I have worked for a number of people. You should look at my LinkedIn. My friend Angela calls it a sad procession of career one-night stands. I wonder if she meant it as a compliment. No matter where I have went, every one I have worked for and with have all been great people. Personally. Based on my interactions with them, I can say that they were universally kind, thoughtful, and caring for their fellow person. They might be basement serial killers in their free time but in that case I would be the first guy on CNN shaking my head and saying, “Would have been the last person I imagined.” Great people, personally.

That being said, they were not all perfect professionally.

I was taking a walk and had started getting to think about that age-old generic concept of leadership. Caution: There are certainly plenty of Harvard Business articles and case studies that you can read in where you can take on and learn about the frameworks of leadership. Stuff written by people with a whole lot of experience and cool PhDs. So if you want stuff backed by research there are some great resources.

After thinking a bit about the things I liked most about the leaders I liked following and some things I did not like about those same people and managed to center on three traits. They are communication, focus and pragmatism.

Communication

To me in literal terms, someone who has good communication skills is someone who can capably transmit information from their head to yours. It is tougher than you might at first think. You might have an abstract and not so clear concept in your head of what you want to talk about or what you want people to do for you. You might just have a basic goal and a view of what the end should be but not really a clear picture of what the steps of accomplishing this.

That is fine if this is the case. There have been plenty of times where I hear a vague end point and can do a decent job of figuring out how to get there. However I would not be pleased if what I hear is not what they want because they did a poor job of communicating to me the end goals.

I think people are mostly aware of this when they are talking to you in person. Many people would tell you what they want and then tell you again and again. It is helpful for them too because they are doing their best to solidify the concept in their head. Because I am there in person, I can help them get there too with good questions about what they are looking for. That is part of my role as a listener, just trying to get a sense of what they want.

Oh, and you do not have to be a great speaker - like Steve Jobs level salesman or Bill Clinton level speech giver - in order to be a good communicator. It is more important to be considerate of your listener and be emphathetic of what their perspective. I know one person who is a great communicator of ideas and complex concepts and she is not a great speaker. She gives crappy presentations and does not really have a loud voice. What she does have though is a really sympathetic view on her listeners. She recognizes what the audience might not understand. In my view, that is probably because she also trips up on those exact points. When she gets to something she is not 100% clear on, she makes sure to check up and follow up. “Did you get that?” “Did that make sense?” “When I was learning this, I had issues with this and that. Such and such. So how about you?” I really enjoyed working with her because there were no surprises. She felt like she was ahead of me and knew what she wanted, and when someone knows what they want then their followers can meet their expectations.

Bad communicators are people who do not understand what they are saying and that there can be a misalignment between what they think in their head and what is coming out of their mouth (or onto the screen in words). They think potato and I hear tomato. I ask them what they might mean by that. They tell me something almost completely different from the first thing. Wait, what? I get confused. Did they get better/worse at communicating what they thought or did they think something completely different? You can tell that suddenly there is a number of factors introduced that end up kind of confusing and muddling up the process. I do not want to spend time working at something they might not want so I keep asking them and every time I get a different answer. What is it going to be? They get frustrated and I get frustrated.

The ways to solve communicative skills is practice. You spend a lot of time explaining things to people. I try to do that. I am not a good natural communicator. I have pronounciation issues with words. I am more comfortable communicating with people behind the keyboard than in person at least with respect to the goal of getting the idea across to them (it is still nice to speak to people in person because you want that human interaction). One of the good things about practicing communication skills is that you tend to do that when you are having stronger and more meaningful conversations with people. You do not need great communication skills if you are discussing the Niners’ win over the Packers. You do need them when you are talking about whether or not people really have soulmates and why.

(I want to touch briefly on email and writing before moving on. There are a multitude of attitudes to email. Some people treat it like a conversation piece, almost like Instant Message. You cannot construe the thoughts from these people as “canon” or what they are looking for. It is just like a transcript of a conversation in person. You just have to realize that they are trying to flesh out what they want. There are other people who when they write something out, they write big long treatises with questions. Whichever style that a person is, that is fine. For myself it is important that I figure out which type person I am working with.)

Focus

I remember working with a boss who we joked had a sort of “wheel of priorities”. Kind of like the one that your parents watch on television at 7:30 PM after Jeopardy. Every day when we got in for work, our boss would review his email and it seemed like whatever was the latest crisis (and if you are working in a startup then you would know that living the startup life is a rolling pearl string of crises) and then automatically assign it as the “Top Priority”.

Someone on a sales call mentions that they would like to see the product have some multi-lingual capabilities? No worries, Mrs. Customer this is now the TOP Priority at our little startup.

Someone in Baghdad writes to us asking for an international rollout to Iraq? Well, golly this is now our number one goal!

You are showing someone a beta product and the front page JavaScript freezes? Then geez let’s make a sprint and get all of these bugs fixed! (This sentence ignores the actual definition of “sprint” as well as assumes that the number of bugs is finite.)

I am getting little emotional here. Let me calm down for a second.

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Okay I think I am good.

I think one of the most important things to have not only as a manager but as a person in general is focus. By that I which mean to say the capability to really hone down and ignore the things that do not matter. It means having the capability to clear out everything that is buzzing around your ears at the moment and giving your all on the things that matter.

“Things that matter”? It could something concrete like the work sitting on your email right now that needs to get done right now. But it could also mean something abstract like being able to focus on what matters in getting the long term goals achieved. The world is a confusing, discombobulating place and there is always easy to get lost in the mix. Being able to recognize that there are some things that do no matter to our long term goals is vital. Just like being able to recognize that there are some people in your life that do not matter (but this is a post for another time). Being able to wave your pimp hand and say, “Yeah we don’t care about that”. Yes I can call that focus too.

Pragmatism

If someone from high school were to ask me about the one attitude to have about life, I would tell them to not give a shit about other people. Unfortunately this is America and parents are not comfortable with having euphemisms of excrement being slung into their kiddies’ ears.

Thus I would button up my shirt, polish my leather shoes and then tell them the more PC thing to say. I think one could benefit a whole lot from being a “pragmatic” person. What does that mean? It means being able to look realistically at a situation - including your own - and making a reasoned, rational, and often compromised decision with the goal of getting the most utilitarian benefit from it.

There are two historical figures in the past 200 years I really admire. They are Deng Xiaoping and Abraham Lincoln. They are quite different people. Deng is about 5 feet tall. Abraham is 6’4”. Deng is Chinese. Abraham is not. They never met each other. They are both kind of weird. Deng got to live until he was in his 90s. Abraham never made it to his 60s. Yet at the same time, there is a lot that you can say about the two men that overlaps and applies to both. Both men united their countries from deep schisms. Both men are incredibly smart political operators. But most importantly for myself, they are very pragmatic and practical men. They both did horrible things. Abe Lincoln violated Constitution by suspending of habeas corpus. Deng Xiaoping allowed the Tiananmen Square slaughter in 1989 to happen. These are both crackdown on individual freedoms. Yet at the same time, the good that they did in the long run was much greater. They spent in order to receive, and while there is admiration in the persistent soul drawing the red line in the sand and clinging to the moral high ground, the real world is 50% gray and the admirable person is able to know when to forsake what is most precious to them.

I admire the clonking of their big gigantic balls of steel to do that.

Conclusion

Huh. That last one I did not give a single concrete example of a manager who actually did that. What a terribly written paragraph, you would think. However, it is for a reason. The first two came pretty easy to me. I had a lot of examples in mind. Pragmatism, though, was tougher. I thought and wracked my brains for so long but nothing came to mind. I was not sure whether I had the long term vision to recognize it when I saw it living, breathing in person in front of me. Pragmatism, the way I wrote about it in the section above, seemed to only exist in the pages of Wikipedia centuries after the fact. Not in an office that thinks about the next month’s sales.

It is unfortunate of me and says a lot about my own flaws as a potential leader. Every year I try to think about what I need to work on and improve as a worker and human being. Perhaps this is something I need to focus on this coming year.