Risk-taking is a crucial element in fostering innovation and growth within teams. This article presents valuable insights from experienced leaders on how to encourage and support risk-taking behavior. Discover practical strategies to create an environment where team members feel empowered to take calculated risks and drive positive change.
- Model Risk-Taking Behavior as a Leader
- Reframe Failure as Valuable Learning Experience
- Create Safe Spaces for Innovative Thinking
- Build a Culture of Courage and Growth
- Foster Trust to Encourage Experimentation
- Explicitly Communicate Support for Risk-Taking
- Collaborate on Experimental Ideas with Team
- Lead by Example in Taking Risks
Model Risk-Taking Behavior as a Leader
Encouraging risk-taking starts with creating a culture where failure isn’t a dirty word but a stepping stone. Leaders need to model this behavior themselves by openly discussing their own mistakes and what they learned from them. I often remind teams that investor readiness involves testing assumptions and iterating — we expect some ideas won’t land perfectly on the first try. One of our clients, a startup CEO, made it a habit to celebrate “learning moments” after every project, whether the outcome was success or not.
This shifted the team’s mindset from fearing failure to valuing experimentation. Leaders can also provide psychological safety by making sure no one is blamed for honest attempts that don’t pan out, which I’ve seen unlock creative solutions faster than any top-down directive. Personally, I’ve found that framing risk-taking as a necessary part of growth helped me push beyond comfort zones, and that attitude slowly became part of our DNA.
Supporting small, incremental risks rather than big leaps all at once also eases the team into a more innovative rhythm. In short, leaders who show vulnerability, reward curiosity, and maintain a clear vision for why experimentation matters are the ones who build teams eager to try new things — even when failure is on the table.
Niclas Schlopsna
Managing Consultant and CEO, spectup
Reframe Failure as Valuable Learning Experience
In our experience, fostering a culture of experimentation begins with openly acknowledging that failure is part of the innovation process. We encourage our team to try new ways of delivering content, like using AI-driven personalized learning paths, without the fear of failing. The idea is to gather insights from each attempt, whether it succeeds or not.
For instance, when we launched a pilot program using adaptive learning technology, we did not hit the mark initially. However, through iteration and reflection, we were able to enhance the platform, eventually providing a more tailored learning experience that improved engagement across all levels.
Christopher Pappas
Founder, eLearning Industry Inc
Create Safe Spaces for Innovative Thinking
One thing I’ve learned in over a decade of leading teams is that if you want people to take smart risks, you have to show them that failure isn’t fatal. In our software development teams, we set aside time each quarter for what we call “no-judgment sprints.” The goal isn’t a perfect outcome; it’s a testbed for new ideas that may or may not work.
But here’s the key: I publicly share what didn’t work from those sessions, including my own missteps. When the team sees leadership owning failure without excuses, they stop hiding their own. That honesty creates safety. And once there’s safety, people get creative.
One developer once proposed a completely different workflow for code review. It failed badly, but the process sparked two changes that stuck. That’s how experimentation works. You don’t always get what you expect, but if you build a culture where learning matters more than ego, you still move forward.
Risk-taking needs a soft landing. It’s not about throwing people into the unknown—it’s about building the net underneath.
Vikrant Bhalodia
Head of Marketing & People Ops, WeblineIndia
Build a Culture of Courage and Growth
Creating a culture that embraces risk-taking isn’t just beneficial—it’s essential for innovation in today’s rapidly evolving logistics landscape. I’ve found that supporting calculated risk-taking starts with reframing how we discuss failure.
Instead of viewing failures as catastrophes, we treat them as valuable data points. When our team attempted to implement a new dynamic routing algorithm for optimizing warehouse picking paths, the initial results fell short of expectations. Rather than shutting down the initiative, we celebrated the insights gained and pivoted to a modified approach that ultimately reduced pick times by 31%.
Leaders must demonstrably take risks themselves. I make a point of sharing my own missteps with the team—like when I insisted on a particular warehouse layout that proved inefficient. By openly acknowledging my error and collaborating on solutions, I showed that vulnerability isn’t weakness but strength.
Practical protection mechanisms are crucial too. We’ve implemented “innovation sandboxes” where teams can experiment with new fulfillment methodologies in controlled environments before full-scale deployment. This creates safe spaces for bold thinking without jeopardizing client operations.
Jeff Bezos at Amazon exemplifies this leadership approach brilliantly. His perspective that Amazon is “the best place in the world to fail” has enabled revolutionary developments like AWS and their fulfillment automation. His willingness to support the Fire Phone despite its market failure demonstrated that even unsuccessful ventures generate valuable learnings.
The 3PL industry specifically benefits from calculated risk-taking as consumer demands evolve rapidly. By encouraging experimentation, you create resilient teams capable of adapting to disruption rather than being overwhelmed by it.
Remember: in our industry, the biggest risk isn’t occasional failure—it’s the certainty of obsolescence if you never dare to innovate.
Joe Spisak
CEO, Fulfill(dot)com
Foster Trust to Encourage Experimentation
Innovation requires more than vision. It demands risk. Yet in many organizations, risk is praised in theory but punished in practice.
One of the most defining seasons of my leadership journey came when I served as the chief executive of a large, complex public enterprise. From the beginning, my board made something crystal clear: “We hired you to lead boldly. Don’t play it safe.” That wasn’t just approval. It was an invitation to build a culture of courage.
Because of their posture, calculated risk-taking became our operating norm. We were not afraid to try bold ideas before perfecting them, moved with a calm urgency, and scaled what worked. The board didn’t expect perfection. They expected thoughtful action, continuous learning, and growth. When things didn’t go as planned, we weren’t blamed. We were asked, “What did we learn?”
That clarity changed everything.
A shared mindset emerged: failure wasn’t fatal. It was the First Attempt In Learning. Our leadership team felt empowered to test, adapt, and improve. Conversations shifted from, “Can we?” to, “How might we?” and innovation accelerated.
It was energizing to lead in a space where big thinking wasn’t just allowed. It was expected. Our teams collaborated across our organizations and made smarter decisions aligned to our strategic goals. The freedom to take risks gave people the courage to contribute at a higher level.
The key lesson? A leader can’t carry risk alone. Boards and executive teams must actively model the behaviors they claim to value:
- Champion bold thinking even when outcomes fall short.
- Normalize post-project learning conversations.
- Promote a culture where failure is an opportunity to learn. This creates the conditions for high-functioning, synergistic teams.
When innovation time is protected and taking calculated risks is expected, momentum builds. I’ve worked in environments where risk was feared and others where it was fuel. The difference always started at the top. When your board backs you fully, you don’t just lead differently. You build something that lasts.
Gearl Loden
Leadership Consultant/Speaker, Loden Leadership + Consulting
Explicitly Communicate Support for Risk-Taking
We work in an environment where creativity and experimentation form the foundation of everything we do—from web design to branding. However, creativity cannot thrive in an atmosphere of fear. One crucial lesson I’ve learned is that if you want your team to take risks, you need to normalize failure as part of the process, not as the end of the road.
We foster a “test small, fail fast” culture. For example, when one of our designers wanted to try a completely unconventional layout for a client in a traditional industry, we didn’t dismiss the idea. Instead, we developed a parallel concept, pitched both, and surprisingly, the client chose the bold one. Even if it hadn’t been successful, the learning experience would have been valuable. The point was to provide that creative freedom, assuring the team they wouldn’t be penalized for trying something new.
A person I’ve always admired in this field is Ed Catmull from Pixar. He openly discussed creating a culture where people are allowed to fail safely. His leadership wasn’t about getting everything right but about encouraging the team to keep trying until it felt right. That mindset has influenced how I strive to lead as well.
Risk-taking doesn’t have to be reckless. When people feel trusted, they are more likely to experiment. And when they experiment more, innovation naturally follows.
Juzer Qutbi
Co-Founder, Saifee Creations
Collaborate on Experimental Ideas with Team
Sometimes you have to be straightforward with things like that. Tell your team directly that you’re okay with them experimenting or taking risks – and that you actually want them to do so. Many people simply won’t do these things unless they are explicitly told to do so, since they don’t want to mess with anything risky. They don’t want to risk their jobs!
Seamus Nally
CEO, TurboTenant
Lead by Example in Taking Risks
Lead by example. People are far less likely to take risks and experiment when their leaders never do those things. Even if a leader says they encourage risk-taking, do they really mean it? If you are a leader and you don’t know how to lead by example in this way by taking risks of your own, you can do things like working with your team members who suggest experimental ideas. By working with them, you share the responsibility and demonstrate that you are also willing to take risks.
Mike Fretto
Creative Director, Neighbor