“Nice guys finish last.” ~Leo Durocher

"Winners have simply formed the habit of doing things losers don't like to do." ~Albert Gray

Does winning trump everything? Including some of the basic tenets of leadership, like collaboration, respect, and thinking long-term? It’s a fair question, as history is riddled with people who accomplished amazing things and are revered and respected for those things, but were complete jerks.

But why is it that being “bad” can be such a successful technique for these people? And what can leaders learn from it to gain the benefits, without being a jerk about it? Turns out that a jerk's nature has some positive traits, even if they aren’t applied in a particularly “nice” way:

Demand excellence – Probably the best illustration of a good trait gone bad. Any great leader demands excellence from their team, but they get to excellence by nurturing it, investing their time into it, and becoming partners in it. It’s a time consuming and effort intensive process that doesn’t always get to where you want it to right away, which is why many good leaders struggle with it.

A jerk may achieve that excellence from their employees, but they focus on getting it right now! To heck with the long term consequences. They simply demand excellence and use fear as the primary weapon to obtain it. This fear can come in the form of threats, uncomfortable angry outbursts, and eventually simply the implication that either could occur if you fail. They give little mind to the consequences of getting there; what procedures need to be broken, what overtime needs to be worked, or what other projects need to get pushed aside. The result may be excellent output, but with an undermining of the foundation of the organization.

Confidence – Confidence is a requirement of great leadership. You must be self-assured in your ideas and plans to be able to see them put into place and brought to fruition. It also takes confidence to be a part of the feedback loop by being willing to give your opinion.

Jerks are plenty confident, but it manifests itself in being a bully. They are assertive in the extreme and almost always give their opinions on things, which can seem to the uninformed as if they have a lot of ideas. And in many cases they will consider their own ideas to all be “great” and will use this assertiveness and confidence to mask otherwise poor results in a veneer of excellence. Have you ever been in a room with someone who brags about results that aren’t that “brag-worthy?" That’s what a jerk does with their results. Constantly.

Risk tolerance – Leaders quickly realize that almost anything worthwhile that they want to do will require some risk. The calculation and minimizing of that risk is a process that must be balanced against taking action. Many times leaders will be too risk averse or not take action quick enough, and sell their potential short.

Jerks have no problem taking risks. Yes, they are confident, but also because they have a ready response if the risk blows up in their face: Blame and Excuses (usually both, just for good measure). They will throw their team or another department under the bus as quickly as possible and project the knowledge gained from hindsight to back that up. This practice often makes their leadership far too risky and they jeopardize much more of the organization.

Competitive and ambitious – Competition helps to focus our efforts and win as a team. Ambition is a cousin of competition and helps us to raise our goals and to become our best selves. What people realize as they keep making steps up the career ladder is that their individual achievement relies increasingly on getting the best out of others. Many times leaders will not stoke the fires of competition and ambition out of this selflessness.

Jerks never look too much past themselves. Their work is self-serving and self-obsessed. They are unbelievably competitive and ambitious, but they don’t play fair and they don’t play nice. This might work for a while, but this is also why many stall at certain points on the career ladder as their predisposition to themselves inhibits their progress. Yes, there are plenty of jerks who through intelligence and/or scheming rise higher, but their inability to serve their team and others almost always comes out.

Stubborn and pushy – All leaders need to fight for their ideas and beliefs. Resource constraints in almost all organization require that some ideas get left behind while others are pursued. The thing is, great ideas don’t always look that great when they are first put on paper. It takes a leader with some stubbornness to fight for their idea and see that it gets played out.

Jerks tend to win this game simply through numbers. They may not have as many great ideas as their peers, but MORE of their ideas get pursued because of their dogged determination and disregard for the value of other people’s ideas. If you’re allowed to throw enough darts at the board, you’re bound to get a bullseye eventually. And these people always make sure they get as many chances as they possibly can.

Focus on strengths – Yes, you need to address your weaknesses so that they do not hinder your progress any more than necessary. But great leaders play to their strengths so that they can accomplish as much as possible. They acknowledge weakness so as to address it, but they rely on their strengths to get them through.

Jerks disregard their weaknesses and make every attempt to set the rules so that only their strengths will come into play. If it is a weakness, they simply shift the responsibility for that area to their team or to another department. And using all of their “tools” above, they often are able to. This leaves them with no weaknesses, only strengths, which helps them to exert their influence in the areas those strengths touch.

Great negotiators – Negotiating and compromising are always difficult in an organization. The complexities lie in the fact that almost no negotiation is a one time event. There will likely be more down the road, and you'll likely be working with the person continually. You must always try to strike that balance between you and your counterpart so that the long term needs are satisfied and you both walk away happy (or at least with an understanding).

Jerks look at each negotiation as its own instance with no regard for future relationships. They will serve their needs at the cost of the general good, which if their boss doesn’t have a wide enough vision of the organization will look like they obtained a victory. This is often the case, especially considering that their counterpart on the other side of the negotiation isn’t typically interested in discussing how they got the bad side of the deal.

The reason that jerks can be so successful is that they misuse these traits for self-serving and short-term gains. In most organizations their leaders are detached enough from the operation to where they will never see that downside, they only see the "success." And by the time they do see it, the jerk has positioned themselves as a person the boss can trust and they talk their way out of it.

While there isn't much you can do about any of that, what you can do is begin applying these traits in your own leadership in the way they were meant to be applied. If you're successful you'll find that your career trajectory will likely be higher than any of the jerks in your organization.