Steve Adubato’s Lessons in Leadership: Leadership Requires Risk Taking

By Steve Adubato, Phd On Nov 25, 2025

In this special “Leaders in Law” edition of Lessons in Leadership, Steve Adubato talks with Thomas Scrivo, Managing Partner, O’Toole Scrivo, about leadership, innovation and launching Liberty Bank of NJ. Then, Steve and Mary Gamba are joined by Ralph Gigliotti, PhD, Assistant Vice President for Organizational Leadership, Rutgers University, and Author, “Post-Crisis Leadership,” about the leadership practices that are critical after challenging times.

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In these challenging and evolving times, it is more important than ever for leaders and managers to encourage their team members to “think and act outside the box.” This often involves creating a culture where calculated risk taking is not only expected, but required, for an organization to move forward and thrive.

When it comes to risk taking, it should not be restricted by an organizational chart or an employee’s job description. Instead, to achieve strategic objectives, such as increasing revenue, improving customer satisfaction, or driving sales numbers, the best leaders find ways to break down silos and get people outside of their lane. The days are long gone of people saying things like, “That’s not my job,” or, “You are the CEO, I am just here to take your direction.”

Let’s consider some tangible ways to encourage risk taking in the workplace:

• Clearly communicate expectations. Too often, employees aren’t entirely convinced that senior leaders want them to take risks. They hear the rhetoric, but they’re not sure that their bosses will stand behind them if the risk results in a poor outcome—especially when it involves money or affects the bottom line. The talk around innovation is easy; the implementation is complex. That’s why it’s vital for leaders to clearly define what responsible risk taking looks like within their organization. Employees need to know where the boundaries are and what kind of experimentation is acceptable. When expectations are transparent, people feel empowered to act without fear of hidden consequences.
• Model the behavior. Leaders who actively demonstrate thoughtful risk taking set a powerful example for their teams. When employees see their leaders stepping out of their comfort zones, making bold yet informed decisions, and being candid about both successes and failures, it builds credibility. Modeling risk taking also helps normalize learning through experience. Leaders can share their decision-making process—what information they considered, how they evaluated trade-offs, and what they learned from the outcome. This transparency shows that taking a calculated risk isn’t about perfection; it’s about progress and continuous improvement.
• Share success stories. People are more willing to take risks when they see that others have done so and been recognized for it. Leaders should highlight examples of employees who have thought creatively, challenged old systems, or introduced innovative ideas that benefited the organization. These stories can be shared through newsletters, meetings, or informal conversations. Equally important is sharing lessons from risks that didn’t go as planned but still contributed to learning or process improvement. When leaders celebrate both results and effort, it reinforces that smart risk taking is valued—not just safe, predictable behavior.
• Alleviate fear. Fear is one of the biggest barriers to innovation. Whether it’s fear of failure, fear of being judged, or fear of overstepping authority, it can quickly shut down creativity. Leaders must create a space where employees feel comfortable expressing ideas and taking chances without worrying about embarrassment or punishment. Encouraging open dialogue, acknowledging effort, and offering constructive feedback can help ease anxiety. Over time, this builds confidence, trust, and a culture where people become comfortable being uncomfortable.
• Provide resources and safety nets. Encouraging risk taking without proper support can backfire, leading to frustration or burnout. Employees need time, tools, and mentorship to test and refine their ideas. Leaders can also create safety nets, such as processes that allow for experimentation without jeopardizing essential operations. Post-project debriefs, start-up funds, and pilot programs can all serve as low-risk ways to test new approaches. Even when outcomes aren’t exactly what was planned, the organization benefits from what is learned.

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