Embracing Failure as a Path to Success in Tech Leadership

Embracing Failure as a Path to Success in Tech Leadership

When Failure Became My Greatest Teacher: A Tech Leader's Journey


In the ever-changing world of technology, the only constant is change. With over a decade of experience in the tech industry, I've faced the challenges of being both a hands-on developer and a team leader. Today, I wish to share a tale of failure, learning, and growth — a chapter from my journey that profoundly shaped my approach to leadership.

The Pivot That Tested My Mettle

I had recently joined a multi-disciplinary software development team as a lead. After a month or two in the team I was approached by some of the front-end engineers to discuss the use of legacy tech in one of our client projects. After a fairly brief set of conversations over the course of a week, I agreed with the idea and tasked the team with pivoting our front-end technology from C#/Razor to React.js. Our goal was straightforward: enable our team, consisting of front-end and back-end engineers, designers, QA, and CRO analysts, to work with modern frameworks and deliver value to our customers more efficiently.

The Misstep

My background was firmly in back-end development, and admittedly, my understanding of the subtleties of front-end technologies wasn't as comprehensive as it ought to have been to make the decision. This gap in my knowledge led to an underestimation of the effort and costs associated with the pivot. Transitioning to React.js necessitated additional infrastructure and brought unforeseen challenges such as the absence of Server-side Rendering (SSR), which adversely impacted our SEO efforts. The team also had a mixture of AWS infrastructure skills within the team, so we also had a hard dependency on our DevOps Principal Engineer who was a floating resource and already assigned to another team.

The Ripple Effect

Initially, the team warmly embraced the changed due to the excitement of working with new tech. However, as issues emerged, a cloud of uncertainty descended over our efforts. Increased tensions, project delays, and escalating costs attracted scrutiny from company leadership, customer account managers and the customer themselves. The team, once buoyed by the promise of innovation, now struggled with a sense of failure. This was a hard-hitting moment for me as I had gone from feeling like a real enabler for my team, to suddenly putting them in a position of imminent doom with a shadow cast over their credibility.

The Moment of Realisation

The turning point came amidst a series of relentless challenges. It was evident that the planned smooth transition had devolved into a series of obstacles, affecting not just our team but also our customers and stakeholders. My decision, made with incomplete information, had set off a chain reaction. On one hand I had to handle the relationship with the customer to provide them with an understanding of why the pivot was still a good idea and in their best interested (as well as my team's). On the other, I had daily battles with technical issues that seemed to keep cropping up once we finally felt like we were getting somewhere.

Lessons Learnt

This experience was a crucible for my development as a leader. It taught me the value of exhaustive questioning and seeking multiple perspectives, especially in areas outside my core expertise. Today, I approach decision-making with meticulousness, consulting technical and business domain experts and ensuring a comprehensive understanding before making pivotal decisions.

It's easy to be super hard on myself when using the power that is hindsight, but I truly believed in that moment that I had done enough to allow me to give a yes or no. With that said, the real benefit here is the post-failure reflections to allow great learning and to avoid making the same mistake twice.

Advice for Fellow Leaders

To my peers in leadership, I offer this advice: Thoroughly understand the risks before making significant decisions. Engage with your team early in the decision-making process, and complement their insights with your research. And most importantly, embrace failure as a learning opportunity. Reflecting on and sharing these experiences not only aids your growth but can also guide others.

If you work for a larger company with multiple engineering teams, use something like an engineering/operational excellence review session or tech all hands to share your learnings. Although it can be hard to hold our hands up to say "I failed", the benefits it can bring to the wider cause are immense.


In the ever-evolving landscape of technology, failures are inevitable. They are the stepping stones to greater understanding, resilience, and ultimately, success. As leaders, our ability to learn from these setbacks and guide our teams through them is what truly defines our journey.