I learned a lot about what makes for a good leader at a recent large inline skating event. I had volunteered to lead one of the skating events for the Big Apple Roll, which entailed getting 75 skaters safely through 20 miles of NYC streets. A seasoned skate leader planned the route for me and offered me pointers along the way, but keeping everything together rested primarily on my ability to delegate smaller tasks to others – it’s clear that this skill is necessarily in any leader.

To explain why, let’s start with a different kind of skating group – one with just a handful of similarly skilled skaters. In this case, everyone can simply follow the guy in front. This “leader” doesn’t need to do much more than follow the route and turn around on occasion to make sure everyone is still there. In essence, that’s not much leading; each person is fine with just following the “leader” (I should note that this leader still has the important task of selecting a safe route and pace). Now contrast this to a much larger group with skaters of varying skills; things are different. The leader has to make sure that skaters know where to turn and keep them on route. This becomes difficult as the group of skaters will inevitably become spread out among several blocks (many more when there’s 75 skaters). The leader must also make sure skaters remain courteous to pedestrians and cars. At this point it’s clear that more than one person is needed to coordinate this sort of effort. It’s here that a leader’s purpose becomes obvious; for his task is coordinating the coordinators – delegation.

The coordinators would each have a set of smaller, manageable tasks. In the case of this skating event, they had to stay in the front with the leader (me) and be ready to mark any turns when I requested them to do so, and stay there until the last skater passed by (which was another coordinator assigned to sweep). These team members also had to keep skaters from taking over the entire road or crosswalks. So a crucial part of the leader’s job is to select coordinators capable of handling the subtasks (and of course knowing what subtasks are required). I had to pick a team of volunteers that I could trust to do the job, without the need to watch over them. In the end, the responsibility rests on the leader. If any single member of his team fails to deliver, it’s still the leader’s fault for not selecting someone capable enough.

The skate event I lead was a successful one and everyone thanked me for it afterwards. Still, the thanks should go to the whole group of volunteers. They were capable, responsible, and enthusiastic in helping out me and the rest of the skating community.

There were two lessons learned on leading: First, that a leader serves to coordinate others when a task is too big to handle alone. And second, that those selected by the leader are picked for specific abilities and should work to live up to those expectations. Although I learned these lessons through involvement in the inline skating community, it’s clear that they apply everywhere, from political offices to workplaces.

Special thanks to Leo for planning the route, sweeping, and giving me guidance throughout this skating event. Also thanks to the skate volunteers that helped out on this event! Lastly, thanks to everyone else on this skating event for supporting the adventure!