During my first gig as a manager, I hired a a guy who in a more just world would have been at least three levels above me. He was probably 20 years my senior, triple my experience in the industry, had a master's degree in mathematics and a number of publications, and had done some legitimately hard engineering in his life (assembly programming). I'd spent about eight years building web pages.

However, he'd had the misfortune to be born in the Soviet Union, had emigrated, and was now an older man in an industry that cares not at all about experience from another era. So here I was, his boss.

He had a whole bunch of fantastic stories to tell, was a master ping pong player and an avid mushroom hunter, and for my wedding bought me a bottle of wine which he insisted was Joseph Stalin's favorite brand. But the amazing things about him aren't what I'm here to tell you about.

With all these incredible things about him and unique life experiences, what still sticks out to me about him was watching him use a windowed GUI. I believe we would have been using Windows XP at work at the time; this was 2005, just before everybody I knew switched over to OS X.

I walked by his cubicle one day to check in on how things were going (this was pre-Slack and even pre-Campfire). Usually out of respect I'd try to cough or walk noisily so that people would know I was coming up behind them and not be surprised, but on this particular day he was too absorbed in what he was doing to notice. He was doing the typical web developer dance of changing some code in his IDE, switching to his browser and reloading to see the effect of the change, then switching back.

This was easily accomplished by clicking back and forth between icons in the Windows taskbar; sophisticates knew that Alt-Tab was faster. But what my coworker was doing blew my mind.

He was grabbing the first window and dragging it off the screen until only a few pixels of the corner were visible. Then he'd go grab another window corner sticking in from the other side of the screen and drag that in, realize it wasn't the window he wanted, drag it back, and go hunting.

There were probably fifteen apps arranged this way, just barely poking in to the display area. I watched this for a while, thinking about how massively inefficient it was, and wondering how this was the workflow he ended up with.

He did this every time I observed him using a computer over the course of the next 9-12 months. We'd be talking about code and he'd stop us in the middle for a good couple of minutes so he could go find the window he'd last used.

I mean, this was a smart man, and somebody who'd been involved in computing for a long, long time. My guess is that he'd just spent so long at the command line in his formative years that he couldn't really adapt, and maybe whatever Soviet operating systems he'd worked with had shaped him in a way that made it even harder to change.

Engineers are often exhorted to "learn their tools." I myself did the reverse thing, and finally went and learned to use vim after 14 years as a professional engineer. There's a flip side to that, though, which is that eventually we all start to struggle with learning new things, particularly when we don't see the benefit over the old ways.

Every once in awhile I wonder what I'll struggle with, maybe ten years from now, that some poor twentysomething will have to watch, squirming in impatience and discomfort before finally yelling "Grandpa! Just let me drive."