Okay, so I was tackling a crossword puzzle the other day, you know, just winding down. Got stuck on one clue, it was something like “roger that boss”. Seemed simple enough at first glance, right? But my mind just drew a blank for a bit.

Figuring it Out
First thing I did was break it down. “Roger that” – easy peasy, means “Okay, I understand,” or “affirmative.” Then “boss” – leader, chief, supervisor, the person in charge. So, the answer should mean something like “Okay, boss” or “Understood, chief.”
I started mentally listing possibilities based on how many letters I thought I needed – didn’t have many crossing letters filled in yet, which made it trickier. My first thoughts were things like:
- OKAY BOSS – Too long, usually.
- GOT IT CHIEF – Definitely too long.
- AFFIRMATIVE – Way too long and doesn’t include the “boss” part directly.
Then I thought about where you might actually hear “roger that”. Radio talk, military stuff, pilots maybe. That led me to think about formal acknowledgements to a superior. “Aye aye, captain!” popped into my head. Captain’s a kind of boss, right? “AYE AYE” could fit, maybe? Sometimes crosswords use that. It felt close.
But I kept circling back to the “boss” part. It felt important. It wasn’t just “roger that,” it was specifically to the boss. What’s a really common, maybe slightly formal or traditional way to say “yes” to a superior?
The Breakthrough
I pictured someone in uniform, maybe. What would they say? And then it clicked. YESSIR! It fit the meaning perfectly: “Yes” (like “roger that”) and “Sir” (acknowledging the boss/superior). I quickly counted the letters in my head – six. Checked the grid space again. Yep, six squares. Felt pretty good about that one.
Filled it in, and later on, the crossing words confirmed it. Pretty satisfying when you wrestle with a clue like that and finally nail it down. Just had to combine the two parts of the clue and think about the context where you’d actually say it.