In 2004, Sydney Finkelstein of Dartmouth College published an article entitled “Why Smart Executives Fail.” Eric Jackson from Forbes revisited the seven habits of spectacularly unsuccessful executives in a recent article. Here are those bad habits, followed by some personal observations.
Seven Reasons Smart Leaders Fail
1. They see themselves and their companies as dominating their environment. They vastly overestimate the extent to which they actually control events and vastly underestimate the role of chance and circumstance in their success. CEOs who fall prey to this belief suffer from the illusion of personal pre-eminence: Like certain film directors, they see themselves as the auteurs of their companies. As far as they’re concerned, everyone else in the company is there to execute their personal vision for the company.
2. They identify so completely with the company that there is no clear boundary between their personal interests and their corporation’s interests. CEOs who possess this outlook often use their companies to carry out personal ambitions. The most slippery slope of all for these executives is their tendency to use corporate funds for personal reasons. . Being the CEO of a sizable corporation today is probably the closest thing to being king of your own country, and that’s a dangerous title to assume.
3. They think they have all the answers. Leaders who are invariably crisp and decisive tend to settle issues so quickly they have no opportunity to grasp the ramifications. Worse, because these leaders need to feel they have all the answers, they aren’t open to learning new ones. Leaders who need to have all the answers shut out other points of view.
4. They ruthlessly eliminate anyone who isn’t completely behind them. CEOs who think their job is to instill belief in their vision also think that it is their job to get everyone to buy into it. Anyone who doesn’t rally to the cause is undermining the vision. The problem with this approach is that it’s both unnecessary and destructive. CEOs don’t need to have everyone unanimously endorse their vision to have it carried out successfully. In fact, by eliminating all dissenting and contrasting viewpoints, destructive CEOs cut themselves off from their best chance of seeing and correcting problems as they arise.
5. They are consummate spokespersons, obsessed with the company image. Instead of actually accomplishing things, they often settle for the appearance of accomplishing things. When CEOs are obsessed with their image, they have little time for operational details. As a final negative twist, when CEOs make the company’s image their top priority, they run the risk of using financial-reporting practices to promote that image. Instead of treating their financial accounts as a control tool, they treat them as a public-relations tool.
6. They underestimate obstacles. Part of the allure of being a CEO is the opportunity to espouse a vision. Yet, when CEOs become so enamored of their vision, they often overlook or underestimate the difficulty of actually getting there. And when it turns out that the obstacles they casually waved aside are more troublesome than they anticipated, these CEO have a habit of plunging full-steam into the abyss.
7. They stubbornly rely on what worked for them in the past. Many CEOs on their way to becoming spectacularly unsuccessful accelerate their company’s decline by reverting to what they regard as tried-and-true methods. In their desire to make the most of what they regard as their core strengths, they cling to a static business model. They insist on providing a product to a market that no longer exists, or they fail to consider innovations in areas other than those that made the company successful in the past. Instead of considering a range of options that fit new circumstances, they use their own careers as the only point of reference and do the things that made them successful in the past. The problem is that after people have had the experience of that defining moment, if they become the CEO of a large company, they allow their defining moment to define the company as well – no matter how unrealistic it has become.
I want to revisit this list and add some of my own thoughts geared specifically to church leaders. My comments are part personal reflection and part warning.
Seven Reasons Smart Church Leaders Fail
1. Finkleston says unsuccessful leaders see themselves and their companies as dominating their environment. From someone who once preached a sermon series called “Dominate,” I can relate to this warning. With rose colored glasses, I looked at what we were doing as unique, amazing and unlike any other church in town. My belief that churches of all styles and traditions were valuable was not backed up in my actions. I had a chip on my shoulder, and it wasn’t pretty.
2. Finkleston says unsuccessful leaders identify so completely with the company that there is no clear boundary between their personal interests and their corporation’s interests. Starting a church was more than my job – it was my hobby and my obsession. Focusing on leading at a high level led me to insulate myself from people who couldn’t help me to get to the next level. I didn’t have hobbies. I didn’t have friends. I was the church. And the church had my personality. In retrospect, healthy separation would have been a good thing. Hobbies, friendships and energy spent outside of the church would have been good for me.
3. Finkleston says unsuccessful leaders think they have all the answers. Confidence quickly becomes cockiness, especially in church leadership. This is something I struggle with constantly, and stubbornness usually isn’t helpful. Yes, there are times when you must lead with commitment and make executive decisions, but refusing to learn from other viewpoints is not a commitment to vision, it’s a character flaw. For me, I ran with a tribe of leaders who did ministry the same way – though I realized that the Kingdom was bigger than me, my world was small.
4. Finkleston says unsuccessful leaders ruthlessly eliminate anyone who isn’t completely behind them. Vision is super important in any church – young or old, but vision can become an idol. It can cause us to shut people out who don’t share our opinions or only associate with people of similar preferences. Please don’t misunderstand – clarifying and communicating a vision is important, but policing who is in and who is out should not be an obsession.
5. Finkleston says unsuccessful leaders are consummate spokespersons, obsessed with the company image. Obsessing over image sounds a lot like focusing on the form but ignoring the substance. We all know brand perception and name recognition is important, but what we look like is not more important than what we stand for. Instead of working on your image and reputation, perhaps we would be better off building substance. In my personal life and ministry, I was overly concerned with my followers and fans. Social media became a device to carefully manage my (and the church’s) image.
6. Finkleston says unsuccessful leaders underestimate obstacles. People that lead with vision are often so disconnected from the operational details that they lose touch with how things really work. No matter how vision and goal oriented you are, if you don’t have the pulse of what it takes to make that vision happen, you aren’t going to lead well. We emulate the platform and schedule other leaders have, so we try to go there before it’s necessary and before we’re ready. As a leader, you must do more than steward the vision.
7. Finkleston says unsuccessful leaders stubbornly rely on what worked for them in the past. I love defining moments, but trying to recreate them can be deadly. And before we start criticizing the traditional churches with pews and stained glass, stop to realize that you’re probably just as committed to your traditions. When you have to repurpose or reimagine something you initially created, you’ll understand just how hard this is.

After a dozen years as a student pastor, and five years a church-starter, I'm the Chief Operating Officer of 




Great post! The 2nd point was particularly challenging. What starts as commitment becomes obsession… Ouch.