You have most likely already heard that asking “why” five times will lead you to the root cause — or at least help you gain a deeper understanding of a particular situation. Some fleet managers may be rarely challenged, but I would argue most are. As I have come to learn over the last few years, anticipating questions you may receive from your superiors or organizational leadership will always make you better prepared.   

I had an interesting experience the other day that had nothing to do with work. I was driving my daughter to practice and she asked me a simple question to which I thought I had a simple answer. She pondered my response, and a few seconds went by before she followed up with, “Well, WHY, daddy?”

I would be lying if I told you I remembered the question she asked, but I do remember scrambling for an answer that I thought could diffuse the situation. Then it happened again: “Why?” my daughter asked. At this point all I could hear in my head was, “Abort! Abort mission! Houston we have a problem.”

It was at this moment that something amazing happened; I found a distraction to change the topic of conversation. Oddly enough, it summarized the situation.

“Look Sofia! The street is broken right there, and you can see the really old street is made of bricks.”

“Cooooool,” she said as we drove by it, and that was the end of the whys — for the moment.

That broken road that exposed the past was just a few inches below the surface. Oftentimes, not punching through this proverbial “surface” can make us appear unprepared. Looking for what lies beneath can help you understand why or help you be equipped to answer some questions — or better yet, proactively address questions that people are thinking but haven’t asked yet.

Asking why helps you prepare, improve, or just understand a situation better. Next time, try asking yourself or your team “why.”