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  • Writer's pictureNick Caldwell

On the edge of leadership

The day I learned what separates managers from leaders

A panel from Minus by Ryan Armand. The single greatest webcomic ever.

Way way back when I was a newly-minted engineering manager, I worked on an incredibly frustrating team. We were overloaded with sustained engineering tasks and technical debt. The product managers were struggling to generate a clear road map. The culture was conservative and increasingly-political. The one bright spot was that we had just an insane wealth of talent — former Microsoft Researchers, devs from MIT/Stanford, all passionate and creative folks.

I’ve got an incredibly entrepreneurial spirit, so managing in this environment tore me up on the inside. I saw the potential for what we could be, all the friction getting in the way, and no one “in charge” stepping in to do anything about it. I stressed about it every minute at work, whispered complaints to my close colleagues, and slowly — over months of time — this problem was just eating away at me.

One day, after a particularly difficult all hands meeting where we announced a 3 months schedule slip, I reached boiling point and barged into my friend Ravi’s office for an epic rant. Ravi was an experienced manager and had been something of a mentor to me for years. I will never forget the conversation we had. As I outlined the troubles of scheduling innovative work, the lack of vision, the team culture problems, the horde of ineffective PMs, and my belief that no one in management was doing anything to help, a grin slowly spread across his face. He listened patiently, nodding at the appropriate times, while I had my say. When I’d finished, he calmly fixed me with a firm stare and leaned forward in his seat. “Nick, today I want to teach you the most important lesson you will ever learn about being a leader. Up until now you’ve been a manager. You wait for work, dole it out to your team, and keep the trains moving on time as if all that mattered were schedules and burn-down charts. You have been a fantastic manager. You can get things done! But this is not leadership, not really. Listen to me clearly: leadership is about taking responsibility for what happens next.

I instantly understood what he meant. It was my responsibility to enact change and always had been. I could not stand by, complaining, and wait and hope someone else would solve all the problems I saw so clearly. When I left his room, I did not go back to my office. I thought for a minute, pacing outside the door. What do I do next? What needs to change? Then I went straight to the office of our General Manager, walked in, and told him that I wanted to help get the team back on track. I told him that I saw the problems, felt passionate about fixing them, would take on whatever responsibilities were needed, and I already had the sketch of a plan. I requested to form a cross-discipline team to make the it happen. Somehow, he believed me and put me in charge. What followed over the coming months were the greatest set of leadership experiences I’ve had. They set the foundation for everything that came after in my career and, more importantly, helped revive our team. It all started with that simple advice.


Future leaders,

I believe that we each make our own story in life. The most frustrating thing that can happen is to be caught up, powerless, with no control over the narrative. It’s not only frustrating, it’s wasteful of the most valuable currency we have: our own time. If you’ve found yourself in that position, like I did at my old team, then it is definitely time for a change. But the change can come from new scenery or it can come from within.

Your leadership opportunities aren’t always going to be obvious or pre-packaged, but they are everywhere if you stop and look. Ask yourself, what are the problems your organization faces today? You will reach your full leadership potential the moment you realize that you are one of the rare people who possess the vision for how things ought to be, the competence to know what to do, and the passion to actually make it happen.

Leaders learn to see problems as opportunities. Leaders inspire. Leaders take responsibility for what happens next. Will you?

rock on -nick



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