I've had a couple of conversations recently about what it means to be a good leader in business. It's an important topic for me, because while I've flirted with entrepreneurship, ultimately I don't know if I could commit to it because I'm uncomfortable with the idea of being on the hook for other peoples' livelihood (read: their paychecks). So I'm kind of resigned to working for others, and I've made some pretty horrible choices during the wandering phase of my career. Over time I feel like I've collected a fair amount of data about what to look for. I should probably write a book about it at some point, from a software development angle, of course.
Maybe we need to define what it means to be a successful leader. The truth is, we all know about CEO's that failed and generally sucked, and there are a great many leaders in small to medium-sized business that keep getting paid for years even though they clearly aren't good at what they do. Success isn't really measured by the ability to get paid or stay in business. To me, it's measured by the quality of your product, your people, your longevity and your outcomes.
The first and most important quality among leaders is not unique to business leadership. In those roles as in life, you absolutely must be self-aware. If you can't approach everything with the humility of knowing what your weaknesses are, I don't think you can be truly successful. This is hard for me, maybe because of my undiagnosed ASD tendencies (other people just seem so wrong all of the time!), but that I can admit it might itself mean I'm self-aware.
I used to think that Type A personalities were better suited to business leadership than Type B, but I've met a number of people that have completely squished that theory. One CEO in particular that I've learned a lot from, without even working for him, is definitely more B. I do think Type A's are more driven to leadership, but I don't think they're better leaders for it.
Self-awareness plays a big role in knowing personal limitations, and how and when to collaborate. The best leaders have vision, set direction and hold people accountable, but they mostly delegate. They're leaders that guide, not direct. That admirable CEO replaced one that wanted to get hands on everything, and as the company grew, he became less effective in his micromanagement. Of course, he wasn't self-aware of this. Mid-level managers are the worst about this, because they can't timebox work, and expect everyone else to disregard time in the same way, making everyone miserable. Knowing where you stop and others start begins with hiring really smart people and letting them run with things that they're better at.
I think too much is made of the difference between leaders who are visionaries and those who are operators. Both types, think Steve Jobs vs. Tim Cook, can be successful if they lead with self-awareness around their limitations. I think Jobs was mischaracterized as being a control freak, but was he? His vision was extraordinary, but he needed a Cook to understand supply chain to make the vision happen. Conversely, Cook isn't the visionary, but Johnny Ive and his inner circle can be.
The one additional quality that I think defines success is to see what isn't there. That's probably the rarest of qualities. How do you know what's missing if you can't see it? Is there a market that you're missing, or a pivot you can make that will redirect you toward success? Humans are creatures of habit, so I give anyone a pass who can't do this. It's certainly one of my shortcomings, and you might have already guessed that I overcome it by giving others the opportunity to see what I can't.
If the various books I've read on leadership fail at anything, it's that they never talk about the self-awareness and humility. These qualities are often associated with a lack of confidence or weakness, and that's a load of crap. The thing that always gives me confidence, and confidence in those I work with, is the ability to challenge each other in a respectful way. I get it every day both with my boss and the people who report to me. I'm not saying ego is always a non-factor, but most of the time we reach conclusions that get us moving in the right direction.