump,” he says. “It’s pretty straightforward.”

Mark Hoplamazian - CEO, Hyatt Hotels Corp.

Be sensitive. The must-have skill: Empathy.

Being able to understand someone’s experience -- whether it’s a customer or a colleague -- is necessary in every industry, says Mark Hoplamazian, chief executive of Hyatt Hotels Corp. While he believes in the need for agility, quickly responding to changing dynamics in the economy, Mr. Hoplamazian says it’s also as important to develop open-mindedness, sensitivity and the ability to relate to people and their needs. Empathy, in other words, is an essential skill. “Having the capacity to engage with people and understand their perspectives,” Mr. Hoplamazian says, “is really critical.”

Rich Barton - CEO, Zillow Group Inc.

Don’t overestimate the risk of failure.

Be clear-eyed about your real risk profile. What would actually happen to you if you failed? asks Rich Barton, co-founder and CEO of real-estate site Zillow Group Inc. Often, the worst-case scenario is still something you can bounce back from. “We tend to over-ascribe the risk of failing because we’re animals in our primal nature,” says Mr. Barton, who also co-founded Expedia Group Inc. and job-review site Glassdoor. “Many students I talk to, they feel like they’re walking a tightrope, but in reality they have a net just two inches under the tightrope.” While not everyone is so lucky, most people coming out of college have some kind of safety net woven together from a network of friends and family, or mentors and resources from their universities, he says. (Or at least the resourcefulness to build one.) “I always encourage people to dream big, think big, go for it,” he says. “We only have one time around, and you’re not going to die if you fail.”

Logan Green - CEO, Lyft Inc.

Embrace being ‘purposefully direction-less.’ (That doesn’t mean stop working.)

After graduating from the University of California, Santa Barbara in 2006, Logan Green, chief executive of Lyft Inc., found himself in a tough place. “It was actually a really difficult year for me,” he says. “I wasn’t sure what move to make, and what field to commit to.” The lesson, he says, is for new graduates to be “purposefully direction-less.” Try many pursuits, but then settle on one that suits you. “It doesn’t mean you’re not working,” he says. “Embrace and be purposeful exploring what’s interesting to you.” Then, stop doing other things. “People are scared to commit all in on something. When you commit all-in, you’ve got to close a lot of other doors, and commit so hard to something you’ll go all-in to achieve it. If you’ve locked in on what that goal is, you don’t want to question it for years and years at a time.”

Gary Erickson and Kit Crawford, - Co-CEOs, Clif Bar & Co.

Realize the power in saying “no.”

Before taking a new role, particularly one you may be ambivalent about, ask: “What if I didn’t take that job? What if I tried something else? What’s the downside?” says Gary Erickson, co-chief executive of energy bar maker Clif Bar & Co. Both Mr. Erickson, and his co-CEO, Kit Crawford, say they followed unconventional career paths, ones that included owning a bakery (Mr. Erickson) and working in Yosemite National Park (Ms. Crawford). There can be power in saying “no” and exploring alternatives, a lesson both executives know well. In 2000, Clif turned down a $120 million sale to Quaker Oats, choosing to stay private. The sale would have meant $60 million for Ms. Crawford and Mr. Erickson. The company remains family- and employee-owned today. “I get cold sweats thinking, ‘What if I would have taken that money? I would have been so depressed right now,” Mr. Erickson says. “We would have lost our purpose.”

Published By: Bellaland, Wall Street Journal - Chip Cutter, Vanessa Fuhrmans

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