When We Struggle: Understanding Obstacles to Success

It was a simple task. I had an errand to complete for a project and I kept putting it off. Day after day went by and I kept doing everything but this one simple thing—until another team member asked me about it, and I had to confess that it was still unfinished. I was frustrated with myself. How could I let something slip that I had said I would complete?

All leaders have a story like this. We find ourselves hitting an obstacle and aren’t sure why it’s happening. Most of us think a little more grit and harder work is all we need.  But when we are confronted by an unusual obstacle it is worth pausing to consider the source.

Proverbs 20:5 says, “The purposes of the heart are deep waters, but a man of understanding will draw it out.”

Here’s a simple model you can use when trying to draw out your own motives, as well as others that you lead, and identify the true source of the obstacle:

Is this a skills issue?

The first question I ask myself or the one I’m leading through the struggle is about the skills required to complete the work. I once met with a new leader in my church and delegated him some research. When he reported back to me, the work was disorganized and incomplete. Through some questioning, I realized that he had never analyzed data before, and was not familiar with how to use a spreadsheet. I assumed that he would have learned that in college, and gave him a job that outran his skill set. By helping him learn a new tool, he was then able to be successful at the task.

Is this an experience issue?

The second question I ask myself is about experience. James Thomas said, “To be a great leader and so always master of the situation, one must of necessity have been a great thinker in action. An eagle was never yet hatched from a goose's egg.” A great thinker in action means that leaders are often in new situations, doing new things, in new ways. Especially when we are younger leaders, mistakes are inevitable. If you are finding yourself stuck, ask yourself if you are just inexperienced in this area. An older mentor may be able to give you wisdom on how to handle culture, personalities, or other intangibles that are sometimes difficult to grasp when you are inexperienced in the work.

Is this a character issue?

The final diagnostic question is, “is this a character issue?” As I deconstructed my own failure, I realized that I had said yes to something in the moment that I didn’t actually think was a good idea. I responded to pressure with a hurried “yes” instead of having the courage to say no. I then put off the task and tried to ignore it, because I didn’t believe it was the best course of action. Before I paused to consider the purposes of my heart, I was not aware that I was acting from that motive! I began to realize that what I was struggling with was my own lack of courage, not the actual experience or skills needed for the task. I went back to my teammate and apologized, and learned a great lesson about obstacles.

Whether you are struggling or you are leading someone who is, these questions give you a starting point to understanding obstacles. From there, you can move toward growth in each of those areas:

Skills Issues: What training or tools can help me know how to complete this work?

Experience Issues: Who can come alongside of me as I do this task if I do not have the experience I need to complete well? What margin of error is acceptable in this task, and where do I need to admit my lack of experience is getting me stuck?

Character Issues: How has fear, insecurity, or ego informed my struggle? What is God teaching me through this struggle? What action plan can I put in place to acknowledge and grow through this limitation?

Leadership is challenging enough without condemning ourselves or those we lead in failure. Instead, use this honest assessment—skills, experience, character—to give both you and your team the freedom to grow beyond obstacles and into progress.

Nicole Unice

Nicole Unice is the Assistant Pastor and Director of the Praxis program at Hope Church, a ministry residency program designed to equip new leaders for ministry. Find out more here.


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