Everything I've Ever Done Was Wrong

Embracing Imperfection and the Power of Course Correction

Admitting mistakes as a leader can be daunting, but it’s also one of the most powerful things you can do. Over time, I’ve learned that everything I’ve ever done was wrong in some way—yet, it’s this very recognition that has shaped my journey as a leader. Embracing imperfection and embedding course correction into your leadership style can transform not only your personal approach but the entire culture of your organisation.

The Reality of Imperfection

Mistakes are inevitable. Despite careful planning and strategic thinking, things will go wrong. Variables we didn’t anticipate, miscommunications, and unforeseen challenges are all part of the complex landscape we navigate daily. But rather than viewing these errors as failures, they should be seen as opportunities to learn, adapt, and grow.

When I say that everything I’ve ever done was wrong, I mean that perfection is unattainable. Every decision, strategy, and project has flaws. But these flaws don’t spell failure—instead, they offer pathways to innovation and improvement. Successful leadership isn’t about getting everything right the first time; it’s about how you respond when things don’t go according to plan.

Building Course Correction into Your Leadership Framework

Recognising the inevitability of mistakes is only the first step. The real test lies in how we respond. Here’s how you can incorporate course correction into your leadership style:

1. Design Adaptive Processes: Create processes that are flexible and allow for adjustments. Implement shorter project cycles that include regular review sessions to assess progress and make necessary changes before small issues turn into major problems.
2. Foster a Culture of Feedback: Encourage ongoing, open feedback across all levels of your organisation. When feedback is continuously sought and given, it becomes easier to identify areas for improvement and address them swiftly.
3. Implement Regular Retrospectives: Don’t reserve retrospectives for the end of a project. Instead, make them a regular practice. These sessions allow teams to reflect on what’s working, what’s not, and how to improve moving forward.
4. Encourage Experimentation: Build a culture where experimentation is welcomed, and failure is seen as part of the learning process. Small-scale experiments can lead to big insights, especially when they’re designed to be low-risk and high-reward.
5. Use Data for Real-Time Adjustments: Equip your teams with the tools and data they need to make informed decisions on the go. Real-time data allows teams to correct course before issues escalate, ensuring smoother project execution.

The Role of Leadership in Embracing Imperfection

As leaders, we set the tone for how mistakes are perceived within our organisations. If we treat every misstep as a failure, our teams will become risk-averse, stifling innovation and growth. Instead, here’s how you can lead by example:

• Model Humility: Admit when something hasn’t gone as planned. Sharing your own mistakes and the lessons you’ve learned from them encourages a culture where imperfection is seen as part of the journey, not a dead end.
• Reward Learning, Not Just Success: It’s important to celebrate success, but it’s equally crucial to celebrate the learning that comes from failure. Shift the focus from purely achieving outcomes to valuing the process and the growth that occurs along the way.
• Communicate Clearly: Make it clear that course correction is not only accepted, but expected. When teams know they have the freedom to pivot and adjust, they’re more likely to take proactive steps to improve their work.

Case Study: Overcoming Factional Divides in a New Leadership Team

Imagine a newly formed leadership team in a rapidly growing organisation. The stakes were high, and the team was tasked with driving significant change to ensure the company’s success in a competitive market. However, shortly after coming together, it became apparent that the team was deeply divided. Two distinct factions emerged, each with its own worldview and approach to leadership.

On one side were those who believed in a structured, top-down approach. These leaders had extensive experience in established organisations where hierarchy and clear chains of command were the norm. They valued order, predictability, and control, believing that strong leadership meant setting clear directives and ensuring they were followed to the letter.

On the other side were leaders who championed a more collaborative, startup-like environment. They were driven by innovation, agility, and a belief in empowering employees at all levels. These leaders valued flexibility and were less concerned with formal structures, preferring instead to create a culture where ideas could flow freely and decisions could be made quickly.

The clash between these two factions created a significant challenge. Meetings became battlegrounds where discussions were often more about defending positions than finding solutions. Decisions were delayed, projects stalled, and the frustration was palpable. The team’s inability to work together was not only affecting their own performance but was beginning to ripple through the organisation, leading to confusion and a lack of direction at all levels.

Realising that the status quo was unsustainable, the leadership team faced a critical choice: continue down a path of dysfunction or find a way to bridge their differences. The turning point came when the team collectively decided to embrace the idea of imperfection and commit to a process of course correction.

The Path to Alignment

The first step was to acknowledge the elephant in the room. The team held a series of open and honest retrospectives, where they discussed the challenges they were facing. These sessions were not easy—there were moments of tension and discomfort as team members aired their grievances. However, these retrospectives also provided a safe space for leaders to express their concerns and, crucially, to listen to each other’s perspectives.

Through these discussions, the team began to understand that their differing worldviews weren’t necessarily in conflict but could be complementary if managed correctly. They realised that the structure and discipline valued by the top-down leaders could coexist with the flexibility and innovation championed by the more collaborative leaders. The key was to find a balance that leveraged the strengths of both approaches.

To achieve this balance, the team introduced several new practices:

1. Integrated Decision-Making: Instead of defaulting to one leadership style, the team developed a decision-making framework that incorporated elements from both approaches. For strategic, long-term decisions, they adopted a more structured process, ensuring that all potential risks were considered and that there was a clear plan in place. For day-to-day operations and creative projects, they allowed for more flexibility, empowering smaller teams to make quick decisions and iterate rapidly.
2. Cross-Faction Collaboration: To break down the silos that had formed, the team initiated cross-functional projects that required collaboration between members of both factions. These projects were designed to tackle specific organisational challenges, with the dual purpose of solving pressing issues and fostering better working relationships. As leaders from different factions worked together, they began to appreciate the value of each other’s perspectives, leading to a more unified approach.
3. Ongoing Feedback Loops: The team established regular feedback sessions where leaders could voice their concerns, share what was working, and suggest adjustments in real-time. This ongoing dialogue allowed the team to make continuous course corrections, ensuring that they remained aligned even as new challenges arose.

The Transformation

Over time, these practices began to bear fruit. The leadership team moved from being a fractured group to a cohesive unit. The initial tensions didn’t disappear overnight, but through persistent effort, the team learned to channel their differences into productive outcomes. The structured leaders found that by incorporating more flexibility, they could still achieve their goals while fostering a more innovative culture. The collaborative leaders, on the other hand, realised that a certain level of structure was necessary to scale their initiatives effectively.

The transformation was evident not just within the leadership team but throughout the organisation. As the leaders aligned their approaches, the rest of the company followed suit. Teams at all levels started to adopt similar practices of integrating structure with flexibility, leading to improved decision-making, faster execution, and a more positive work environment.

The case of this leadership team underscores a powerful lesson: embracing imperfection and committing to course correction can turn a potentially destructive situation into an opportunity for growth. By recognising that their initial approaches were flawed and by being willing to adapt, the team not only overcame their divisions but also emerged stronger and more effective as a result.

This experience taught them that success in leadership isn’t about rigidly adhering to one way of thinking. Instead, it’s about being open to different perspectives, recognising the value in each, and finding a way to integrate them into a cohesive strategy. In doing so, the team not only corrected their course but set a new standard for collaboration and innovation within the organisation.

Conclusion: The Journey Towards Continuous Improvement

The notion that “everything I’ve ever done was wrong” doesn’t mean accepting failure or lowering standards. Instead, it’s about recognising that true excellence comes from a willingness to learn, adapt, and improve continuously. By embedding course correction into every project, process, and team dynamic, you create an organisation that is resilient, adaptive, and always moving forward.

As a leader, guiding your team through the inevitable challenges and imperfections with humility and a commitment to growth not only drives better outcomes but also fosters a culture of innovation and trust. The next time something doesn’t go as planned, don’t see it as a failure—see it as an opportunity to learn, adjust, and improve. Through our imperfections, we find our greatest strengths, and in the process, we become better leaders.