Flexibility and risk-taking are often cited as essential skills for leaders and professionals navigating today’s ever-changing work landscape. Yet, these skills are deeply rooted in one fundamental element: trust—trust in yourself and trust in others.
As someone who has worked across industries like tech and finance, and now coaches individuals through moments of transition, I’ve seen firsthand how flexibility and risk-taking can transform both careers and organizations. Let’s explore why these skills matter, what holds us back, and how we can strengthen them.
The Foundation of Flexibility
Flexibility is often misunderstood as simply being open to change. But I see it as something deeper: the ability to stay fully present in the moment. It’s about integrating all your past experiences, current context, and new information to make thoughtful, timely decisions.
I call this “dancing in the moment.” It’s not about rigidly sticking to a plan but responding dynamically to what’s in front of you. This ability to pivot, adjust, and remain grounded is especially critical in workplaces today. Research backs this up—88% of organizations now use agile practices, which demand high levels of flexibility from their teams.
But flexibility doesn’t just happen on its own. It starts with building trust in yourself to make the right call and in others to support you when you take a new path. Without trust, it’s easy to fall into the trap of rigidity or hesitation.
The Courage to Take Risks
Risk-taking is often the outcome of flexibility—it’s what happens when you’ve absorbed the information, assessed the possibilities, and decided to act despite not knowing exactly how it will turn out.
Take one of my clients as an example. She was a new manager who struggled with delegation. To her, letting go of tasks felt risky—what if her team didn’t deliver? Together, we worked on small steps. She started by delegating low-stakes projects and gradually built confidence in her team and herself. Over time, she wasn’t just delegating effectively; she was empowering her team and freeing up her time to focus on bigger priorities.
This is the essence of risk-taking: calculated decisions in the face of uncertainty. And it’s not just an individual skill—it’s a competitive advantage. Research shows that companies encouraging calculated risks are 2.7 times more likely to be seen as innovative.
What Holds Us Back
Of course, knowing the value of flexibility and risk-taking doesn’t make them easy. What often gets in the way is self-doubt or fear of judgment. Many of us overthink decisions or cling to familiar paths because we don’t trust ourselves—or those around us—to navigate the unknown.
I once worked with a client from a data-heavy background who wanted to improve her communication skills. What we discovered was that her real challenge wasn’t about structuring her message; it was about trusting that her insights would land. She questioned every conclusion she made, which kept her from presenting her ideas with confidence. Once we focused on building her self-trust, everything else began to fall into place.
This pattern is common. Whether it’s hesitation to speak up in a meeting, reluctance to delegate, or fear of making the wrong decision, the underlying issue is often a lack of trust.
Building Flexibility and Risk-Taking
So how do you develop these skills? The process starts small but can lead to big changes. Here are some strategies I’ve seen work for my clients:
- Strengthen Self-Trust: Reflect on your past successes and remind yourself of your capabilities. Practice making small decisions quickly, like choosing a new restaurant, to build decision-making confidence.
- Trust Others: Keep track of ways people show reliability—this helps shift your mindset and recognize that you’re not in it alone.
- Lean Into Playfulness: Approach challenges with curiosity rather than fear. Play is a powerful antidote to the critical inner voice that often holds us back.
- Start Small: Build your “risk muscle” with low-stakes challenges. For instance, if you’re a manager, try delegating a smaller project first to get comfortable with letting go.
Trust as the Anchor
At the end of the day, flexibility and risk-taking are about trust. Great leaders trust themselves to make bold decisions and trust their teams to carry them out. This balance creates a culture where risks feel less daunting and adaptability becomes second nature.
The real magic happens when self-trust and trust in others intersect. Leaders who have both don’t just make good decisions—they inspire confidence in everyone around them.
As you reflect on your own approach to flexibility and risk, ask yourself: Do I trust myself enough to make tough calls? Do I trust others to help me succeed? By focusing on building trust, you’ll find it easier to adapt, take risks, and navigate uncertainty with confidence.
Because ultimately, the greatest risks lead to the greatest growth.