Permission to Screw Up: When to Set Up the Fireman Safety Cushion

When a team member stumbles, how do we, as leaders, react? Some leaders instinctively jump in to rescue, solving the problem themselves, while others step back, allowing the team member to struggle and grow from the experience. Where should we draw the line?

I once heard about a friend who set up her own business while still in school. Eager and ambitious, she took out a loan to get started. Her father, a seasoned professional, gave her some advice: be mindful of how you spend the money and ensure you check trademarks before settling on a name for the company. She listened, but in the whirlwind of setting up the business, some things slipped through the cracks.

A few months later, she received a legal notice—a company claimed she had infringed on their trademark. Panicked, she immediately called her father, expecting him to step in and help her. But what she heard instead left her stunned: “Take care of it yourself. I warned you about this.”

What made the situation even more incredible to her was the fact that her father was a lawyer—the one person who could have easily helped her navigate this legal issue. Yet he refused, insisting she learn how to solve the problem herself. It became a turning point in her life, as she developed the confidence and resilience to handle challenges independently.

Hearing her story made me think about my own father and how his approach to support was so different. Growing up, he always made it clear that he had my back. No matter the issue, his message to me was consistent: “You can always come to me.” He wanted me to feel secure and to know that I never had to face anything alone. In fact, he often worried more about me hiding my problems than about the problems themselves.

But at the same time, I have wondered: would I have grown differently if, like my “friend,” I was told to solve things on my own? Would I have gained a deeper sense of independence earlier in life? It is a question that has stayed with me.

Now, here is my confession: the friend I mentioned? She is not really my friend. I just came to know her story through Kristen Hadeed’s book, Permission to Screw Up. Kristen shared her experience of setting up her cleaning company while still in college. The story of calling her father for help, only to hear him say, “Take care of it yourself,” was a pivotal moment in her entrepreneurial journey.

This was not the only challenge Kristen faced while building her business. Early in her leadership journey, she lost three-quarters of her team because she failed to value their input and provide the support they needed. That wake-up call taught her the importance of transparency and open dialogue. Over time, Kristen realized that admitting her own shortcomings created a culture of psychological safety—one where her team felt safe to make mistakes, give feedback, and grow alongside her.

This brings me to a reflection on how much space we, as leaders, should give our team members to fail. I had a peer leader who strongly believed in pushing her team to think for themselves. If a team member approached her with an issue they had not thought through—or worse, had not tried to address—her response was simple but firm: “Go back, think it through, and then come back to me when you have a potential solution.”

At first, her approach seemed harsh. She refused to provide answers, even if it meant the team might take longer to resolve issues or risk making mistakes. Yet, what stood out was the culture she built. Her team trusted her, respected her, and consistently performed well.

This approach sat comfortably between two extremes: the overly protective leader who shields their team from all failures, and the detached leader who watches from the sidelines as their team members make costly errors without guidance. Both extremes are problematic. On one end, protecting a team too much creates dependency and stifles creativity. On the other, allowing them to fall too far without support fosters fear and resentment, damaging morale and trust.

By giving her team room to try, fail, and learn—stepping in only when absolutely necessary—she created accountability and encouraged growth. Her team became more capable with every challenge, and they learned to trust themselves and their leader.

A leader’s role is to set up the safety cushion only when it is truly needed—not for every stumble, but to prevent catastrophic falls. This balance gives team members the freedom to take risks, learn from their experiences, and grow stronger through challenges. By giving people "permission to screw up," leaders allow their teams to build resilience, develop confidence, and ultimately reach their full potential.