Roscoe Poses the Problem: How Late Are You Gonna Be?

We've previously made the acquaintance of Roscoe Leroy,^[1] a crusty old retired mining engineer. It was a dismal, rainy day when he pulled up in front of the house, running from his pickup to the front door, his slicker flapping in the wind. "Here comes the sun," I thought to myself.

^[1] See Chapter 5, "The Most Important Thing," and 10, "Estimating," for more background in case you are reading the book out of order and this is your first contact with Roscoe.

As you may recall, Roscoe is an old war buddy of my dad and has a wealth of real-world experience from the school of hard knocks and cruel treatment. The reason I listen to Roscoe is that he brings a fresh perspective to anything he looks at, and his thinking is not overly encumbered by conventional wisdom, accepted doctrine, or theoretical considerations. My sources tell me that he has saved more than one engineering manager's bacon in the course of his "career."^[2]

^[2] If you asked Roscoe, he would scoff at the notion of a "career." "Just trying to get the job done, son," is what he would usually say when asked about any of his accomplishments or failures.

"So," I led off, "how's the new career in managing software development going?"

"Well, what we have here is a failure to communicate,"^[3] Roscoe started off. The road boss's reflecting sunglasses from Cool Hand Luke flashed before my eyes when he started that way. I hoped this would end better than in the movie.

^[3] Famous quotation, often repeated, from the movie Cool Hand Luke, starring Paul Newman.

"In the first place," he said, "software projects are always late. And I mean always. That just doesn't seem right. After all, most estimates of pretty much everything else have an error that is stated as 'plus or minus such-and-such.' In software, you people seem to have lost the 'minus.' The estimator might just as well say 'This is the best we think we can do.'"

I admitted that his observation seemed to be mostly correct. Roscoe excoriated me for the "mostly." He defied me to show him one project that had been completed early. I squirmed. I did remember a milestone being early once, but a whole project…

"So, it would seem to me that the problem in calling the shot is to figure out just how late you are going to be," he said, smiling.