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How to make the transition from corporate to startup culture

You’ve spent years playing by the corporate rules, but that all goes out the window when you join a startup. Here’s how to manage.

How to make the transition from corporate to startup culture

You’ve been working your way up at a traditional corporate job for most of your career—15, 20, even 25 years. You know how it works. But now you’ve been hired by a startup that needs your years of expertise, and all the rules seem different.

Many of the workers are younger than you—but with similar titles. The hours may be long, the office may seem bizarre, and responsibilities change from day to day. For senior executives, jumping the corporate ship and moving to a startup can be intimidating, to say the least.

“When you come from a relatively predictable environment, it’s daunting not to know what’s going to happen from one day to the next,” says Alexandra Levit, workplace expert and author of Blind Spots: The 10 Business Myths You Can’t Afford to Believe on Your New Path to Success. “Your direction can change so radically and without warning. You feel like you have to step up your game or perish.”

Before you start wearing Hawaiian shirts and flip-flops to work, try these coping strategies.

Look before you leap

Hopefully, you researched the culture and responsibilities of the company before you climbed on board, so you haven’t been blindsided. If not, check out a review site like kununu, where employees give anonymous feedback about the way things really are (like whether office dogs and lunchtime yoga are part of the perks).

In addition to researching your specific company, you could read up on some books about startup culture, like Zero to One by Peter Theil or Rework by Jason Fried and David Heinmeier Hansson.

“It’s important to understand what a startup culture is like before actually starting a job at one,” Levit says. “Do some soul searching to ascertain if it’s an environment you can stomach.”

Dress your age

One mistake mid-level workers make is trying to adjust their wardrobe to mirror what they’re seeing on younger coworkers. “I think women especially struggle with this, particularly if they’ve come from corporate life,” says Nancy Halpern, an executive coach with KNH Associates in New York City.

While you’ll most likely want to ditch a formal suit (or even suit jacket) in order to adhere to a more casual dress code, stick with what works for you and what you feel comfortable wearing. There’s no need to dress 20 years younger to do the job.

Be collaborative

“Many startups value open opinions, but you can’t let your deeper experience level make you appear like you’re dominating or believing that you know more, even if you think you do,” says Evan Pellett, recruiter and author of Cracking the Code to a Successful Interview.

The startup culture is a lot more democratic and less hierarchical than the traditional corporate setting, so try to take a “less is more” approach and weigh in when you feel like your input could really help—not just to be another voice in the room.

Often, at startups, Pellett says, “Everybody gets one vote at the table and an opinion on things.”

Go with the flow

Mid-level executives are used to being rewarded for playing by the rules, but startups are really shaking up the rules.

“To succeed here, you have to be comfortable figuring out what works and what doesn’t as you go along,” says Jessica Sweet, a career coach for mid-life professionals and executives at WishingWellCoach.com. “No one is going to hand you the rule book. Get comfortable pitching in and doing whatever it takes to make the company succeed.”

This could mean literally lending a hand when the office needs furniture moved, or working on a task a few levels below what you’re used to. Your willingness to be a team player will be valued more highly in this nimble environment.

Say goodbye to 9-to-5

“Mid or senior career level people know about strong work ethic” says Pellett, but you may find that the younger generation gets their work done on their own time, and not necessarily how you would manage it.

Remember, one of the benefits of working at a startup is that you have more flexibility in your schedule (perhaps doing more work from home than at a corporate gig would allow).

Even if you overwork, stay late, or come in before the sun rises, other people may have different work styles—and that’s fine.

Don’t kill yourself socializing

Some execs try to keep the same kind of late social hours as their startup peers, even if they’ve long ago left the 2 a.m. bar scene behind. The truth is, it’s not worth it.

“An occasional visit to a bar and showing your fun side by dancing it up or karaoke is a good thing,” Pellett says. “Doing shots of liquor next to the 20-somethings may not be,” he says.

Find other ways to connect with coworkers outside of work, such as hiking, urban escapes such as harbor cruises, or visits to wineries. This will show people that you care enough to want to be a part of things.

Get comfortable being uncomfortable

Let’s face it—if you’re entering this totally new culture after years in a buttoned-up, predictable corporate world, it’s not always going to feel natural. But with that strange feeling may come some of the benefits that inspired you to make this kind of move in the first place.

“What you get is a much more fluid environment where you can have a higher impact on the people around you and you’re much closer to the work,” Halpern says. “There’s more going on in the day, and you have a much higher energy level. But that may come with continual low-line discomfort because it’s just different.”

So you may not be as comfortable as you were with your “cog-in-the-wheel” place in the corporate machine, but you just might get a bigger sense of satisfaction from what you’re doing each day.


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