This will be long. Bear with me, please…
I used to have the worst boss. For real. I would put this guy up against anyone else’s “worst boss” and I think I might still win. No, your crappy 19-year-old boss at the 7-11 or Wendy’s doesn’t count. This guy was a VP at a Fortune 100 company. Someone you’d think might be qualified in some way to lead people. He wasn’t.
Some Background
The boss was the VP of IT at a major retailer. I won’t name him or the retailer, but if you know me you already know who I’m talking about. (We’ll call him Paul for ease of reference.) I was the Director of Application and Database development (a mouthful). Basically, I was the #2 guy in IT at the company.
I was put in place because Paul was failing. The CFO forced Paul to hire me over his objections. Paul wanted to hire a crony of his. I didn’t apply for this job or seek it out. I got a phone call one day that said the CFO wanted to speak to me. He handed me a piece of paper, which was a job offer, and, in a moment of temporary insanity, I took it.
I knew going in that Paul sucked. I had worked with him in the past. I thought I knew what I was getting into. I looked forward to the challenge.
I was wrong. The guy was somehow worse than I expected.
The Signs
I could easily fill a book about my experience working for Paul, so I’m trying to keep to just the relevant points. There is an ultimate point here, I promise.
The first sign I had that Paul was worse than I expected was when he publicly threw one of his subordinates under the proverbial bus. In a meeting with all of the highest leaders in the corporation, Paul was asked about a project that was not going well. He took no responsibility. Instead, he blamed one of his subordinates, and said that this guy was lying to him about his progress and not cutting it in his job.
That wasn’t true. In reality, Paul hadn’t ever handed the project off to his subordinate. But Paul was very comfortable slandering this guy and basically neutering his reputation to save his own ass.
The next big sign came during a crisis. One day email just stopped working. No one had email anymore. Obviously a complete lack of email is a major issue.
In a situation like this a leader would gather people together, get all the key players in the room, and make a game plan to figure out a solution. Paul gathered up all of his personal effects, put them in his backpack, and declared to someone who was passing by his office that he was quitting.
That left a very confused group of people, and no leader. We found Paul a few hours later wandering around the 7th floor. He was going from PC to PC seeing if he could get the email to work. He hadn’t quit. He just had a breakdown of some sort. When he came back he never addressed the packing up of the personal effects, or the disappearance. He acted like nothing had happened.
The Confrontation
The email incident prompted a quite heated (and somewhat surreal) confrontation between Paul and me. Words were exchanged.
I told him he needed to decide if he was going to work here or not. If he was going to quit, fine. If not, then he needed to get his head in the game and start acting like a leader. His team needed leadership, something which he was not providing.
He responded in a bizarre way. First he told me that “he had always been a high achiever,” and went on about how he had always had good review scores, and how he always succeeded at whatever he tried. He used the phrase “high achiever” many times during this speech.
Then he said something that surprised me. He told me that he “could do the jobs of anyone on his team better than they could do their jobs themselves.” He then went on to name several positions, including mine, and note how he could do that job better than the person who held it.
Really?
This claim was shocking to me because it was so much the opposite of my philosophy of leadership. I always sought out the best and brightest people for my teams. I was proud of the fact that I couldn’t do their jobs better than they could. If I could, why did I need them?
I built teams of people who didn’t agree with me. We’d argue, debate, and in the end I’d make a decision, knowing that my decision was informed by a diverse group of opinion. It was their job to bring their best, and my job to take all of the varying opinions into account and make a decision based on my view of the situation.
Paul’s view was different. He thought he was the best and the brightest, all in one. He also thought of himself as a “high achiever.” He wasn’t. Maybe he was in the past, but he was obviously now in a position that was over his head. He didn’t have the skills or ability to succeed in a high level job like a VP. He was a failure.
He was “downsized” a few months after the email incident.
The Point
So I was reading an article the other day, and this jumped out at me:
Obama, who is not without an ego, regarded himself as just as gifted as his top strategists in the art and practice of politics. Patrick Gaspard, the campaign’s political director, said that when, in early 2007, he interviewed for a job with Obama and Plouffe, Obama said that he liked being surrounded by people who expressed strong opinions, but he also said, “I think that I’m a better speechwriter than my speechwriters. I know more about policies on any particular issue than my policy directors. And I’ll tell you right now that I’m gonna think I’m a better political director than my political director.”
Reading that did not surprise me. In fact, it made things quite a bit clearer.
Barack Obama, like Paul, thinks of himself as a “high achiever.” He thinks he is a better speechwriter than his speechwriters, more knowledgeable about policy than his policy directors, and on and on.
Perhaps Obama was once a “high achiever,” I mean, he did get elected President after being in the Senate for like 10 minutes. But, like Paul, he’s now in way over his head. And like Paul he got there by throwing the little people under the bus.
The Epilogue
The fact that Obama considers himself the smartest person in the room gives you perspective on his decisions.
No wonder he rejected all of his general’s plans in Afghanistan. After all, Obama is a better general than his generals.
Barack Obama is a “high achiever” in the mold of Paul, the worst boss I’ve ever had. I just wish we had the ability to downsize him before the damage he does becomes irreversible.

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