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When to be a lone wolf or choose to work with the herd

We’ve all heard the career tropes about there being no “I” in team and similar. For the most part, I can’t think of a time I’ve heard a motivational speaker encourage people to ignore the rest of the work crew in favor of doing it all on their own.

Not all of us do their best work in group settings (raises my hand), one of the reasons the rise of the remote office and freelancing make the gig economy so powerful and popular. So how do you know when to stick with the rest or when it’s best to strike out on your own?

“Business has many similarities to individual and team sports,” said Drew Westervelt, Founder + COO of HEX Performance, an entrepreneur who played nine seasons of Lacrosse in the MLL, NLL and with Team USA. “You need to clearly understand and perform your best in the role that leads to wins. Whether you have the support of a team or are a lone ranger on the court, the same level of vision, preparation, and commitment is required to battle through.”

Okay, so we know that the analogies work, but how can you determine which team to join and which of the rules to follow? Sometimes it’s literally a matter of showing a willingness to be part of the group, even if part of your work is done independently.

The royal we

Trying to act more like part of the team? Westervelt says “I never like to hear “I” internally during conversations as “we” inevitably will have a hand in the execution. I think it signifies an unwillingness to be open-minded and empathic to accepting other thoughts, idea and support.” Good to know. Sometimes it’s important to try to act like part of the group simply not to be excluded from upcoming projects.

How well do you prioritize?

If you’ve got a constantly updated to-do list in your head, it’s possible you’re best on your own. “One of the most crucial skills that can help people figure out whether it’s best to fly solo or be a team player is the ability to prioritize,” said Mike Lu, CEO of Triller – an AI-powered music video app. “Figuring out how much time is needed and what kind of return you’ll get on every project you take on is a tactic that will help you work smarter.”

Challenge yourself

While a strong team is powerful, Westervelt says “Sometimes have to challenge yourself to think differently from the team.” Why? Because If you rely too heavily on others, Westervelt believes you become a follower. “I’ve learned to believe in what sets me and my business apart. We all have roles in business or on the field. Believe in your ability and have the confidence to make your value be seen by actions to drive your team or business.” But don’t just follow the pack. Westervelt believes that “Me too ideas are never game changers.”

Come for the criticism, stay for the life lessons

Believe it or not, being the lone wolf can sometimes make it harder to move swiftly and effectively because you don’t have input or challenges from others necessary to better yourself and your work style. You might sit around puzzling over an issue when asking a potential team member for advice could change the trajectory of your career.

“One skill that stands out is the ability to accept constructive criticism,” said Westervelt. “Whether on the playing field or business arena, always ask for feedback. Customer feedback in business is similar to watching film in sports. It doesn’t lie.” But don’t expect it to always be positive. “Constructive and real feedback is sometimes hard to listen to, but it always helps build stronger products or services.”

What’s your action plan?

“As a leader, your ideas are nothing but thoughts in your head until you figure out how you can actually execute them,” according to Lu. This involves deciding if it’s possible to execute on your own or if you need a team of five to help you out.

You can’t do it all

One of the problems perfectionists face is the inability to delegate, which usually means they’re trapped in a mire of busy work instead of the things they do best. Westervelt said.

“In my experience, a trusted team is essential to business success. You can’t do it all. Nobody can!” He believes that “You will grow individually when you surround yourself with great people and identify team goals & metrics to achieve those goals.”

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Rachel Weingarten is a marketing & brand strategist and president of 729.marketing. She's a pop culture and trends analyst who frequently writes about business and style and the business of style. Rachel's a sometimes professor, teaching personal branding on the graduate and undergraduate levels. She leads corporate seminars on topics including evolving communication and spirituality in the workplace. Rachel is also the author of three award winning non-fiction books.

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