Observations on leadership

posted by Jeff | Friday, April 10, 2020, 10:30 PM | comments: 0

One of my former coworkers from more than a decade ago recently posted a tribute of sorts to our chief architect at that job. He helped to cultivate a culture that is extremely rare in software development, where there was a shared desire for continuous improvement, close collaboration and engagement with the business and just doing the best work we could. More than a decade after that company imploded, I've never been a part of anything quite like it.

Of course, the other side of that is that the non-technical leadership made some serious errors that led to the death of the company, which is pretty frustrating because it was a bona fide business model that should have endured. It's one of the first times in my career that I experienced a huge reversal in respect for the leadership. I've seen that disappointment a number of times since, and it weighs heavy on me to never be "that guy" in the roles that I've since accepted.

Countless books have been written about effective leadership, both from third-party perspectives and those that are largely autobiographical. It's really hard to distill what makes effective leaders down to a few things, and I tend to take little bits and pieces from each of those that I admire.

In politics, I find that leadership measurement doesn't fit the conventional definitions either. While my political alignment is all over the place to an extent, it doesn't align well with party. For example, I think Bernie Sanders' call for universal healthcare is absolutely the moral and correct outcome that we should pursue. But he's a terrible leader and an inflexible ideologue that would never be able to bridge the gap with those who disagree with him. You can't do so when you're declaring war on a segment of the population that is not itself the problem as much as it is the system. Conversely, I would categorize Governor Mike DeWine of Ohio to have some of the worst policy positions in the history of the state (especially on reproductive health rights), but he's currently demonstrating in a crisis how to lead by listening to experts around him. And don't even get me started about a leader that thinks the ratings for his press conferences are a measure of success.

My own playbook is pretty small. First, surround yourself with people that are smarter than you and compliment you with experience that you don't have. Second, enable those people to create your desired outcomes, and hold them accountable to those outcomes. Third, respect, value and appreciate the people who accept that accountability, without coddling them. And finally, accept that you have blind spots, and don't reject the reality of those just because they make you uncomfortable.

Leading is hard. I'm sure some people have a natural instinct to do it, but it's not easy. I often wonder, what percentage can I get right? Am I failing when some people can't come along, or is it on them? Am I better at it than I was a year ago?

Back in my volleyball coaching days, I learned a very important lesson, and it informs my view on human nature. If you can trust a group of people to take what you've given them, and encourage them to take ownership in it, most of the time, they will deliver for you. I had a series of teams, teenage girls, where I gave them a framework for success. They weren't the tallest or most talented kids, but I gave them a system to own, and they really, really did well with it. Sure, I did have one group that wasn't having it, and it took me a long time to realize that it wasn't my fault. You can lead a horse to water, as they say. But most of the time, leadership works when you empower and get out of the way.


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