I messed up again. It’s the same darn weakness that’s tripped me up for decades.

I get the gist of the college graduation speech maxim: “Seek first to understand, then to be understood.” And in most work and personal situations, I grade high on the first part of that interpersonal principle (when I’m doing the grading, of course). Where I blow it is when it’s my turn to speak, and I have to figure out when the other person really, really understands what I’m saying.

If I’ve taken the trouble to “understand” whatever the other person has to say, why can’t he or she let me know, in some obvious fashion, that he or she is thoroughly absorbing my counterpoint?

So last week, I was on the phone with one of my best friends. Let’s call him Howie—he’ll hate that. We both agreed many years ago that Howie is a wiser, more enlightened person than I’ll ever be. This guy was in all the honors classes. A famous foundation paid for his doctorate and then another famous foundation covered a post doctorate. Howie went into academic research while I went into managing underperforming motels in small towns. Howie was invited to submit his application for President at the same university that had, years earlier, requested I exit their hallowed grounds due to underachievement.

You can see why I might seek out what Howie has to say. It’s probably brilliant.

When we spoke last week, I allowed Howie the first shot at being understood. I turned my phone upside down so I could eat a pretzel while Howie lectured me on my lack of precision in defining corporate strategies. He said it would come back to haunt me and my organization. Howie used a funny term, “multiple perspective analysis,” as the solution to right my corporate leadership and direction. I didn’t cut him off, in part because it was a great pretzel.

After swallowing my last salty bite, it was my turn. I told Howie that I fully understood what he was talking about. Then, I took off explaining my own philosophy of leadership: “management by crisis,” “meander around and engage,” “embrace the shades of gray,” etc. I told Howie that if your head’s on straight with culture and mission within an organization, then the strategic planning and implementation naturally evolve in a robust, exhilarating manner.

Howie said nothing. Not even an “ahuh, ahuh” response. That’s when my bad habit showed up. I felt the need to repeat and repeat my point in all sorts of ways until my victim (Howie) surrendered and somehow let me know that he fully comprehended my position. Now this was a brilliant mind I was speaking to. Objectively, I realized he grasped my thesis before I even had completed my first run-on sentence. But I couldn’t help myself. I kept going. I wanted to know I’d been heard. Howie didn’t need to tell me I was right—I already knew I was. He just needed to convince me he grasped what I had said.

Howie finally cut in on the line and said he had to pick up his grandson from school. I was pretty sure he was lying. He must have been in retreat from my verbal barrage. Howie never gave me any clue that he’d understood what I was saying.

I hung up with him, a little depressed. I’ve screwed up again. So often, it’s hard for me to change for the better.