A number of years ago, I spent several weeks in Costa Rica on a mission trip with some people from my church. From what I can gather, there are insufficient funds in Costa Rica to keep the roads in good repair–at least in the area where we were. 

Additionally, Costa Rica gets lots of rain, which results in huge potholes in the roads.

If you drove into one, you might seriously damage your vehicle and perhaps hurt yourself. The solution they came up with was to put oil drums in some, but not all, of the holes (I am not kidding). That made for interesting driving. You basically drove in such a way so as to avoid the oil drums and on whatever side of the road was necessary to keep from hitting one. It was especially interesting at night. Being in a few taxis in Costa Rica deepened my prayer life.

Leadership can be like driving on the Costa Rican roads; there are derailers(potholes) along the road that need to be avoided or you will be in big trouble.

In my experience from being in vocational Christian ministry for 53 years, here are four derailleurs that I have seen.


The demands on leaders are horrific. So many expectations, so many people with significant needs and issues, and so many urgent and demanding decisions that scream for one’s attention and energy. Put all this together with the fact that many leaders are doers and accomplishers by nature and the result is precious little time taken for reflection…reflecting on my own life, reflecting on where I’m headed, and reflecting on what the most important things are on which I need to be focused in any given hour, day or week.

We become reactive (putting out fires) instead of being proactive (lighting fires). Solitude, time to think, to pray, to catch our breath is so critical to longevity in leadership. It was Socrates who said, “The unexamined life is not worth living.”I’m not sure I would go that far, but certainly the unreflective (unexamined) life has the potential of derailing you big time!


Unawareness can take different forms, but I’m thinking here of being unaware of the needs of people closest to me…those in my family, my direct reports, and those on my leadership team. When I am super busy and moving at an insane pace, I stop asking questions, stop listening, stop knowing about the needs of those around me. I can become tuned out. Meetings are all goal-focused and I’m not aware of what’s going on with the people I’m leading. Am I truly aware of how they are doing? Am I aware of how their family is doing?  I can ask transactional questions which are superficial and routine and keep me in the dark about what is really going on.

Leadership can become all about getting to the goal, getting things done, checking things off my list. My experience has taught me that the faster I travel, the worse I become at paying attention to and listening well to the important people in my life.


I can be aware from a factual point of view, but still be unsympathetic. Awareness is the first step, but it needs to move to God-enabled compassion and sympathy. Due to being a goal-oriented bottom line thinker, this is my biggest challenge.

There is an old saying that sounds like an empty cliché but is nonetheless very true: People don’t care about how much you know, but they want to know about how much you care.

Hurting, beat-up, abused, misunderstood, frustrated and exhausted people want to know that you really care…that you are really interested in them…that they matter to you personally and to the calling and vision you have received from Jesus.

Can I trust you? Am I safe with you? Do you really care about me? These are all questions followers have a right to ask of their leaders. The leader who is all wrapped up in himself not only makes a small package, but will also drive people away, have them move on because of your perceived hypocrisy and narcissism as it relates to loving them. People leave a leader, not a job. And the leader they will most likely leave is an unsympathetic one; a leader who doesn’t genuinely love and care about people.


Leadership can be lonely and, oftentimes, is. If you have been burned a few times, you begin to not trust people or share your emotions, fears and issues with others. You start to withdraw, disconnect or play your cards close to the vest (to use a gambling metaphor).

You start to spend more and more time by yourself…tend to not have close friends…stop getting adequate feedback prior to important decisions. You can slowly become disconnected from reality and think you are always right. You can even become paranoid, thinking someone is out to get you or to betray you. This is a derailer for many leaders.

Leader! How are you doing? Are you close to hitting an oil drum or falling into a pothole with no oil drum? What would Jesus have you do in trusting Him and cooperating with Him in making some changes?