Leaders Encounter Obstacles

As leaders we face real obstacles and recognize that each one contains within it opportunity and risk.   Identifying options before action are important in becoming an exemplary leader.   In the article, we have outlined 8 options.  What did we miss?

1) Wait for it to move

It could be that what is truly blocking us is about to move itself out of our way. In times like these we must exercise patience, keep learning, keep growing, and keep adding value to people.  How long do we wait will be the test.

2) Move it yourself

In some instances, we can move the obstacle ourselves.  This is the easy way, but is not always the best.   Be careful as the weight of the blocker may not be known and we can hurt ourselves or others if we move it. In addition, when we do this alone we may lose the opportunity to coach others through it.

3) Ask for help to move it

This is a good choice when others are around. It also depends who those are that hear our call. It may be those that come may make our condition worse. We should be careful who’s number we have on speed dial.

4) Go around it

This can work, but how do we know which way to take; right or left?   We each have a few of these to make in our lives and typically we don’t have the option to go back and choose again.  Going around can take a long time; we should be sure we are ready for the journey.

Over, Under, and Through

5) Climb over it
This one makes sense if we are prepared for a climb and if we have some idea that we can get back down on the other side.  We recognize that while we are climbing we have little defense and remain vulnerable each step we take. However, this is the best approach to overcome some obstacles.

6) Go under it
This option carries other unique risks as we could be crushed should our efforts cave in on us while under the obstacle. If it works, it may be the shortest path to the other side, but we may not find ourselves the same person when we come out of the dark and have dug in the dirt for such a long time.

7) Go through it
This takes brute force and the right tooling and could be the right path.  We need to count the cost of this option.  Going through an obstacle could be the last decision we make because we may not be able to finish what we start due to the pain.    Admittedly, people we admire most take these types of risks and their names are remembered in history because they give everything to overcome the obstacle before them by tackling the problem head on.  Sometimes they succeed; sometimes they don’t. Either way the obstacle takes extracts its price.

8) Turn around

Is it possible that we recently jumped on the wrong path and the obstacle we have encountered we should never have seen?  If we go no further and turn around we might yet find the path we were supposed to take in the first place.


When we think about how best to help our teams when they encounter an obstacle, there are many options to consider and our role is to help them identify the paths open to them. After that, it is up to them to draw their own map.

Shepherding: The art of becoming the leader others want to follow

4 Replies to “Leaders Encounter Obstacles”

  1. A variant of #3 is to ask someone who has encountered the same obstacle and potentially learn from their experience.

    1. Thank you Steve. This makes perfect sense. As I think of how you mentored me over the years, I definitely used this approach frequently.


  2. Sometimes, when turning around, the obstacle is something that makes the destination unreachable. There are decisions to make. Sometimes, the destination can be adjusted. Other times, the journey just needs to be abandoned.

    1. Important points Jack. I have experienced times where I have needed to abandon a desired destination. When that has to happen I’ve found pain comes with it.


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