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10 Tips to Take More Calculated Risks as a Business Leader

In the culture space, taking risks is necessary if you want to reach new heights.

Ten Culture Council members

Photos courtesy of the members

Taking risks as a business leader can have a significant positive impact on your company if things turn out well, but it can also set you back if you haven’t fully thought through every pro and con.

The practice of calculated risk-taking, however, is essential for business growth. To help, members of Rolling Stone Culture Council shared 10 tips to encourage fellow culture leaders to take more calculated risks and explained why doing so is vital to business success.

Empower Your Team to Fail Fast

Fail fast. Yes, do the research, understand the audience need you are addressing and plan how it will be executed, but also empower your team (or yourself!) to fail. And if you do fail, review, learn, iterate and execute again. It fosters a culture of creative courage and it’s great learning. Michael Klein, Miraculo Inc.

Be True to Your Team

As a culture leader, you have to be true to your team. You want to cultivate those around you to bring out the best in their abilities. You want to be transparent about business practices and movements inside your industry. Ultimately it is your call how to push your business forward, but by having a well-trained and informed team, a calculated risk feels a lot more calculated and a lot less risky. Wes Meyers, Burning Tractor

Listen to Your Gut and Get in the Right Headspace

Nothing exciting happens in your comfort zone. If I waited for the right moment to start my agency or to move out of state, it would not have happened. Listening to your gut is half the battle and the other is being in the right headspace to grow from the change you are about to make. Sarah Sebastian, Rose Gold Collective

Use Your Brand ‘Pillars’ as a Decision-Making Guide

I believe every decision has risk — even the decision to not make any changes. So, I like to create “pillars” for my brands and even myself. If you know what you or your brand is about (three to five non-negotiable things), then use those as your guide to make decisions, especially when it comes to taking risks. If that decision or path aligns with who you or your brand are or want to become, then it’s worth trying! Buck Wimberly, ULAH, LLC / ULAH Interiors + Design, LLC

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Deeply Understand Your Core Audience

Get to understand your audience even better than you do today. Use both intuitive and scientific, data-driven approaches to polish your knowledge of your core audience. Then, if you want to take risks, launch a product that is both attractive to your core audience and to the adjacent target demographic that is similar to your core demographic, but not exactly the same. Vicente Marti, elrowfamily

Think About What You Would Try Without the Fear of Failure

So often we are limited not because of a lack of resources, but by our own fear and self-doubt. Try beginning with a prompt, such as, “What would I love to try if I knew for certain I could not fail?” From there, make a list of three to five actionable steps you could reasonably take toward that goal in six months and identify three people you already know who might be able to help you get there. Lisa Weser, Trailblaze

Understand Why You’re Leading

The best tip I have is to truly understand why you are involved in trying to lead within your culture. Having that authentic connection is important. It will empower you to see opportunities, overcome challenges and take calculated risks because you will be personally invested in the process. Michele Vavonese, Hope Center for the Arts

Take One Step at a Time

If you aren’t seeing the rewards you desire in your life or business, there’s only one culprit: You simply aren’t taking enough risks. Risk is scary because we are taught to consider the worst that could happen. You don’t have to take the biggest risks all at once, though. Take it one step at a time, with a little to lose and a little to gain. From there, you can correct your course and keep moving. Nick Nanton, DNA Films

Get Out of Your Echo Chamber

You need to develop the habit of being an ambassador at all times. Remember that culture travels; you travel. Talk about what you do often and where you feel it might not be embraced (within reason). You may find out the opposite is the case. Michael Polk, Billboardology.com

Test the Waters

Digital marketing is such a beautiful thing because you can spend a little money on advertising, gather data and see if something is resonating with an audience or not. Take this little risk of spending a little to test the waters, and then pour the cash on your advertising campaign when you see it’s working. Make sure to keep monitoring though, and stop pouring cash on it when it stops working. Cassie Petrey, Crowd Surf

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