How to Make Risk Feel Less Risky—And Why It’s Essential for Success

We’re gonna go out on a limb here and say that you didn’t get to where you are without taking a risk. Maybe it was moving to a new city in pursuit of a job opportunity. Maybe it was volunteering to lead a project that had never been tried before. Or maybe it was saying “no” to a lucrative offer because it compromised your long-term goals.

Now that all your risks have finally paid off—now that you’re here—it can be tempting to play it safe. Unfortunately, not taking a risk is sometimes just as risky.

Risk is uncomfortable because we lack information. First, you can’t be sure how people will react to your decision or action, and that can be daunting—will they be supportive or dismissive? Will your company standing suffer as a result? Nor can you be sure how your idea or decision will play out, or what the benefits are, which can be nerve-wracking. But as a leader, there are steps you can take to form a safe experimentation space for your team to create value and spur innovation:

  • Keep your eyes on the prize. Consciously choose growth over stability. Again, it’s easy to rest on your laurels and keep doing the same thing that got you to the point—but in dynamic markets, it’s critical to continue experimenting and building on prior success.
  • Empower voices. It’s all too easy for the same people to dominate the conversation, especially as you go up the hierarchy. Encourage everyone to contribute by using check-ins and rounds to get them in the habit of participating. At the same time, discourage disrespectful behavior. If you notice certain members of your team consistently dismissing ideas or interrupting or talking over others, make sure you address this with them in 1:1s.
  • Make room for failure.
    • Make it safe-to-try. Instead of “risking it all” in a grandiose gesture, test out your idea in situations where, even if everything goes wrong, it won’t result in permanent damage. Before rolling out a new policy to the organization, test it on one department. Before launching a new product, design a “skateboard” to see if it fulfills customer needs.
    • Plan for the worst-case scenario. Do a pre-mortem to think through what could go wrong, and then determine what’s most likely to happen, and what will have the greatest impact. Then, brainstorm ways to either prevent those things from occurring, or develop a plan to address it should those scenarios occur.
    • Build in time to learn. Dedicate time to learning from successes and failures in a non-judgmental way. Hold regular retrospectives to review what works, what doesn’t, and what you can improve for next time.
  • Lead by example. Your team will look to you to establish the norms around risk-taking, so model fallibility and vulnerability. Lead with curiosity and investigate assumptions. Acknowledge what you don’t know, and instead of providing solutions, ask them for their hypothesis.
Published March 20, 2019

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