5 Ways To Help Your Team Take Risks


risk taking


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Maureen Berkner Boyt10
May 25, 2024 at 10:40AM UTC
Has your team been heeding Eleanor Roosevelt’s advice to “Do one thing every day that scares you”? Have you?
The good stuff in our careers, those big leaps forward, aren’t going to happen unless we’re willing to take risks. We have to be willing to do something that scares us to get the big rewards. That’s the key.
If you want your team to grow fast, it’s not going to happen if they’re playing it safe. A key strategy for kicking it into high gear is getting your team out there on what I call the skinny branches. You know the place I’m talking about. The high-risk, high-reward, I’ve-never-been-here-before domain.
For those willing to go there, it’s really an extraordinary place to learn and grow. It’s a place high performers seek out and spend a LOT of time in.
If you want your employees to take risks you must create a totally different paradigm for fear and failure. You need your team to understand that high performance involves being comfortable with taking risk and failing into success; that failure is a part of the growth and success equation. Nobody gets it right every, single time unless they are doing exactly the same things in exactly the same ways that they always have. That’s a pattern of stagnation. It’s very predictable, and will get you exactly nowhere.
Help your employees get out there on the skinny branches and stretch themselves. Here’s how:
1. Frame up risk and failure as career accelerators, rather than as something you should spend energy trying to avoid. Create an understanding that risk and failure are simply an expected part of the process of growth and if you’re not failing, it’s an indication that you’re not growing. Be very vocal and visible about your own risks and failures and model the way. If you’re not taking risks and sharing your failures, don’t expect your team to get out on the skinny branches, either. Show them how to risk and fail frequently, fast and forward.
 2. Remind your employees that the timing will NEVER be just right to take risks. We have to do things that make us uncomfortable and that includes taking a risk even when we don’t think we’re ready. The stars are never going to line up perfectly and there’s no such thing as a foolproof plan.
 3. Teach your team to plan for the worst-case scenario. Create a tool that your team can use to help them move forward on a risk they are thinking about taking. Create a document with three columns. In column one, they’ll note what they think the worst-case scenario is if the risk they take goes wrong. In column two, how they’d know they’d gotten there/indicators they have reached the worst case. In column three what action they will take if the worst-case scenario occurs.
Using a tool like this is almost magic. It allows your employees to think through what could go wrong, what their trigger for taking action will be, and what they’re going to do if it happens. Once they’ve created a worst case scenario plan, it allows them to move forward because they’re armed with a plan of action instead of spending mental energy worrying about ‘what if’.
4. Host a lunch/happy hour in honor of your employee’s biggest screw-ups. Own, celebrate, laugh, and discuss when things didn’t go as planned. Share what was learned and how the ‘failure’ has helped move the team forward. When you’re asking people to take more risks, it also means that there will likely be more failure. If your team knows that isn’t going to get them in trouble, but rather will be celebrated,
5. Do a debrief on the things that the team has initially categorized as a ‘failure’. Answer these questions: What went right? What did we learn? How did we just fail forward toward success?
It’s fairly easy to create a ‘skinny branches’ culture. That’s especially true if you allow your team to laugh and enjoy the process, too.
Mo is the Founder of The Moxie Exchange, a training and peer mentoring organization for companies who want to recruit, develop, promote and retain women and create inclusive workplaces. She’s an advisor to CEOs of the nation’s fastest growing companies and is the founder 5 successful businesses. She also been known to sing loudly, dance badly and curse like a sailor.


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