How to help your team embrace risk

Positive change requires risk, and risk can be scary. Leaders can apply these tips to help people move out of their comfort zone
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crisis leadership

Change is difficult – no matter the size of your company or the strength of your leadership. This is especially true in IT organizations that are beholden to legacy tech or processes. You and your team members are already taking small risks every day. By delegating tasks, prioritizing one project over another, or bringing on a new client, you are gambling that the choice you made will benefit you and your company at the end of the day.

Risk-takers are catalysts for positive change. They are responsible for innovation and advancement far more often than they are responsible for outcomes that hurt the bottom line. I encourage my team to push the boundaries because most executives would agree that not taking any risks is more detrimental to your business strategy than taking the biggest risk you can imagine.

The latter half of 2021 is the perfect time to flex the resiliency muscle we have all strengthened in the last 18 months, as you work to bring your organization to the next level. Here are three ways you can help your teams to get more comfortable taking risks:

1. Set clear expectations

The first step to successful risk management is to define what a “smart risk” means for your team. By defining the parameters of a calculated choice, your team can feel confident stepping outside of their comfort zone.

[ Want more advice on fostering a stronger culture? Read IT leadership: 3 ways to enable continuous improvement. ] 

Brainstorm a list of thoughtful questions to consider as you work through the ideation process. If you find that your team is resistant to change, encourage them to start small. Adrian Otto, technical director at Google, recommends taking incremental risks in his essay Think like a Python, not a Tiger. Over time, these will come to create a greater total risk for your business, but an incremental approach is less daunting than taking it all on at once.

Inevitably, your team will have failures, but as you build your brand it is important to simultaneously create a culture that celebrates setbacks and an environment that encourages people to step out for the good of your organization.

Consider the “blameless post-mortem” approach. This can help your team deeply explore what areas of the project went wrong while acknowledging that everyone on the team had good intentions and made the best choice with the information they had. It can also serve as a written record of tried solutions to save time down the road.

As you grow your business, consider implementing your own review strategy to ensure your team members are all on the same page.

2. Set aside time to be creative

The greatest strength of your employees is not how quickly they can work through a difficult assignment, but their ability to solve problems creatively. Encouraging your teams to think outside the box can yield great rewards when it comes to taking risks. Simply put, the more ideas you have to choose from, the greater the likelihood that one of them will be your business's next great innovation. 

The more ideas you have to choose from, the greater the likelihood that one of them will be your business's next great innovation.

Global powerhouses like Google and Apple set aside up to 20 percent of their employees’ time to focus on projects that fuel their creativity. In his book, Let My People Go Surfing, Patagonia founder Yvon Chouinard preaches the benefits of flex time to help employees maximize their creative potential.

While that may not be possible for every organization, try dedicating time for teams to collaborate without specific business objectives in mind. Set aside one hour every week where each member of your team shares one thing they’ve learned, or introduces a new idea. By taking time to intentionally be creative, you can avoid getting bogged down by the to-do list and encourage discussion that makes your team feel heard.

3. Empower your team to embrace uncertainty

Once you’ve built a strong foundation and are welcoming new ideas, how do you scale your risk-taking and integrate it into your culture? As your team becomes more comfortable taking risks, don’t lose sight of the goal. Talk frequently with your organization’s leadership about where you are headed and be deliberate about communicating that to your team.

Don’t wait until the conditions are perfect, and trust in your ability to pivot when necessary. As a leader, you can instill confidence in your team by practicing resiliency in your own decisions. Stay in touch with your teams and recognize the point where your people are stretched to their maximum potential without sacrificing the quality of your work.

As you embrace uncertainty, you encourage your team to do the same. Over time, your small risks will become less uncomfortable and begin to yield significant results for your organization. Further, you’ll empower your employees to ask insightful questions and carry a risk-taking mindset with them as they build their careers.

[ Get exercises and approaches that make disparate teams stronger. Read the digital transformation ebook: Transformation Takes Practice. ]

Katherine Kostereva is CEO and Managing Partner of Creatio. Creatio is a global software company providing a leading low-code platform for process management and CRM. The company has been highly recognized as a market leader by key industry analysts.