Early on in my career, I was a beat reporter for newspaper in a small town in Montana, covering the local minor league baseball team.

This was the best job I’ve ever had. If small town sports reporters didn’t get paid in pocket lint and work til 1AM every night, I’d still be doing it.

After the first game I ever covered, I wandered down to the home team clubhouse to interview the manager. He’d been ejected in the 7th inning, and stormed off the field with third base under his arm.  I was both excited and terrified to meet him.

He was sitting on a cooler in his office, wearing just his jockstrap, with a pile of Playboys on his desk and an even larger pile of crushed Miller Lite tall boys at his feet. He was laughing about something with his assistant coaches, but stopped when he noticed me, wiped the foam from his mustache, and tossed me a beer before he ever said a word to me.

I sweated my ass off through that entire 15 minute interview, and the Miller Lite did little to help. I stumbled over statistics and tossed him softball questions because I didn’t know how to ask real ones yet. At the end of it, he said something to me that I’ll never forget.

“You’ve wanted to ask me why I took that base since you walked in here. If you can’t ask the question, how are you supposed to tell the story?”

I’m not sure if he was trying to teach me a valuable life lesson, or if he was just giving me shit because he was buzzed…but after a decade, it still resonates with me.

Over the years I spent in the newspaper and radio industries, I got pretty good at interviews, mostly  because I learned how to work a very specific question into every one of them:

“Why did you do that?”

This question is the key to understanding anything. It is as a journalist, it is as a marketer, and as as a person. Not to delve too deep into marketing jargon, but this is the key to optimization in any situation.

The problem is that we don’t ask this question of ourselves. Just like my first interview in the dirty locker room office, we look for the easy way out.

As a content producer who’s been inducted into the school of data-driven marketing, I spend a lot of time asking “why did I do that?” and “why did that work” of our various campaigns and programs, but it’s much harder to take a step back and ask that of your broader messaging and strategy.

“Why is this what we talk about?” or “Why is that our customer?” or “Why do we say this instead of that?”

These questions are challenging. The answers aren’t easy and they may spit in the face of what we think we know.

But if we can ask “why did I do that?” about the bigger choices and decisions we make every day, we can learn from our mistakes, and our successes, and are able to tell a better, richer story.

Unfortunately, then we need to answer the question honestly, introspectively, and with support…but I’m not your therapist, figure that out on your own.