Try, Fail, Repeat: A Leader’s Roadmap to Success

“Don’t ‘fake it till you make it.’ That’s garbage advice. Face it till you make it. Get up. Work hard. Fail. Stand back up. Face it again. Do a little better. Fail again. Get back up. Repeat.” –Jordan Syatt

Sometimes bringing our best selves into work means we fail. But it’s what we do from there that makes us a great leader. I’d like to tell you about a time where I failed as a manager and what I learned.

I once worked in a retail branch of my organization as a manager overseeing about 10 associates. I was an experienced manager in charge of a new-to-me team. I understood that managing people often involved modifying my communication and even leadership style based on the individual employee – and I was striving to do this. However, there was one associate on my team who I could never quite figure out how to engage in a way that was meaningful for them. They struggled in their role and needed my help along the way.

I now see the missed opportunities to listen to my employees’ concerns, empathize with them and help them visualize what success could look like. Unsurprisingly, this employee left my team soon after, and who could blame them? From their perspective, they had a manager who wasn’t willing to hear their concerns and work with them to improve their performance. From my perspective, I believed my decision to push the teammate out of their comfort zone to complete tasks was a way for them to learn how to metaphorically swim. It wasn’t until later, with some self-reflection, that I understood where my failure was.

As I’ve grown in my leadership over the years, I can look back at moments like this and see it for what it is: me failing to effectively communicate, and not my employee failing me. The sink-or-swim approach can be successful, but only with the right person. I knew that every employee learns differently. I knew that I had to modify my communication and coaching style to help my teammates grow; yet I misinterpreted the situation and the employees’ needs, and it cost me a teammate who may have been extremely successful, given the right environment and a supportive relationship with their manager.

Fast-forward a few years, and I’m the leader of our contact center. That same person applied for an opening I had for a phone agent. They knew I was leading the department, so it should have been a signal to me that they were, in essence, extending an olive branch to give me a second chance as their leader.

Taking risks and learning from one’s failures is an essential part of a leader’s growth path. However, recalling our prior work relationship struggles, I ended up hiring someone new and unfamiliar to me. Looking back on the missed chance to again be a leader for the associate from years past, it could have been an opportunity to grow further in my managing skills, and it wasn’t until much later I came to this realization. A contact center teammate shared with me during a one-on-one conversation that they were afraid to take risks out of fear of unintended consequences. I relayed to them the story above and explained if I had pushed past my fear of being uncomfortable in the short term, I could have taken that experience and reshaped it into a potentially lasting, successful work relationship.

A takeaway from this experience that has helped me to become the leader I am today is even though I may be afraid, I do the thing anyway. Pushing past my fear and taking action has helped me to make more confident decisions for myself and my team. I learn a skill, I try it out, and once I’ve made enough progress on it to feel successful, I can teach it to others.

The contact center industry is continually advancing; new technologies are introduced; for us to remain competitive and relevant, we must adapt and adopt new ways of thinking about the next best way to serve our customers. When I demonstrate that I am capable of taking personal accountability as a leader, I set the example for my team that it’s okay to fail as long as we learn from our mistakes and do better the next time.