I’ve spent the overwhelming majority of almost 13 years of blogging about leadership telling people how being a good leader is the most beneficial thing one can to do succeed in business. I stand by that because it’s proven to be true more often than not; yet I can’t deny that sometimes a bad leader also becomes successful.


That seems like a great contradiction; how can someone who’s bad, sometimes horribly bad, end up having good things come their way? Why don’t the people who report to them sabotage them or just up and leave? Why would anyone want to work with a bad leader?

To help illustrate this, let me tell you a story.

Years ago I knew of a guy who was pretty successful in getting people to contract with him to build their websites. I was doing some of the same work on the side, which is how I knew of him. It was a pretty sweet deal he gave everyone; his general rate was about the same as what I was charging, but he’d give them a 50% discount if they signed up with him for hosting their accounts. The monthly rate was higher than what most people would pay for shared hosting but lower than the normal rate for more secured hosting, and he offered a fairly priced management package.

I only met him once in person. He seemed like a very nice guy, well spoken and courteous, and he had an easy manner. Frankly, he seemed like the type of person who’d be hard to get mad at, and it was hard to argue with his success. Because of him, I almost bought my own server to host my own site… luckily I got talked out of it by another friend of mine. Even so, there was something about him that my Spidey senses were warning me about; I always listen to them, even when I’m not sure why they’re going off.

A few people I met talked about him in glowing words… initially. He spent time with them figuring out the basic design they wanted and he’d put the site up on his server. Their sites ran fast and they were happy… until they weren’t.

The problem was threefold.

The first problem was that, though he did “good” work, he did incomplete work. With most websites, you create what you’re initially asked for, then you step away and wait for the client to tell what they think of it, make adjustments until they’re perfectly happy and move on with life. What he did was the first part; after that, he was hard to reach if anyone could reach him.

Why couldn’t they reach him? That was the second problem. He did what a lot of people who built websites did back then, which was to go find more clients. He was very good at that part, which means he was always signing up new clients to boost up his income, and by the time his current clients needed to get back to him all his time was being spent with the new clients.

It might seem that he was just overworked but as someone who did the same kind of work, the hardest part is always in the initial creation; everything after that is really easy. In other words, what he “wasn’t” doing was intentional.


The third problem was having their sites being hosted on his server. There are many small web creation sites today that offer more dedicated hosting, which wasn’t the norm then, but you really need to know someone and trust them immensely before you go there. In this case he had everyone who signed up with him over a barrel. Most of them had no idea how to move their website to another host, and since they couldn’t reach him by phone they felt powerless to do anything about it.

He had a very nice run for about 4 years before things caught up with him. Even then, he already had enough money so that losing the business didn’t affect him much. He left the area and is probably trying to do the same thing to others in another community.

This story doesn’t touch upon all the issues that allow bad leaders to be successful, but it touches upon a lot of the themes. Let’s take them in order:

1. Bad leaders can be really engaging. They can lull you into a false sense of security and make you think they’re at the top of their game. Even if they don’t come across as being all that nice, they can come across as someone confident and successful, qualities a lot of people are drawn to.

2. Bad leaders are usually really good at something. It’s possible that they’re the best at the work they do but it’s not always necessary. Some are great at selling a promise. Some are great at making their competition seem weak and inferior. Some are psychopathic liars; those are the best liars.

3. Bad leaders sell promises without worrying about the consequences. There’s often no long term strategy, only the here and now. They find something they’re good at that they can get others to fall for, then they keep doing it to the next person, the person after that, and so on. If we were talking finances we’d be talking Ponzi schemes. All they need is one small success to build on and it’s an upward climb from there.

4. Bad leaders never accept blame for anything. Even if you catch them red-handed, they’re going to deny and deflect any bad behavior or performance complaints against them and find ways to blame others, including you. Because they’re such adept liars, they can get a majority of people to believe them or forgive them… which is strange since there’s nothing to forgive them for since they didn’t ask for it.

5. Bad leaders are pervasive. Unfortunately, most people are used to dealing with bad leaders, so when they see another leader exhibiting bad behavior it feels more like the norm than something that needs to be taken care of or to stay away from. If you’ve ever wondered why so many seemingly intelligent people fall for scams, this is the reason why moreso than being greedy.

With that said, most bad leaders will have something bad happen to them at some point. Those who aren’t set up to ride out the storm will end up in the most trouble (think about Travis Kalanick of Uber, who had to give up participation in his own company, although he still left rich), possibly never to recover. Those who can either learn from their downfall (like Steve Jobs) or have the chutzpah to persevere (Don Imus) will either hang around or, somehow, go to even greater heights.

Life isn’t always fair. Still, I believe in this quote of Albus Dumbledore of Harry Potter fame: “It is our choices that show what we truly are, far more than our abilities.” Which choice would you rather make?
 

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